Yesterday

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

Jul 8

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

Jan 2025

Awkward Tuesday: Carrot Top Jackpot

One of our listeners is about to get fantastic news… His wife went on a girls trip to Vegas and maybe one of the best things ever just happened to her… in your Awkward Tuesday Phone Call!See omnystudio.com/listener for privacy information.

16m 17s

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

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

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: 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

Apr 8

Awkward Tuesday: Bonjour Betrayal

One of our listeners has a dilemma. Her friend asked her to tell the biggest lie of her life, or it might cost someone their career! We’ll help her through it in a brand new Awkward Tuesday Phone Call!See omnystudio.com/listener for privacy information.

15m 51s

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

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 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

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

Awkward Tuesday: There's Something About...