Podcast Episodes

FULL SHOW: Jeff’s Iconic Thanksgiving Song, Turkey Day Mishaps + Late & Petty Date (11/21/25)

We're trying out a new idea for our fans of the 2nd Date Update! Every Sunday, we will be hosting one of our FULL HOUR episodes from our main show fe…

4 months, 1 week ago

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…

4 months, 1 week ago

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…

4 months, 2 weeks ago

Top 10 Loser Lines of 2025

We're counting down our TEN FAVORITE Loser Line Clips of the entire year!

See omnystudio.com/listener for privacy information.

4 months, 2 weeks ago

Second Date Update: Escalator Escape

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 scar…

4 months, 2 weeks ago

Awkward Tuesday: Wanna Be A Cop

In your Awkward Tuesday Phone Call, one of our listeners think his girlfriend’s new career path might be putting her in DANGER! We’ll sort it out and…

4 months, 2 weeks ago

Second Date Update: Bottom of the Bread Bowl

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 …

4 months, 2 weeks ago

FULL SHOW: The Only Match Date, Jeff’s Celebrity Man Crush + Jose’s $100 Soup (11/12/25)

We're trying out a new idea for our fans of the 2nd Date Update! Every Sunday, we will be hosting one of our FULL HOUR episodes from our main show fe…

4 months, 2 weeks ago

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

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…

4 months, 2 weeks ago

Second Date Update: Awkward Hugs & Hot Dogs

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 o…

4 months, 3 weeks ago