Podcast Episodes

Awkward Tuesday: Stop That Ugly Duckling

Is it ever okay for a person to meddle in their friends love life? It doesn’t matter because we’re doing it anyway before one listener's friend can go on a blind date!

See omnystudio.com/listener for …

Published on 1 month ago

Second Date Update Classic: Red Flaggy Much?

One of our listeners said he made a restaurant faux pas RIGHT AWAY on his date before he even put down the menu. We’ll talk to him and see if it derailed his chances in your Second Date Update!

See om…

Published on 1 month ago

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 feed, Brooke & Jeffrey! We'd love to hear your feedb…

Published on 1 month 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 say “YES!”

Part 2

One of our listeners is a baris…

Published on 1 month 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 also what makes him one of the most memorable lis…

Published on 1 month 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.

Published on 1 month 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 scared of in your Second Date Update podcast!

See omnys…

Published on 1 month, 1 week 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 get down to the nitty gritty, in the podcast!

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Published on 1 month, 1 week 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 it was even a THING!

See omnystudio.com/listener fo…

Published on 1 month, 1 week 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 feed, Brooke & Jeffrey! We'd love to hear your feedb…

Published on 1 month, 1 week ago