Yesterday

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

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 ... Show More

37 m

Nov 21

Second Date Update: Microwave Mosaics

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 <a href=" ... Show More

19m 22s

Nov 20

Top 10 Loser Lines of 2025

We're counting down our TEN FAVORITE Loser Line Clips of the entire year!See <a href="https://omnystudio.com/listener">omnystudio.com/listener</a> for privacy information.

18m 15s

Jan 2025

Second Date Update: Standup Standoff

We had a problem with today’s Second Date Update that we’ve NEVER experienced before and it probably says a lot about why one of our listeners is asking us for dating help.See omnystudio.com/listener for privacy information.

17m 1s

Feb 2025

Second Date Update Classic: Offer He Can't Refuse

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. Second Date Update podcast is right here for ya!See omnystudio.com/listener for privacy information.

15m 28s

Apr 2025

Awkward Tuesday: 15 Minutes of Gurt

How do you tell someone you love that their wildest dream might not be achievable? One of our listeners has that very problem with her boyfriend and she chose to email us for an Awkward Tuesday Phone Call!See omnystudio.com/listener for privacy information.

16m 17s

Oct 21

Awkward Tuesday: Tinder Surprise

One of our listeners asked us for help with an Awkward Tuesday Phone Call but ended up BLINDSIDING us and his girlfriend at the same time. You gotta hear it in the podcast!See omnystudio.com/listener for privacy information.

17m 24s

Oct 25

Second Date Update Classics: 10 Pin Mixup + Pop Goes the Relationship

Part 1How badly are you willing to embarrass yourself if it means getting a date with that special person? One of our listeners went to the limit LIVE ON AIR and you get to hear it!Part 2A listener on the phone today says his first kiss with his date left a LOT to be desired… and ... Show More

36m 4s

Jan 2025

Second Date Update: 5-Second Holiday Makeout Hack

One of our listeners took a weird piece of romantic advice and was SHOCKED when it worked! He says it could work for anyone, and we’ll talk to him in the Second Date Update podcast!See omnystudio.com/listener for privacy information.

17m 1s

Mar 2025

Second Date Update: Phone Paux

One of our listeners became best friends with a fellow gym-goer before he decided to ask her on a date… You’ll hear how he did it in your Second Date Update podcast! Get your 2nd Date Update Merch For A Cause HERE!See omnystudio.com/listener for privacy information.

17m 51s

Mar 2025

Second Date Update: Dragon Thumbs and Aroma Chums

One of our listeners made her date laugh so hard that something embarrassing slipped out and she’s worried it’s the reason he’s not calling back!See omnystudio.com/listener for privacy information.

17m 35s

Oct 2024

Awkward Tuesday: Bullied By My Exes Kid

One of our listeners had her daughter come home in tears and she says the only way to fix it is if we helped her a brand new Awkward Tuesday Phone Call!See omnystudio.com/listener for privacy information.

15m 39s

Sep 2024

Second Date Update: Old Flame New Burn

There’s some topics you just don’t bring up on a first date. One of our listeners didn’t follow that rule and now it’s no surprise he needs our help in a brand new Second Date podcast!See omnystudio.com/listener for privacy information.

16m 27s

Awkward Tuesday: I Don't Love My Boss