Brooke & Jeffrey — Second Date Update

Second Date Update: Float & Boat

Wed, 28 Oct 2026 15:05:00 +0000

One of our listeners was SO RELAXED on her night out with Vince, that she did something unintentional and kind of embarrassing. She thinks it’s probably why she needs our help with a Second Date Update!

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Second Date Update: Haunted House Hero

Mon, 26 Oct 2026 15:25:00 +0000

One of our listeners said he met a woman during the spookiest time of the year but he never expected to be GHOSTED! We’re investigating and digging in for him in your Halloween Second Date Update!

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Second Date Update Classics: Dutch Isn't Just A Language + Dry Lips & Hands On Hips

Sat, 24 Oct 2026 12:30:00 +0000

Part 1

Jake and Kim bonded on their date over their shared HATE for one specific thing… But now she’s not calling back? Maybe we can get her to explain coming up in your Second Date Update!

Part 2

All Anthony had to do to make himself PERFECT for his date is change TWO PHYSICAL things about himself…and of course it completely backfired.

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Second Date Update: Apple Picking For The 1 Percent

Fri, 23 Oct 2026 15:05:00 +0000

Daniel was DESPERATELY trying to avoid answering one specific question on his date with Lilly. It got asked, it DIDN’T go well, and now he wants our help figuring out how to put the pieces back together in your Second Date Update!

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Second Date Update: Microwaved Salad Guy

Wed, 21 Oct 2026 15:05:00 +0000

One of our listeners has a crush on his co-worker and he came up with a plan to show her! It involves a microwave and a wilted bowl of salad…

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Second Date Update: Food Court Cutie

Mon, 19 Oct 2026 15:30:00 +0000

Susan said her date asked her a STRANGE question at the end of the night and was VERY disappointed by her response… You’ll hear the question and her answer in your Second Date Update!

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Second Date Update Classics: Bathroom 911 + Big Fajita Energy

Sat, 17 Oct 2026 12:30:00 +0000

Part 1

Nick is willing to tell us the MOST EMBARRASSING date night of his life… in hopes it will get him another shot with the woman he loves. Will it be worth the humiliation?

Part 2

We have NO IDEA who we’re dialing in today’s Second Date Update, we have a number, and a sneaking suspicion it might be a trap but only one way to find out!

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Second Date Update: Vacation On Me

Fri, 16 Oct 2026 15:05:00 +0000

Kyle made ONE SLIGHT adjustment to his dating profile and he ended up matching with a woman he calls “The real deal.” So why does he need our help? We’ll figure it out in your Second Date Update!

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Second Date Update UPDATE: A Whole New Girlfriend

Thu, 15 Oct 2026 15:15:00 +0000

You may remember Brian and Olivia as a “Disney DO & Disney DON’T” couple where he was super into all things Disney and she was open to learning more…. But where are they now MONTHS after they first appeared on the show? Find out in your Second Date Update UPDATE!

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Second Date Update: The Sobfather

Wed, 14 Oct 2026 15:35:00 +0000

What’s the most embarrassing thing your date could catch you doing? David got caught at a bad time RIGHT as his date was meeting up with him and it happened AGAIN later on. We’ll help him try to recover in your Second Date Update podcast!

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Second Date Update: McLaren Missus Mishap

Mon, 12 Oct 2026 15:05:00 +0000

In today’s Second Date Update we found ourselves in the middle of a problem that is WAY out of our price range, even Brooke’s!

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Second Date Update Classics: Hotel Bar Rendezvous + Facebook KO

Sat, 10 Oct 2026 12:30:00 +0000

Part 1

5 minutes into his date with Delilah, Jack realized he forgot something MAJORLY important. Hear what slipped his mind and how we’re helping him gain back ground!

Part 2

The listener in today’s Second Date Update says that if we can’t help him, it’ll be the first time EVER that he’s been rejected by a woman!

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Second Date Update Classic: Burned By Beauties

Fri, 09 Oct 2026 13:20:00 +0000

When we offered to send this couple on another date that WE PAY for, we never expected to get the answer back that we received. Hear one of the most bizarre endings to a Second Date Update ever!

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Second Date Update: Seven Foot Date

Wed, 07 Oct 2026 14:59:00 +0000

Brian had so much fun on his date with Ariel, that at one point they were feeding each other food like animals! So, why isn’t she calling him back for more animal-style love? We’ll find out in your Second Date Update podcast!

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Second Date Update: Dating Is Such A Chore

Mon, 05 Oct 2026 15:10:00 +0000

Mike and Chrissy’s first date sounded like the start of a horror movie… Why was a mysterious stranger watching them silently the whole time?? We needed more details in the Second Date Update podcast!

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Second Date Update Classics: Mystery Treadmill Man + Till Date Do Us Part

Sat, 03 Oct 2026 13:00:00 +0000

Part 1

The woman in today’s Second Date Update agreed to meet up with a man before she even knew his name, and it’s all because of one grand romantic gesture.

Part 2

For one of our listeners, the hottest thing that happened on her date was a game of CHARADES!

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Second Date Update: G-Wagon Naggin'

Fri, 02 Oct 2026 15:15:00 +0000

Hannah says that she and her date got into TWO arguments before they even got out of her driveway! Why would she even want to see him again? She’ll explain in your Second Date Update podcast!

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Second Date Update UPDATE: Universe Is Busy Right Now

Thu, 01 Oct 2026 15:25:00 +0000

Out of all the Second Date Updates we’ve done in 2026, this one might have been the most viral! And we’ve got the couple back for a long awaited Second Date Update UPDATE!

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Second Date Update: The Muffin Lady

Wed, 30 Sep 2026 15:05:00 +0000

Vince is on the phone for a Second Date Update and he says the intimate parts of his relationship with Jamie are great but he want’s our help getting MORE SERIOUS than he’s ever been before!

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Second Date Update: Third Wheel Steal

Mon, 28 Sep 2026 15:05:00 +0000

The guy on the phone for today’s Second Date Update isn’t getting a call back, and it’s probably because the woman he’s interested in was on a DATE with ANOTHER MAN! He swears he can explain in the podcast!

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Second Date Update Classics: Mothers Dayte + Terrible Tarot

Sat, 26 Sep 2026 13:00:00 +0000

Part 1

The guy on the phone today decided he would surprise his date with an unexpected guest during their dinner… Hear who it was in the podcast!

Part 2

The guy in today’s Second Date clearly got his idea for a date from listening to our show, and we might owe him an apology, or at least some help trying to get another one!

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Second Date Update: Unwritten Rules For Fools

Fri, 25 Sep 2026 15:10:00 +0000

Jack managed to secure a night over at Sarah’s place, but she CAUGHT HIM on the couch doing something he shouldn’t in the MIDDLE of the night! Find out what happened in your Second Date Update!

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Second Date Update: Drive Thru Date

Wed, 23 Sep 2026 15:05:00 +0000

Cody admits “MISTAKES WERE MADE” on his date with Tiz. But, despite his failings he’s ready to reach out and try to make a better love connection in your Second Date Update podcast!

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Second Date Update: Bump Set Date

Mon, 21 Sep 2026 15:05:00 +0000

Tracy gave Rob a VERY specific place he had to go in order to score a date with her. Was it worth his effort? Let’s find out in your Second Date Update podcast!

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Second Date Update Classics: Coffee Club + Falling to Pieces

Sat, 19 Sep 2026 13:00:00 +0000

Part 1

One of our listeners did something THREE different times during their date… and while once might be strange, at the end it all made sense.

Part 2

One of our listeners admits SHE did something stupid, just to MEET a guy. Was it her idea? No. Was it effective? Let's find out!

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Second Date Update: YeeHaw or YeeNaw

Fri, 18 Sep 2026 15:05:00 +0000

Beth is regretting rejecting Eddie, who happened to be wearing a certain “fashion accessory” and now she wants a do-over! We’ll see what magic we can work in your Second Date Update podcast!

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Second Date Update: Tour of the Town

Wed, 16 Sep 2026 15:05:00 +0000

The guy in today’s Second Date Update secretly planned a very informative and special date night for the woman he’s interested in. It’s one of the MOST ORIGINAL date ideas we’ve ever heard.

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Second Date Update: Buttery Smooth

Mon, 14 Sep 2026 15:15:00 +0000

The woman in today’s Second Date Update knows she didn’t give strong signals to the guy she’s interested. In fact, she stayed FAR AWAY from him the whole night! We’ll dig into why in your Second Date Update podcast!

