Today

Second Date Update: Float & Boat

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!See omnystudio.com/listener for privacy information.

19m 39s

Yesterday

Awkward Tuesday: Haunting of Boyfriends Past

Today’s Halloween Edition of the Awkward Tuesday Phone Call is a mortifying conversation between two people who REALLY don’t like each other anymore!See omnystudio.com/listener for privacy information.

19m 7s

Oct 26

Second Date Update: Haunted House Hero

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!See omnystudio.com/listener for privacy information.

17m 53s

Jul 2025

Second Date Update: Randall Is Back For More

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 in your bran ... Show More

16m 54s

Feb 2025

Second Date Update UPDATE: We Built This Thing Together

Not everyone is wired to be ultra-romantic… that was an issue for one of our listeners months ago when they were on our show. Today he’s back and we’ll see if anything has changed since then in a Second Date Update UPDATE!See omnystudio.com/listener for privacy information.

16m 23s

Mar 2025

Second Date Update: First Date Redate

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!See omnystudio.com/listener for privacy information.

16m 48s

Jun 2025

Second Date Update: 1st Impressions Are Everything

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. Hear what she went through in a new Second Date Update!See omnystudio.com/listener for privacy information.

17m 50s

Mar 2025

Second Date Update: Taco Truckstop Mystery

<p>A listener from one of the most popular Second Date Updates of 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!</p><p>See <a href="https://omnystudio.com/listene ... Show More

17m 14s

Mar 2025

Second Date Update Classic: Hot Date Hijack

What started as a romantic one on one date ended with our listener sandwiched between three gorgeous women all night! He’ll explain how he did it coming up in your Second Date Update podcast! Get your 2nd Date Update Merch For A Cause HERE!See omnystudio.com/listener for privacy ... Show More

16m 1s

Jul 2025

Second Date Update Classics: Recreate the Scene + Lifetimes of Love

Part 1One of our listeners decided his goal was to bring the magic of RomComs to his dating life...Now we need to help him finish his love story!Part 2The guy on the phone says one text before the date started changed their ENTIRE NIGHT—Find out what it was in your Second Date Up ... Show More

36m 24s

Jul 2025

Second Date Update: One More Refill

A request made at a dinner date might have crossed the line… but the listener on the phone says he was well within his rights on his date! Hear how it went down in a brand new Second Date Update.See omnystudio.com/listener for privacy information.

17m 43s

May 2025

Second Date Update: Three Wheelin' It

One of our listeners is confused after his date ended in the WEIRDEST way ever… but he still has SOME interest. Hear the brand new Second Date Update in the podcast! Get your 2nd Date Update Merch For A Cause HERE!See omnystudio.com/listener for privacy information.

17m 22s

Aug 2025

Second Date Update: Marathon Date

One of our listeners said his date was a 10/10 and going flawlessly, that's why he couldn't believe what happened when he went in for the first kiss...We're gonna hear it in a brand new Second Date Update. See omnystudio.com/listener for privacy information.

17m 7s

Second Date Update: Randall Is Back For ...