Today

Second Date Update: A Slip of the Ex

One of our listeners claims they’ve discovered the GOLDEN pick-up line, hear what it is in a brand new Second Date Update podcast!See omnystudio.com/listener for privacy information.

17m 46s

Yesterday

Awkward Tuesday: Kids Party Problem

After something went awry at a kid’s birthday party ONE YEAR AGO something is STILL causing a rift… and we’re being asked to settle it with a brand new Awkward Tuesday Phone Call!See omnystudio.com/listener for privacy information.

19m 15s

Jul 7

Second Date Update: Vacation No No

One of our listeners planned a first date to last 5 full days with a woman he had never even met before! We’ll hear what happened in your Second Date Update podcast!See omnystudio.com/listener for privacy information.

17m 4s

Jun 24

Awkward Tuesday: Prenup or Pre-NOPE

One of our listeners has a looming conversation coming up and it’s one of the most difficult things you could ever talk about with a loved one. Before it happens they want our help via an Awkward Tuesday Phone Call!See omnystudio.com/listener for privacy information.

17m 30s

Oct 2015

PODCAST: Awkward Tuesday Phone Call – Impure Thoughts

Today, one of our listeners wants to come clean to his girlfriend about something naughty he did, that HE SAYS violated his girlfriend's trust... We think he probably overreacting. But he's determined to confess. All we can do is TRY and support him in his Awkward Tuesday Phone C ... Show More

14m 41s

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 15

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

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

Oct 2024

Second Date Update Classic: Love Me A Lengthy Lady

The guy on the phone today was asked an important question during his date, and in a moment of panic he thinks he may have given the most awkward response possible! Hear the Second Date podcast right here!See omnystudio.com/listener for privacy information.

16m 22s

Jun 20

Second Date Update: Brunch Yuck

One of our listeners DEFINITELY regrets a story he told on his date, and you’re gonna want to hear how he tells it in the Second Date Update podcast!See omnystudio.com/listener for privacy information.

17m 29s

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 Chumbs

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

Awkward Tuesday: I Don't Love My Boss