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Second Date Update Classics: Singles Mixer Shocker + Up Up & Run Away

Sat, 12 Sep 2026 13:00:00 +0000

Part 1

One of our listeners came up with one of the CLEANEST & MOST FUN ice breaker questions we’ve ever heard…

Part 2

The woman on the phone today described her date like a very famous film, but the comparison immediately had us all very concerned.

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Second Date Update: Love At First Like

Fri, 11 Sep 2026 15:15:00 +0000

SOMEONE drops the “L-word” on today’s upcoming Second Date Update and the only thing weirder than them saying it, is what happened the next day!

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Second Date Update UPDATE: Hired A Hinge Coach

Thu, 10 Sep 2026 15:05:00 +0000

SPEED was definitely a factor in Roman and Hailey’s blossoming relationship when they were first on our show months ago. But, today they’re back to fill us in and what’s happened since then in a Second Date Update UPDATE!

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Second Date Update: A Mop To Remember

Wed, 09 Sep 2026 15:15:00 +0000

One of our listeners tried a new way to meet single guys in real life, and she found herself in a dark room FULL of eligible bachelors! Hear about the surprising guy that she connected with in your Second Date Update!

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Second Date Update Classic: Lapping Up Love

Mon, 07 Sep 2026 13:20:00 +0000

What one of our listeners did in a public park during her first date was definitely FREAKY. So much so, that it had us in studio wilding out!

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Second Date Update Classics: Good Not Great Date + Most Malone

Mon, 07 Sep 2026 05:20:00 +0000

Part 1

Abbey had dates with TWO different guys, but could only pick one to pursue. Did she choose correctly?

Part 2

Miles’s closing move with Zoey was not only fun and flirtatious, it also comes with pizza. We guarantee guys are gonna try and steal this…

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Second Date Update Classic: Zoo Zaddy

Fri, 04 Sep 2026 15:05:00 +0000

One of our listeners felt INSTANT REGRET during his date and even tried to BAIL as soon as it started… But he stuck it out and now he wants our help with a Second Date Update!

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Second Date Update: Gammy's Bar Crawl

Wed, 02 Sep 2026 15:10:00 +0000

Not all surprises are good surprises, and one of our listeners found that out the hard way! Hear what kind of trouble Ava and Dean found themselves in, in your Second Date Update podcast!

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Second Date Update: Bobby 2.0

Mon, 31 Aug 2026 15:30:00 +0000

Bobby didn’t come across in the best way the FIRST time he was on our show, but this time he SWEARS he’s changed and is now deserving of our help with a Second Date Update!

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Second Date Update Classics: Only Tears + 22nd Date Update

Sat, 29 Aug 2026 13:00:00 +0000

Part 1

One of our listeners isn’t sure if his date meant to VANISH or if there was just miscommunication but you can tell us what you think after you hear it.

Part 2

Today we’re shaking it up and doing an ALTERNATE version of our Second Date Update… Going to levels we’ve never gone to before!

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Second Date Update Classic: First Date Worth The Wait

Fri, 28 Aug 2026 13:15:00 +0000

The guy in today’s Second Date was willing to do something that took A LOT of patience, selflessness, and understanding… hear if his sacrifice was worth it in the podcast!

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Second Date Update Classic: Secret Garden Shocker

Wed, 26 Aug 2026 13:15:00 +0000

In today’s Second Date we learned about a dating app that NONE of us had even heard of before, and even though we were skeptical.. it helped one of our listener's secure his match!

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Second Date Update Classic: How Dare You Heart Me

Mon, 24 Aug 2026 13:15:00 +0000

One of our listeners says he got a singular one-word text that let him know he BADLY screwed up his first date.

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Second Date Update Classics: I Got Cheesecaked + Locked Out Of Love

Sat, 22 Aug 2026 13:00:00 +0000

Part 1

Cory took a PLANE FLIGHT to hang out with Alison… but their date left a lot to be desired… We’ll try to fix their future in your Second Date Update podcast!

Part 2

One of our listeners took a BOLD step when she made a move on a guy while he was working… and seconds later they were inside her place getting familiar.

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Second Date Update: A Note For the Waitress

Fri, 21 Aug 2026 15:05:00 +0000

Sasha is on the phone for today’s Second Date Update and she thinks the guy who left her his number is either her soulmate or a COMPLETE Scum Bag! Lucky for her, we've got a very special way to unveil the truth…

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Second Date Update UPDATE: Not So Spicy

Thu, 20 Aug 2026 15:12:10 +0000

Aria and Ryan managed to do the near impossible: start a romance thanks to our show! And now they’re BACK and you’ll find out what’s happened since they were last on thanks to a Second Date Update UPDATE!

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Second Date Update: I Went Full Robbins

Wed, 19 Aug 2026 15:10:00 +0000

One of our listeners wanted to show his date he was a fun, outgoing guy, but what came out of his mouth is one of the CRINGIEST moments we’ve ever heard happen on a date!

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Second Date Update: Smells Like A Hamster

Mon, 17 Aug 2026 15:15:00 +0000

One of our listeners says he has the PERFECT question that will tell him whether to STICK AROUND or RUN on a first date. Hear what it is in your Second Date Update podcast!

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Second Date Update Classic: Yawn and She's Gone

Fri, 14 Aug 2026 15:05:00 +0000

We’ve reached a pretty insane milestone with today’s Second Date and it happened with one of the nicest guys we’ve ever had on the show.

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Second Date Update: Sushi & Steve

Wed, 12 Aug 2026 15:05:00 +0000

The “move” Sophia pulled at a restaurant on her date with Steve would either get you a second date OR get you kicked out of the building forever. Hear what it was in your Second Date Update podcast!

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Second Date Update: Surprise Surprise

Mon, 10 Aug 2026 15:35:00 +0000

One of our listeners got one of the BEST compliments a guy could get from a girl at the end of the night, but he’s PUZZLED why she’s not calling him back! We’re on the case in your Second Date Update podcast!

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Second Date Update Classics: Floral Intentions + Lipstick Dipstick

Sat, 08 Aug 2026 13:00:00 +0000

Part 1

One of our listeners tried out the dating app PLENTY OF FISH… and you’re not gonna believe what happened on her very first meet up!

Part 2

One of our listeners WISHES he did a better job cleaning up his car, because his entire night was ruined when his date found something between his seats. Find out what the incriminating item was in the Second Date Update podcast!

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Second Date Update Classic: Second Chance Scott

Fri, 07 Aug 2026 13:30:00 +0000

One of our listeners went on a beach date and he gets huge props for one thing he DIDN’T DO… what was it? Find out in your Second Date podcast!

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Second Date Update: Movie Mayhem

Wed, 05 Aug 2026 15:35:00 +0000

A date at the movies went from your typical rom-com setting to an absolute HORROR scenario and now Sienna wants our help getting Evan to call her back!

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Second Date Update: Kiss GPT

Mon, 03 Aug 2026 15:45:00 +0000

What’s the best way to get better at kissing? Is it just practice and experience? Or is there an expert out there that’s much closer than you might think? We’re answering that question in your Second Date Update podcast!

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Second Date Update Classics: Soulmate Psychic + Can I Cut In Lime

Sat, 01 Aug 2026 13:00:00 +0000

Part 1

One of our listeners had a great first encounter with his date, but it was his FIRST TEXT after it ended that wrecked things…

Part 2

A single phone call caused the guy in today’s Second Date Update to RUN OFF on his date with someone he called one of the most beautiful women he’s ever met!

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Second Date Update UPDATE: Does This Smell Like Ur Mom?

Thu, 30 Jul 2026 15:05:00 +0000

Denise and Caleb were on our show late last year and we got TONS of texts asking to follow up with them. We did and now they’re back to tell us all the romantic details that have happened since! It's a Second Date Update UPDATE!

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Second Date Update: Mom Blocked

Wed, 29 Jul 2026 14:59:00 +0000

David brought Anne back to his place after their date, and when the front door randomly opened he was greeted by a grown man’s worst nightmare! Hear how it all went down in your Second Date Update!

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Second Date Update: Nanny No No

Mon, 27 Jul 2026 15:10:00 +0000

Katrina spent the last 20 minutes of her date with Raymond LOCKED in her car by herself. Why would she do that? There’s a reason and you can hear it in the Second Date Update!

