Podcast Episodes

Closure Call: Sister Secret

One of our listeners had a drunken night at the bar and it led to an entire year of silence between her and her sister. Now she wants our help reuniting the family with a Closure Call!

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Published on 8 hours ago

#5 Second Date Update of 2025: 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 pr…

Published on 1 day, 8 hours ago

Awkward Tuesday Classic: Invisible Girlfriend

In your Awkward Tuesday Phone Call, one of our listeners is convinced her brother is hiding a big secret from the family, and she wants to reveal it with our help!

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Published on 2 days, 8 hours ago

#6 Second Date Update of 2025: Lonely Cannoli

A quick trip to move his car ended up being a HUGE mistake for our listener, and it sent his date WILDLY OFF TRACK. Hear how it went down in a Second Date Update!

See omnystudio.com/listener for priva…

Published on 3 days, 8 hours ago

FULL SHOW: Dating App Hack Date, Brooke vs Christmas Dads + Jeff’s Back Alley Boat (12/17/25)

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 4 days, 9 hours ago

Second Date Update Classics: The Boy Who Cried Tree + Deck The Mall

Part 1

After we totally botched a Second Date for a guy a few months ago, he’s back and at this point we’re not sure if he’s trolling us or just likes the punishment. We can't let him down this time!…

Published on 5 days, 9 hours ago

#7 Second Date Update of 2025: Street Walker Love Story

One of our listeners turned a super awkward moment into an actual MEET CUTE that almost seemed TOO perfect. You’ll hear it in your Second Date Update podcast!

See omnystudio.com/listener for privacy i…

Published on 6 days, 8 hours ago

Brooke Breaks You Up: Holiday Edition

It’s one of the most controversial segments in the history of our show, but today it comes with a twist. It's the Holiday Edition of Brooke Breaks You Up!

See omnystudio.com/listener for privacy infor…

Published on 1 week ago

#8 Second Date Update of 2025: That Name Sounds Familiar

The most annoying part of dating apps is all the wasted energy you put in, only to never actually meet up in person… But our listener on the phone says he has a method to eliminate that headache!

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Published on 1 week, 1 day ago

Awkward Tuesday: Baby Monitor Drama

What if a family member overhears something they weren't supposed to, and now the holidays are going to be EXTRA WEIRD unless you make a phone call with our help? It's happening right here in your Aw…

Published on 1 week, 2 days ago