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Second Date Update Classics: Hearts & Crafts + One More Refill

Sat, 25 Jul 2026 13:00:00 +0000

Part 1

One of our listeners discovered a little trick to exchange phone numbers with someone in public without uttering a SINGLE WORD… and the ladies seem to love it!

Part 2

A request made at a dinner date might have crossed the line… but Kard says he was well within his rights on his date with Amy! Hear how it went down in your Second Date Update.

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Second Date Update: Special Friend Fun

Fri, 24 Jul 2026 15:15:00 +0000

Dating has become so complicated & expensive… where if you DON’T FEEL IT in the first 30 seconds… there’s NOW a sentence you can say…. that gives you an instant FREE PASS to get out of it… It happened to one of our listeners in today’s Second Date Update!

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Second Date Update: Jiu-Jitsu and Chill

Wed, 22 Jul 2026 15:55:00 +0000

If your date ditches you in the middle of dinner is there ANY valid excuse that could earn forgiveness? It happened to Tara and now she wants our help figuring out why Norris ran out on her, in your Second Date Update!

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Second Date Update: Greek Meat

Mon, 20 Jul 2026 15:25:00 +0000

A romance blossomed out of the ashes of a once-thought to be dead dating app… but then it all came crumbling down at a fancy Greek restaurant. We got the juicy details coming up in your Second Date Update podcast!

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Second Date Update Classics: Offer He Can't Refuse + Sea Meat Surprise

Sat, 18 Jul 2026 13:00:00 +0000

Part 1

One of our listeners says a DEAFENING silence happened after an awkward question from their waiter on their date, and now she’s not getting a call back.

Part 2

The woman on the phone today claims that she discovered a place that is swarming with career driven, high-value men, and she even scored a date on her first visit. The problem? He's not calling her back!

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Second Date Update: Bidding On Brandy

Fri, 17 Jul 2026 13:30:00 +0000

How far would you go to win over a beautiful woman who showed interest in you? One of our listeners went to the EXTREME and he might have gone too far because now he wants our help with an Second Date Update!

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Second Date Update: Case of the Solo Shoe

Wed, 15 Jul 2026 15:05:00 +0000

We have a real-life Cinderella story on our hands today! Will has one of Teri’s SHOES after their night out and in your Second Date Update we’re gonna find out why she left it and why she’s not calling him back!

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Second Date Update: Car Wash Crush

Mon, 13 Jul 2026 15:10:00 +0000

One of our listeners says she found an UNDERRATED place for ladies to meet QUALITY guys… and it might shock you where.

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Second Date Update Classics: Randall Is Back + Highs & Lowells Of Dating

Sat, 11 Jul 2026 13:00:00 +0000

Part 1

After many failed romantic encounters and a couple of outright scams, one of our most lovable listeners is back! He says this time is different because he finally executed the perfect date night...at least for a few minutes. We'll find out what went wrong this time!

Part 2

Tara says MATH of all things helped her meet the perfect guy… You can hear how in your Second Date Update!

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Second Date Update: Anti-Farmers Market

Fri, 10 Jul 2026 15:05:00 +0000

Sam took Jamie to a UNIQUE first date spot. In fact, it was so unique, its not only impressive but it became it’s own conversation piece. We guarantee you’ve never heard of this date idea before!

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Second Date Update UPDATE: He Bought Me A Star

Thu, 09 Jul 2026 15:05:00 +0000

We’re bringing back a HIGHLY REQUESTED couple that have been on our show before, to get all the out-of-this-world details of what’s happened since they last talked with us. It’s a special Second Date Update UPDATE!

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Second Date Update: Tap It or Scratch It

Mon, 06 Jul 2026 15:20:00 +0000

Andre managed to cancel plans on Kim NOT ONCE, but TWICE in the same night. Is that too much to come back from? Find out in your Second Date Update podcast!

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Second Date Update Classics: B Dub Flub + Red Light Green Light

Sat, 04 Jul 2026 13:00:00 +0000

Part 1

When the woman on the phone today described her job to us we were SHOCKED… but is it something that would keep her from a happy dating life?

Part 2

In today’s Second Date Update there was one moment that brought the evening to a SCREECHING HALT!

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Second Date Update Classic: I Brought My Mom

Fri, 03 Jul 2026 13:30:00 +0000

What the couple on the phone today went through on their date was JUST SHORT of the plot of a James Bond movie. Were they shaken or stirred? We’ll find out in your Second Date Update!

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Second Date Update Classic: Uber Meets

Wed, 01 Jul 2026 13:30:00 +0000

One of our listeners says HER MOM may have accidentally ruined her chance with a guy and its all because of what mom needed from her daughter in the MIDDLE of a date.

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Second Date Update Classic: Dine For One But I'm Not Done

Mon, 29 Jun 2026 13:30:00 +0000

The listener on the phone says her date ended up with some unexpected extra guests… but it’s actually kind of sweet how it all came together. Hear what happened in a Second Date podcast!

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Second Date Update Classic: Not A Happy Camper

Fri, 26 Jun 2026 15:05:00 +0000

One of our listeners botched her date after trying to give him an honest compliment…. Hear how we tried to help her out her problem in a Second Date Update!

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Second Date Update: Pursue Me Please

Wed, 24 Jun 2026 15:05:00 +0000

Sometimes in the dating world, you have to decide if the pursuit is WORTH the prize at the end of the journey. In today’s Second Date Update we’re figuring out just HOW FAR one man will go for just one, single date.

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Second Date Update: Tamogatchi Tea

Mon, 22 Jun 2026 15:20:00 +0000

One of our listeners told us he was STRUGGLING to get his date back on track after a few early fumbles, until a COMPLETE STRANGER swooped in and changed everything with one simple sentence!

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Second Date Update Classics: Failure To Launch + CSI Dinner Investigation

Sat, 20 Jun 2026 13:00:00 +0000

Part 1

Can a guys job be a red flag? The woman in today’s Second Date met her guy at his red flag job, and she decided against her better judgment to go after him anyway!

Part 2

Samantha warned her date that there’s ONE THING he HAD to do before she would see him… and he was shocked to find out she was SERIOUS.

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Second Date Update Classic: I Dare You To Date Me

Fri, 19 Jun 2026 13:30:00 +0000

One of our listeners got maybe the worst possible response to an unsolicited text message… EVER!

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Second Date Update: Stroll Club Hero

Wed, 17 Jun 2026 15:05:00 +0000

Josh tried to be funny to impress Lisa on their date and that plan BACKFIRED so badly, he found himself apologizing to a random 9 year old and his family. Hear how his humor got him in trouble in your Second Date Update podcast!

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Second Date Update: Shark Tanked

Mon, 15 Jun 2026 15:15:00 +0000

One of our listeners took his date to a ball game and INSTANTLY she was set off on a bad mood. He doesn’t know what sparked it but we’re on his side and we’re gonna dig in, when we do a Second Date Update!

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Second Date Update Classics: Big Fragrance Energy + Trying To Connect 4

Sat, 13 Jun 2026 13:00:00 +0000

Part 1

One of our listeners is worried her gratitude for a gift was BADLY misinterpreted as rude and now she wants our help with a Second Date Update!

Part 2

What do you do when someone suddenly STOPS replying to your texts? One of our listeners did something a little UNUSUAL to get his crush’s attention.

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Second Date Update: No Questions Ever

Fri, 12 Jun 2026 15:05:00 +0000

One of our listeners has a SYSTEM to get a date with ANY woman you want. But some of his tactics were so controversial, it nearly BROKE Brooke!

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Second Date Update UPDATE: First Base Fam

Thu, 11 Jun 2026 15:05:00 +0000

We’ve had “Momma’s boys” and women with “Daddy Issues” on our show before but today we’re reconnecting with a DIFFERENT type of Red Flag that involves a third type of family member… It’s a special Second Date Update UPDATE where if you listen until the end we check in with the couple and how things have gone since they first appeared on our show!

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Second Date Update: Too Pretty To Tip

Wed, 10 Jun 2026 15:35:00 +0000

Andrew overheard two woman saying something so SHOCKING & RUDE that he had to step in. He thinks he was heroic, but was it actually creepy?

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Second Date Update: Big Brain vs Semicolon Corey

Mon, 08 Jun 2026 15:15:00 +0000

One of our listeners says the woman he went out with wanted something VERY SPECIFIC whispered into her ears and it had him thinking “This woman is THE ONE!” Find out what that was coming up in your Second Date Update podcast!

See omnystudio.com/listener for privacy information.

Second Date Update Classics: Brunch Yuck + Down Under Blunder

Sat, 06 Jun 2026 13:00:00 +0000

Part 1

Rez DEFINITELY regrets a story he told Katrina on their date, and you’re gonna want to hear how he tells it in the Second Date Update!

Part 2

One of our listeners is looking for all the help he can get locking down another hang out with a VERY classy woman.

See omnystudio.com/listener for privacy information.

Second Date Update: Three Day Bouquet

Fri, 05 Jun 2026 15:15:00 +0000

Is a gift ever okay on the first date? Does it say too much or go too far? We go to the bottom of that question and got way more than we bargained for in your Second Date Update podcast!

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Second Date Update: Capes At Costco

Wed, 03 Jun 2026 15:05:00 +0000

We’ve heard some strange dealbreakers before on this show, but NOTHING has us as confused as the dealbreaker Kai had for Amy in today’s Second Date Update!

See omnystudio.com/listener for privacy information.

Second Date Update: Door Dash Ashley

Mon, 01 Jun 2026 15:30:00 +0000

Blake didn’t spend ANY money on his date with Ashley, in fact, he actually MADE money in a way that’s 100% legal. You’ll hear how in your Second Date Update podcast!

See omnystudio.com/listener for privacy information.

Second Date Update Classics: No Fire In The Fireplace +Best Date Of My Life

Sat, 30 May 2026 13:00:00 +0000

Part 1

One of our listeners realized she’s been approaching dating apps the wrong way… and one piece of advice completed shifted her romantic life.

Part 2

The kiss that happened at the end of our listener's date was either the cutest, most spontaneous thing ever, or the cringiest, most awkward interaction of all time. Decide for yourself after the Second Date Update!

See omnystudio.com/listener for privacy information.

Second Date Update: Can't Beat The Sweet Treat

Fri, 29 May 2026 15:10:00 +0000

One of our listeners showed up to his co-workers “DIVORCE PARTY” and while the theme was a bit strange, the romance levels were surprisingly high and now we’re gonna help him get ahold of the woman he met there in your Second Date Update!

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Second Date Update UPDATE: Euro Date

Thu, 28 May 2026 15:10:00 +0000

Two of our listeners told us about “European Dating” and it led to one of the most popular Second Date Updates of the year! Now, they’re back on again for a special UPDATE UPDATE!

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Second Date Update: Defensive Driving Drama

Wed, 27 May 2026 15:15:00 +0000

Jay let Allie know IMMEDIATELY what ONE THING has been a deal breaker, about his past… He thought she would appreciate it, but now he’s asking us for a Second Date Update!

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Second Date Update Classic: Senior Moment Slip Up

Mon, 25 May 2026 13:30:00 +0000

One of our listeners admits she broke more than FIVE unwritten rules of dating, but she says she had a good reason too!

See omnystudio.com/listener for privacy information.

Second Date Update Classics: Update My Dino Profile + Doodle Worthy

Sat, 23 May 2026 13:00:00 +0000

Part 1

One of our listeners went down a weird internet rabbit hole and what she found changed her whole approach to dating… Hear what she learned in your Second Date Update!

Part 2

The guy on the phone today tried a UNIQUE STRATEGY to extend his date.… and even he admits, it was WAY more cringe than he thought it would be…

See omnystudio.com/listener for privacy information.

Second Date Update Classic: Train Game

Fri, 22 May 2026 13:30:00 +0000

There’s no EASY way to approach an attractive person on public transportation, and that was exactly the case for our listener! She’ll tell us her story and how she wants to get in touch with a guy she met on the train coming up in a Second Date Update!

See omnystudio.com/listener for privacy information.

Second Date Update: The Roadside King

Wed, 20 May 2026 15:05:00 +0000

One of our listeners says he DEFINITELY has someone to thank for his unforgettable date night. But the weird part is… that person isn’t exactly ALIVE…

See omnystudio.com/listener for privacy information.

Second Date Update: Mistaken Identity

Mon, 18 May 2026 15:20:00 +0000

Our listener on the phone today went out of his way to do the KIND, HONEST, and RESPECTFUL thing for his date… but it ended him up here with us and out of luck and love! Luckily, we can help him with a Second Date Update!

See omnystudio.com/listener for privacy information.

Second Date Update Classics: I've Dated My Date Before + Two Word Whisperer

Sat, 16 May 2026 13:00:00 +0000

Part 1

One of our listeners had the SHOCK OF A LIFETIME after being set up on a blind date by her friend. As soon as she showed up she knew something was very wrong…

Part 2

The woman on the phone today says her date decided to switch booths HALFWAY through their dinner… And all of us were stunned when we finally learned the actual reason he demanded to move locations.

See omnystudio.com/listener for privacy information.

Second Date Update: Ramen Common

Fri, 15 May 2026 15:05:00 +0000

The woman on the phone today shared a SHOCKING secret in today’s Second Date Update. We were cool with it at first but by the end of the call our jaws were on the floor!

See omnystudio.com/listener for privacy information.

Second Date Update UPDATE: Numbers Don't Lie But You Should

Thu, 14 May 2026 15:15:00 +0000

Ashwin and Sierra came on our show a while back and we got SO many comments asking for more info, we HAD to bring them back for a Second Date Update UPDATE! Stay tuned to the end to hear from both of them and how their romance has gone since last time they spoke with us!

See omnystudio.com/listener for privacy information.

Second Date Update: Corpse Kiss

Wed, 13 May 2026 15:05:00 +0000

One of our listeners refused to do things the easy way, and after he complicated drinks with his date, he thinks he knows the reason she’s not calling him back! We’ll see if he’s right in your Second Date Update podcast!

See omnystudio.com/listener for privacy information.

Second Date Update: Strawberry Blowout

Mon, 11 May 2026 15:50:00 +0000

Our listener on the phone thinks that the reason he's not getting a call back is because of an argument he got into with a cashier during their date. He says it’s totally justified but he wants our assistance explaining! We'll do just that in the Second Date Update Podcast!

See omnystudio.com/listener for privacy information.

Second Date Update Classics: Flea Market Find + Due The Math

Sat, 09 May 2026 13:00:00 +0000

Part 1

Our listener on the phone today says his date set a boundary before they even met in person. He had to say “yes,” to get a shot at her, and now we’re trying to get her to say “Yes” to a Second Date!

Part 2

We promise you that you’ve never heard of anything like the move a guy pulled to ask out our listener outside a coffee shop.

See omnystudio.com/listener for privacy information.

Second Date Update: Taylor Where'd Ya Go

Fri, 08 May 2026 15:10:00 +0000

Dennis wrote a SONG for Taylor after their night out and he’s not getting a call back. In exchange for our help with a Second Date Update he’s gonna let us PLAY IT on air too!

See omnystudio.com/listener for privacy information.

Second Date Update: French Air Kiss

Wed, 06 May 2026 15:05:00 +0000

Our listener invited herself along to run errands with her date and they actually had a pretty great time! But something about his dating profile is making her uneasy… Find out what that is in the Second Date Update podcast!

See omnystudio.com/listener for privacy information.

Second Date Update: Potter Got Hotter

Mon, 04 May 2026 15:05:00 +0000

The guy on the phone today pulled out the stops to take his date to a staged play, and even though the PLAY was magical, his evening must have been less than because he’s not getting a call back.

See omnystudio.com/listener for privacy information.

Second Date Update Classics: 1st Impression Means Everything + Dino Drunkfest

Sat, 02 May 2026 13:00:00 +0000

Part 1

One of our listeners invited her date back to her place and spent HOURS together… but what she saw him do… she’s STILL trying to process.

Part 2

Today’s Second Date Update is all about the 3 D’s – Dinosaurs, drinking and diamonds. Hear the call for yourself in the podcast!

See omnystudio.com/listener for privacy information.

Second Date Update Classic: Where Do I Know You From?

Fri, 01 May 2026 13:30:00 +0000

A weird little mix-up at the airport turned out to be a GOLDEN OPPORTUNITY FOR LOVE… You’ll hear about one of our listeners and his lucky accident in a Second Date Update!

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Second Date Update: Practice Makes Perfect

Wed, 29 Apr 2026 15:10:00 +0000

The guy on the phone today says there’s ONE THING about his date that might give 99% of dudes “the ick” but it actually TURNS HIM ON. You’ll hear what it is in your Second Date Update!

See omnystudio.com/listener for privacy information.

Second Date Update: Glad You Didn't Die

Mon, 27 Apr 2026 15:45:00 +0000

Our listener on the phone says his night ended with his date telling him “I’m glad you didn’t die.” It was a close call but he’s here with us for a Second Date Update!

See omnystudio.com/listener for privacy information.

Second Date Update Classics: Barwreck + Meal Me Once

Sat, 25 Apr 2026 13:00:00 +0000

Part 1

Today’s Second Date Update includes probably the MOST AWKWARD 20 minutes of a first date we’ve ever had on this show. And it’s all because of an embarrassing run-in that happened at a bar!

Part 2

If you’re looking for a unique, innovative and new move to pick up women, you need to catch today’s Second Date Update with a guy who swears his tactic worked (at least ONCE).

See omnystudio.com/listener for privacy information.

Second Date Update: Love At First Height

Fri, 24 Apr 2026 15:15:00 +0000

Mike only had one shot to plan a night that Elise would never forget and what happened was definitely memorable… but was it a good memory? Find out in your Second Date Update podcast!

See omnystudio.com/listener for privacy information.

Second Date Update UPDATE: Hot to Huh

Thu, 23 Apr 2026 15:35:00 +0000

We always talk about “the one who got away” but what about “The one who won’t go away?” We’re diving into it when Joe and Sabrina return to our show for a new Second Date Update UPDATE!

See omnystudio.com/listener for privacy information.

Second Date Update: 49er's For Life

Wed, 22 Apr 2026 15:20:00 +0000

There’s a NEW dating term we heard today and whether it’s good or bad, we think it’s gonna catch on SOON to describe a certain type of person… Hear it in your Second Date Update podcast!

See omnystudio.com/listener for privacy information.

Second Date Update: Most Popular Guy In Town

Mon, 20 Apr 2026 15:35:00 +0000

For a minute during her date, our listener on the phone today thought she was out with the most POPULAR guy in town. But is that everything it’s cracked up to be? Find out in your Second Date Update podcast!

See omnystudio.com/listener for privacy information.

Second Date Update Classics: Yup Date For Jessica + 1 Year Later To Rejection King

Sat, 18 Apr 2026 13:00:00 +0000

Part 1

A mysterious handwritten note was dropped onto the table during our listener's date and it altered both of their lives forever!

Part 2

One of our listeners wishes she could take back what she said 11 months ago to a guy she went out with. It took her a year to realize her mistake, and now she wants another chance in a Second Date Update!

See omnystudio.com/listener for privacy information.

Second Date Update Classic: My Wing Mom

Fri, 17 Apr 2026 13:30:00 +0000

The guy on the phone today got an EMERGENCY call on the way to his date, and it put him in a definite lose-lose situation. Tell us what you would have done, once you hear the Second Date Update!

See omnystudio.com/listener for privacy information.

Second Date Update Classic: Hot Date Hijack

Wed, 15 Apr 2026 13:30:00 +0000

What started as a romantic one on one date ended with one of our listeners sandwiched between three gorgeous women all night. He’ll explain how he did it coming up in your Second Date Update!

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Second Date Update: Rez Is Back

Mon, 13 Apr 2026 13:30:00 +0000

What do you do if you’re the ONE PERSON who didn’t get the memo that you’re supposed to bring a gift to the party? One of our listeners had a GENIUS save when that happened to him and it even got him a DATE at the same time!

See omnystudio.com/listener for privacy information.

Second Date Update Classics: The First Five Seconds + Hang Up On Him

Sat, 11 Apr 2026 13:00:00 +0000

Part 1

When you're out to dinner and you notice something on your date's face, do you tell them or keep it to yourself? One of our listeners is worried the choice he made is why he's not getting a call back...

Part 2

One of our listener’s first kiss happened but her second date never did! So we’re gonna do everything in our power to get to the bottom of it in a Second Date Update!

See omnystudio.com/listener for privacy information.

Second Date Update Classic: Show Me The Baby

Fri, 10 Apr 2026 15:01:00 +0000

One of our listeners says it's hard to meet genuine guys who are sensitive to her unique situation, she’ll share what that is in a Second Date podcast!

See omnystudio.com/listener for privacy information.

Second Date Update: Moms Night Out

Wed, 08 Apr 2026 15:05:00 +0000

The woman on the phone today saw something very personal on a guy's book shelf during their first date, and she was so bewildered, she reached out to us as soon as she could!

See omnystudio.com/listener for privacy information.

Second Date Update: Ambushed By Mom

Mon, 06 Apr 2026 15:15:00 +0000

The woman on the phone today tried to take the lead on her date, and her surprise was her own MOTHER. We're not joking, it really happened and you can hear how it went down in your Second Date Update Podcast!

See omnystudio.com/listener for privacy information.

Second Date Update Classics: Secret Mission + Three Wheelin' It

Sat, 04 Apr 2026 13:00:00 +0000

Part 1

One of our listeners was DITCHED on a date in a brazen way, so today we’re on the hunt for ANSWERS.

Part 2

One of our listeners is confused after his date ended in the WEIRDEST way ever… but he still has some interest...

See omnystudio.com/listener for privacy information.

Second Date Update: 15 Minutes Of Lame

Fri, 03 Apr 2026 14:30:00 +0000

Our listener, Jason, has NO IDEA what went wrong on his date with Riley, but SOMETHING must have happened based on how things ended. He asked for our help and we’re ready to dive in, in your Second Date Update podcast!

See omnystudio.com/listener for privacy information.

Second Date Update: Farmers Market Only

Wed, 01 Apr 2026 15:07:00 +0000

One of our listeners purposely arrived OVER AND HOUR AHEAD of their date, and you’ll never believe what they used that time to prepare for. Find out if it backfired or helped in your Second Date Update!

See omnystudio.com/listener for privacy information.

Second Date Update: Dirty Danny the Sexy Shoe Salesman

Mon, 30 Mar 2026 15:30:00 +0000

What’s the boldest move a woman can make on the first date? Our listener on the phone today fears she might have pushed it in her interaction but we’re ready to help her get a Second Date Update!

See omnystudio.com/listener for privacy information.

Second Date Update Classics: Pink Doesn't Stink + Unconventional Beauty and the Feast

Sat, 28 Mar 2026 13:00:00 +0000

Part 1

One of our listeners had women FLOCKING to him thanks to one subtle change to his wardrobe. Hear what it was in your Second Date Update.

Part 2

When a listener describes his date as an "unconventional beauty", we're going to try to uncover if that's the reason she isn't calling him back!

See omnystudio.com/listener for privacy information.

Second Date Update: An Ex Walks Into A Bar

Fri, 27 Mar 2026 15:05:00 +0000

You’re gonna be shocked when you hear how BRIEF the conversation was that brought our listeners date to a COMPLETE and INSTANT STOP. Avoid this sentence if you can, once you hear it, in your Second Date Update podcast!

See omnystudio.com/listener for privacy information.

Second Date Update UPDATE: Marathon Date

Thu, 26 Mar 2026 15:25:00 +0000

One of our listeners ended up on a 10-hour long marathon first date and the only thing more shocking than that... is what happened after we hung up the phone! It’s a Second Date Update UPDATE!

See omnystudio.com/listener for privacy information.

Second Date Update: Dog Parks and Daughters

Wed, 25 Mar 2026 15:47:24 +0000

Our listener wasn’t TRYING to find a romantic connection, it was her 7 year old DAUGHTER who wanted to do it for her. Hear how a sneaky 2nd grader introduced MOMMY to an eligible bachelor in your Second Date Update podcast!

See omnystudio.com/listener for privacy information.

Second Date Update: Sunset Scribbles

Mon, 23 Mar 2026 15:20:00 +0000

The woman on the phone today says not only was her date a “solid 9” but the date he planned for them put him head and shoulders above the rest! So why isn’t he calling her back? Find out in the Second Date Update podcast!

See omnystudio.com/listener for privacy information.

Second Date Update Classics: Ride of Shame + Incriminating News at 11

Sat, 21 Mar 2026 13:00:00 +0000

Part 1

How can you parlay one night of fun with a person you met at the club into something more meaningful? We're going to help one of our listeners try to do exactly that.

Part 2

One of our listeners got their 15 seconds of fame DURING A DATE and it included tv cameras recording EVERYTHING he said…

See omnystudio.com/listener for privacy information.

Second Date Update: The Best Listener Ever

Fri, 20 Mar 2026 14:25:00 +0000

James came on our show a few months ago and actually USED his previous experience to change for the better?? Hear how he’s worked to become a better DATER in your Second Date Update podcast!

See omnystudio.com/listener for privacy information.

Second Date Update: A Whole New Girlfriend

Wed, 18 Mar 2026 15:30:00 +0000

One of our listeners REGRETS being honest about his favorite hobby… he knows it can be a red flag for some women and he’s hoping we can help smooth it over in your Second Date Update podcast!

See omnystudio.com/listener for privacy information.

Second Date Update: Ghost Date Hijack

Mon, 16 Mar 2026 15:05:00 +0000

Our listener says his date got totally derailed by an anonymous stranger and if he doesn’t find out WHO the veiled figure is, he may never get another shot to take Mysty to dinner!

See omnystudio.com/listener for privacy information.

Second Date Update Classics: A Picture Says A Thousand Icks + Appetizer Energy, Entrée Problems

Sat, 14 Mar 2026 13:00:00 +0000

Part 1

The guy on the phone today claims his date said one specific thing to their waiter that wasn't just a green flag...but made him instantly realize she was relationship material!

Part 2

One of our listeners THOUGHT he had a second chance all lined up with his date, but a single one-word text message brought that reality crashing down.

See omnystudio.com/listener for privacy information.

Second Date Update: Champagne and Shackles

Fri, 13 Mar 2026 13:30:00 +0000

One of our listeners ended up in the bathroom alongside her date and NOT in a good way… You’ll hear why she had no choice but to bring him with her in a Second Date Update!

See omnystudio.com/listener for privacy information.

Second Date Update: High Steaks Heartbreak

Wed, 11 Mar 2026 15:10:00 +0000

One of our listeners found the ULTIMATE HACK to take a woman out, without breaking the bank. It requires a tad bit of deception though… find out more in your Second Date Update podcast!

See omnystudio.com/listener for privacy information.

Second Date Update Classics: The Rudy of Dating + Date Night Veto

Sat, 07 Mar 2026 14:00:00 +0000

Part 1

The guy on the phone for today’s Second Date Update says we need to get him ANSWERS, not just for his sanity, but for his FRIEND GROUP who played a strange role in his date.

Part 2

One of our female listeners used an innocent little excuse…. To go from awkward end of the night hug… to Instant sleepover at his place… Your gonna hear how she did it!

See omnystudio.com/listener for privacy information.

Second Date Update: Taking The Plunge

Fri, 06 Mar 2026 16:05:00 +0000

One of our listeners was MORTIFIED when her date accidentally saw something that was NEVER intended for his eyes… She needs our help with a Second Date Update!

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Second Date Update UPDATE: Gucci First Questions Later

Thu, 05 Mar 2026 16:05:00 +0000

Is it better to find true love or a rich guy with a big boat? Today we’ll finally learn the answer in a special Second Date Update UPDATE!

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Second Date Update: Late Night Lab Experiment

Wed, 04 Mar 2026 16:05:00 +0000

One of our listeners says she found the EXACT right time to strike up a conversation with the cutest guy in the room… Find out how the shy science girl got the courage to do it, in your Second Date Update podcast!

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Second Date Update: Pawn Shop Shopping Trip

Mon, 02 Mar 2026 16:30:00 +0000

The listener on the phone today TRIED to buy a woman a gift in the middle of their date, but he never actually GOT it and the reason WHY is actually pretty hilarious. It's your Second Date Update Podcast!

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Second Date Update Classics: Right To Remain Sexy + Scooter Safety Patrol

Sat, 28 Feb 2026 14:00:00 +0000

Part 1

One of our listeners says HIS DATE asked him to do something UNUSUAL shortly after they sat down, and he thinks it's part of why he’s not getting a call back.

Part 2

The guy on the phone today had a run-in with a woman who wouldn’t stop SCREAMING at him during his first date. You’re not gonna believe the topic that set her off!

See omnystudio.com/listener for privacy information.

Second Date Update: Two Year Ghost Job

Fri, 27 Feb 2026 16:15:00 +0000

The woman on the phone admits what she did to her date was LOWER than LOW. Now, two years later, she’s finally ready to make it right, in a Second Date Update!

See omnystudio.com/listener for privacy information.

Second Date Update: So Turned On

Wed, 25 Feb 2026 16:30:00 +0000

One of our listeners thinks that playing with his FOOD is part of the reason why he isn’t getting a call back… Only way to know for sure is to have him on for a Second Date Update!

See omnystudio.com/listener for privacy information.

Second Date Update: Bros Before Kim

Mon, 23 Feb 2026 16:05:00 +0000

One of our listeners says he was given no choice but to LIE right to his date’s face… Cuz if he was Truthful about why he REALLY had to suddenly leave... she’d probably never talk to him again.

See omnystudio.com/listener for privacy information.

Second Date Update Classics: Ex Marks The Shot + Better Late Than Never

Sat, 21 Feb 2026 14:00:00 +0000

Part 1

We were shocked when we heard about our listeners tense situation that went down on a first date with an UNEXPECTED VISITOR…

Part 2

Something happened to our listener on his way to the first meetup with his date, and it changed the trajectory of their entire night!

See omnystudio.com/listener for privacy information.

Second Date Update Classic: Saved By The Shrimp

Fri, 20 Feb 2026 14:30:00 +0000

The guy in today’s Second Date had to do something DRASTIC in order to save his date from going off the rails. Find out what it was in the podcast!

See omnystudio.com/listener for privacy information.

Second Date Update Classic: Double Kiss Surprise

Wed, 18 Feb 2026 14:30:00 +0000

One of our listeners was trying to walk a thin line in trying to get a man to notice her, and pulled a move that maybe went a little too far…

See omnystudio.com/listener for privacy information.

Second Date Update Classic: Motel 7

Tue, 17 Feb 2026 02:30:00 +0000

The guy in today’s Second Date had ONE SHOT and ONE NIGHT with a woman while she was in town… and he admits… some weird stuff happened.

See omnystudio.com/listener for privacy information.

Second Date Update Classics: Scam the Scammer + V-Day Pass Out

Sat, 14 Feb 2026 14:00:00 +0000

Part 1

One of our listeners is FURIOUS after her date left her in the most embarrassing situation of her life… and now she wants not just answers, but REVENGE.

Part 2

One of our listeners ended up in the HOSPITAL right in the middle of his first date… and he can’t believe he was naïve enough to make this dumb, avoidable choice… You’ll hear it in a special Valentine’s Day Second Date Update!

See omnystudio.com/listener for privacy information.

Second Date Update Classic: Valentine's Day Fork

Fri, 13 Feb 2026 16:05:00 +0000

Cupid needs our help with a Valentine’s Day emergency! The woman on the phone says they were KICKED OUT of a restaurant on their date but she insists it was one of the best meetups she’s ever had.

See omnystudio.com/listener for privacy information.

Second Date Update UPDATE: Family Dinner Drama

Thu, 12 Feb 2026 17:10:00 +0000

Gillian and Thomas were on our show a few months ago after some drama happened on their date over a family recipe. Now, they’re BACK for a special Second Date Update UPDATE!

See omnystudio.com/listener for privacy information.

Second Date Update: Universe Is Busy

Wed, 11 Feb 2026 16:10:00 +0000

One of our listeners SWEARS she found the fool-proof method to turn your dream guy into a reality! She’ll explain how she manifested him in your Second Date Update podcast!

See omnystudio.com/listener for privacy information.

Second Date Update: Hired A Hinge Coach

Mon, 09 Feb 2026 16:10:00 +0000

The guy on the phone today hired a PRO dating coach, and says he learned one line that worked INSTANTLY to attract a quality woman. You can STEAL it once you find out what it is in your Second Date Update!

See omnystudio.com/listener for privacy information.

Second Date Update Classics: Car Talk + I Woke Up Where?

Sat, 07 Feb 2026 13:30:00 +0000

Part 1

The woman on the phone today got an INTERESTING surprise when she got into her date's car, and that kind of weirdness is something we can all get behind on this show!

Part 2

One of our listeners needs our help piecing together his night because he woke up not in his bed, not in her bed, and not even in a bed at all!

See omnystudio.com/listener for privacy information.

Second Date Update: Unattractive Trey Is Back

Fri, 06 Feb 2026 16:35:00 +0000

One of our listeners did something HEROIC for a stranger, and it got him a date! Meet our hero in today's Second Date Update!

See omnystudio.com/listener for privacy information.

Second Date Update: My Ears Are Clogged With Love

Wed, 04 Feb 2026 16:25:00 +0000

The woman on the phone today was taken on one of the LEAST romantic dates we’ve ever heard of, and she says she CAN’T STOP thinking about the guy! We’ll try to track him down in a Second Date Update!

See omnystudio.com/listener for privacy information.

Second Date Update: No Snow Show

Mon, 02 Feb 2026 16:15:00 +0000

The woman on the phone today learned the HARD WAY after her date promised to give her a luxurious “experience of a lifetime” that she shouldn’t be so quick to trust. She’s ready to call him out in a Second Date Update!

See omnystudio.com/listener for privacy information.

Second Date Update Classics: Sweet Sixteen Dates+ Be Excellent & Be Thirsty

Sat, 31 Jan 2026 14:00:00 +0000

Part 1

There’s a brand new food item that you should definitely AVOID ordering on a first date unless you want to end up like one of our listeners. We’ll hear what it was and try to help him recover in your Second Date Update.

Part 2

One of our listeners had not one but TWO opportunities to be a “Knight In Shining Armor” for his date… so why is she ignoring him after his heroism? Time to find out!

See omnystudio.com/listener for privacy information.

Second Date Update: Bending and Unfriending

Fri, 30 Jan 2026 16:25:00 +0000

The guy on the phone today put on a special THEMED DATE for his online match, and it lasted a whole fifteen minutes… Hear what sent her running in your Second Date Update!

See omnystudio.com/listener for privacy information.

Second Date Update: Corn Dog

Wed, 28 Jan 2026 16:10:00 +0000

The guy on the phone today asked out someone that he works with and we DID NOT expect to hear what happened after that! Find out what it is in your Second Date Update podcast!

See omnystudio.com/listener for privacy information.

Second Date Update: Bachelor Party of One

Mon, 26 Jan 2026 16:15:00 +0000

This may be the BIGGEST RED FLAG we’ve ever heard on a first date… yet somehow, they still hooked up afterwords??

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Second Date Update Classics: Beauty and the Meh + Getaway Car

Sat, 24 Jan 2026 14:00:00 +0000

Part 1

The guy on the phone today says he managed to pull a woman WAY out of his league, and it's all thanks to ONE move he pulled at the very end of the date!

Part 2

One of our listeners says he doesn’t need help getting a hold of the woman he dated… he needs our help to avoid criminal prosecution instead!

See omnystudio.com/listener for privacy information.

Second Date Update: Sneeze Sympatico

Fri, 23 Jan 2026 16:15:00 +0000

One of our listeners unintentionally did something at the EXACT SAME TIME as his date, and he says it’s a sign of something HUGE! Hear what it is coming up in your Second Date Update podcast!

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Second Date Update: First Timers Club

Wed, 21 Jan 2026 16:25:00 +0000

The guy on the phone today is a member of the “first timers club.” What’s the first timers club, exactly? Find out for yourself when we do a Second Date Update!

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Second Date Update Classic: Pet Store Probation

Tue, 20 Jan 2026 02:30:00 +0000

One of our listeners has a unique technique in order to give herself a pick-me-up on a date. And not only did it work for her, it led her to a guy she really likes too! Hear her strategy in your Second Date Update!

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Second Date Update Classics: Pop Some Tags + Love At First Flight

Sat, 17 Jan 2026 14:00:00 +0000

Part 1

A little drawing on a cocktail napkin didn’t go the way our listener planned, and neither did his date night! You’ll understand why in the Second Date Update.

Part 2

Just when you thought nothing good happens on airplanes anymore, one of our listeners met a woman on a flight and his story might inspire everyone listening!

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Second Date Update: Leave Wicky Alone

Fri, 16 Jan 2026 16:15:00 +0000

The guy on the phone today got caught showing up to his date after getting dropped off by ANOTHER WOMAN! We’re readying our battle stations for a contentious Second Date Update!

See omnystudio.com/listener for privacy information.

Second Date Update UPDATE: Pre-Block

Thu, 15 Jan 2026 16:15:00 +0000

One of our listeners asked his date a question that was RUDE, INSENSITIVE, and INAPPROPRIATE… at least we thought at first… Now he’s back for a special Second Date Update UPDATE!

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Second Date Update: Mom Plus One

Wed, 14 Jan 2026 16:15:00 +0000

Ethan started his night meeting one woman, and ended up with a completely different one at his table by the end of the night! He’s desperate for a Second Date Update and we’re gonna give him one!

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Second Date Update: Dry Lips & Hands On Hips

Mon, 12 Jan 2026 16:35:00 +0000

All the guy on the phone today had to do to make himself PERFECT for his date is change TWO PHYSICAL things about himself… It backfired and now he wants a Second Date Update!

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Second Date Update Classics: Cobra Bye + Taco Truckstop Mystery

Sat, 10 Jan 2026 13:30:00 +0000

Part 1

One of our listeners didn’t admit her guilty pleasure to her date, she THEMED their entire evening around it. Now she’s not getting a call back?

Part 2

One of the most popular Second Date Updates from last year is BACK… the bad news is the guy she went out with is trying to avoid her (he even RAN AWAY). We’re gonna try to find out why in the podcast!

See omnystudio.com/listener for privacy information.

Second Date Update: Bathroom 911

Fri, 09 Jan 2026 16:15:00 +0000

The guy on the phone today is willing to tell us the MOST EMBARRASSING date night of his life… in hopes it will get him another shot with the woman he loves. Will it be worth the humiliation? Find out in the Second Date Update!

See omnystudio.com/listener for privacy information.

Second Date Update Classic: Eyes Closed Mouth Open

Wed, 07 Jan 2026 15:15:00 +0000

There’s one moment in every date where you can end on a high note, or push your luck and risk it all. One of our listeners says he definitely made the WRONG choice on his date and now he’s on the line looking for help with a Second Date Update.

See omnystudio.com/listener for privacy information.

Second Date Update Classic: High Stakes Higher Stacks

Mon, 05 Jan 2026 16:30:00 +0000

There’s one thing a guy can put on his dating profile that will instantly up his chances of matching by 90%... The woman on the phone today saw it on her date's profile and now she wants our help locking him down in a Second Date Update!

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Second Date Update Classics: 401 Not Ok + Offline and Oblivious

Sat, 03 Jan 2026 13:30:00 +0000

Part 1

One of our listeners said she added 3 little numbers to her dating profile and it made her matches go through the roof! Find out what it was in the podcast!

Part 2

The guy in today’s Second Date Update DID NOT google his date before meeting up with her and sure wishes he did now! Good thing she'll reveal her juicy secret to us.

See omnystudio.com/listener for privacy information.

Second Date Update Classics: High School Holiday Hangout + Trial By Separation

Sat, 27 Dec 2025 13:30:00 +0000

Part 1

One of our listeners thought inviting a guy over might save her from spending time with her parents while home for the holidays… but we're going to hear how badly it backfired.

Part 2

The guy in today’s Second Date has been off the market for a decade and after his first date back in the game he’s getting left on read!

See omnystudio.com/listener for privacy information.

Second Date Update Classics: The Boy Who Cried Tree + Deck The Mall

Sat, 20 Dec 2025 13:30:00 +0000

Part 1

After we totally botched a Second Date for a guy a few months ago, he’s back and at this point we’re not sure if he’s trolling us or just likes the punishment. We can't let him down this time!

Part 2

Imagine if you went on a date with a coworker and after the hang out, MULTIPLE PEOPLE are now avoiding you. It happened to one of our listeners and you can hear why in a Second Date!

See omnystudio.com/listener for privacy information.

Second Date Update Classics: 3rd Times a Yawn + Super Kid Shames the Day

Sat, 13 Dec 2025 13:30:00 +0000

Part 1

The guy on the phone today told us he’s fed up with being friend-zoned, and he wants to get ahead of things with a bizarre new plan we’ve never tried before!

Part 2

The guy on the phone says a random child walked up to their table during a romantic dinner and said something that threw off their ENTIRE EVENING. Is a kid really to blame for him not getting a Second Date?

See omnystudio.com/listener for privacy information.

Second Date Update: He Bought Me A Star

Mon, 08 Dec 2025 16:40:00 +0000

It can be so difficult to find a guy who does the bare minimum, but the woman on the phone today found a guy who is OUT OF THIS WORLD! We’ll let her explain why she wants to see her date again, in your Second Date Update podcast!

See omnystudio.com/listener for privacy information.

Second Date Update Classics: Double Roasted Turkey + 20 Treadmills of Love

Sat, 06 Dec 2025 13:30:00 +0000

Part 1

One of our listeners met a guy in a peculiar way… by SAVING HIS LIFE! But why doesn’t he ever want to see her again? We’ll use a Second Date Update to find out.

Part 2

The woman on the phone today was SHOCKED when she got a look inside her date's home and saw what he collects...Even though he swears it's for a good reason. Find out what it is in the podcast!

See omnystudio.com/listener for privacy information.

Second Date Update: Never Ask About The Ex

Fri, 05 Dec 2025 16:20:00 +0000

The guy on the phone today has HUGE regrets about asking his date about Ex...Yet he still wants our help getting in touch with her for a Second Date Update!

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Second Date Update UPDATE: Age Is Just A Bummer

Thu, 04 Dec 2025 16:15:00 +0000

The couple on the phone today got the most AWKWARD comment a server could say to a table when they first appeared on our show a few months ago. Now, they’re BACK to give us a special Second Date Update UPDATE!

See omnystudio.com/listener for privacy information.

Second Date Update: Beer & Butterfly Kisses

Wed, 03 Dec 2025 16:15:00 +0000

The woman on the phone today is CERTAIN that there is a logical explanation for why her date suddenly dropped off the face of the earth after ten days… We’re gonna help her KEEP HOPE ALIVE in your Second Date Update podcast!

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Second Date Update: Love Bombs Away

Mon, 01 Dec 2025 16:35:00 +0000

One of our listeners wanted to sweep his date off her feet….. but based on the reactions we got in this room to his grand romantic gestures there’s a chance he MAY have overdone it… See for yourself in the Second Date Update podcast!

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Second Date Update Classics: Driving Miss Laurie + Lick My Neck

Sat, 29 Nov 2025 13:30:00 +0000

Part 1

One of our listeners said he changed ONE THING on his dating profile that instantly changed the game for him. He wishes he’d done this years ago and you can hear what it is in the Second Date podcast.

Part 2

Out of every Second Date we’ve done this year, today's might be the most MEMORABLE of the bunch.

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Second Date Update Classic: Cutecumber Couple

Fri, 28 Nov 2025 14:30:00 +0000

One of our listeners says he got his inspiration for his dating “MOVE” by watching on video online and gathering the courage to try it himself. Hear what it was in a Second Date podcast!

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Second Date Update UPDATE Classic: 8 Trees A Trimming

Thu, 27 Nov 2025 14:30:00 +0000

The holidays nearly broke up the couple on the phone today when they first dated a year ago. But now with the yuletide season coming up were going to reconnect with them for a special update!

See omnystudio.com/listener for privacy information.

Second Date Update Classic: First Date Redate

Wed, 26 Nov 2025 14:30:00 +0000

The guy in today’s Second Date Update has been on the show before, but today he gets the special opportunity for a First Date REDATE!

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Second Date Update Classic: Red Flaggy Much?

Mon, 24 Nov 2025 14:30:00 +0000

One of our listeners said he made a restaurant faux pas RIGHT AWAY on his date before he even put down the menu. We’ll talk to him and see if it derailed his chances in your Second Date Update!

See omnystudio.com/listener for privacy information.

Second Date Update Classics: Date Night Detour + Barista Foam Job

Sat, 22 Nov 2025 13:30:00 +0000

Part 1

If you asked a million people if they thought the surprise one of our listeners had for the woman he was dating was a good idea, NOBODY would say “YES!”

Part 2

One of our listeners is a barista and says she did something she would NEVER normally do… but taking that risk got her a date with a hot customer and now she wants our assistance bringing him back one more time!

See omnystudio.com/listener for privacy information.

Second Date Update: Microwave Mosaics

Fri, 21 Nov 2025 16:20:00 +0000

Kevin’s unique hobby might be one of the weirdest things we’ve heard and we’re wondering if MAYBE it's reason he isn’t getting a call back...But it's also what makes him one of the most memorable listeners we've ever had on the show!

See omnystudio.com/listener for privacy information.

Second Date Update: Escalator Escape

Wed, 19 Nov 2025 16:10:00 +0000

The woman on the phone today says she was FORCED to confront her biggest fear in the first 5 minutes of her date. We’ll figure out what she’s so scared of in your Second Date Update podcast!

See omnystudio.com/listener for privacy information.

Second Date Update: Bottom of the Bread Bowl

Mon, 17 Nov 2025 16:50:00 +0000

One of our listeners tried a dating HACK in today’s Second Date Update that guys might find useful, women probably hate it, and we’re just surprised it was even a THING!

See omnystudio.com/listener for privacy information.

Second Date Update Classics: Strings of Deceit + Claus for Concern

Sat, 15 Nov 2025 13:35:00 +0000

Part 1

Sometimes just one photo can raise the reddest of red flags and that happened to one of our listeners. She noticed something on a guys profile pic and now she wants our help finding him and getting him to explain.

Part 2

One of our listeners swears he has a very good reason that’s totally “not sketch at all” for wanting to make sure his date location was EXTRA PRIVATE… We’re gonna hear him out in your Second Date Update.

See omnystudio.com/listener for privacy information.

Second Date Update: Awkward Hugs & Hot Dogs

Fri, 14 Nov 2025 16:12:01 +0000

The guy on the phone today says he left his date alone in his apartment and when he came back she was ready to BOLT away. We’re gonna try to figure out what spooked her in your Second Date Update podcast!

See omnystudio.com/listener for privacy information.

Second Date Update: Ditch Me No Ditch You

Mon, 10 Nov 2025 16:17:04 +0000

We have a CONTROVERSIAL Second Date Update today where at some point during the date, somebody DEMANDED to speak to the restaurant manager. We’re in crisis mode in the podcast!

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Second Date Update Classics: Seafood Surprise + Philippines or Bust

Sat, 08 Nov 2025 14:00:00 +0000

Part 1

The guy on the phone today says his date night included a blindfold and a bit of deception, but it turned out even better than he ever planned. Hear what happened in your Second Date podcast.

Part 2

The guy in today’s Second Date Update flew across the ocean just to meet someone he thinks MIGHT be the ONE!

See omnystudio.com/listener for privacy information.

Second Date Update: Karaoke Cryer

Fri, 07 Nov 2025 16:17:14 +0000

Something was EXPELLED from the body of one of our listeners while on a date, and while it wasn’t gross, it did happen for over an hour....But it’s not dissuading our listener from trying to get a Second Date!

See omnystudio.com/listener for privacy information.

Second Date Update: 30 for 30

Wed, 05 Nov 2025 16:42:07 +0000

One of our listeners is experimenting in a new dating strategy, all about the YEAR she was born. Find out what she’s doing in your Second Date Update podcast!

See omnystudio.com/listener for privacy information.

Second Date Update: Red Flag Test

Mon, 03 Nov 2025 16:16:56 +0000

We needed the listener on the phone today to be 100% HONEST about what happened with his date, and that proved to be harder than we realized…

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Second Date Update Classics: It's A Costume Dummy + Blackout Drunk Shuttlecock

Sat, 01 Nov 2025 12:30:00 +0000

Part 1

The guy in today’s Second Date Update tried a pickup line that was cringey, not just on one level… but on MULTIPLE LEVELS and he quickly realized he needed our help.

Part 2

One of our listeners found themselves in the middle of an epic house party and he thinks he found a girl he wants to get serious with… but something happened on the way over to the daiquiri mix… and we’re about to get to the bottom of it in your Second Date Update!

See omnystudio.com/listener for privacy information.

Second Date Update: Halloween Boos and Booze Bar Crawl

Fri, 31 Oct 2025 15:37:16 +0000

One critical moment told the ENTIRE story of our listener's date and now they BOTH can’t stop talking about it. Hear how it went down in your Halloween Second Date Update podcast!

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Second Date Update: Halloween Bean Dip Mystery

Wed, 29 Oct 2025 15:12:07 +0000

A family member showed up out of NOWHERE on our listeners date, and what happened next made everyone’s skin crawl. Catch it all in your Second Date Update podcast!

See omnystudio.com/listener for privacy information.