Podcast Episodes

#9 Second Date Update of 2025: Dragon Thumbs & Aroma Chums

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.

Published on 1 week, 3 days ago

FULL SHOW: Holiday Men Hack Date, Jose’s Midnight Meet Up + Smaller is Better for Jeff (12/10/25)

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 week, 4 days ago

Second Date Update Classics: 3rd Times a Yawn + Super Kid Shames the Day

Part 1

The guy on the phone today told us he’s fed up with being friend-zoned, and he wants to get ahead of things with a bizarre new plan we’ve never tried before! 

Part 2

The guy on the phone says …

Published on 1 week, 5 days ago

#10 Second Date Update of 2025: Give Him The Golden

One of our listeners made a BIG ASK, a request we never heard before… telling a guy if he wanted any shot at dating her, he had to do THIS first. Find out what it is in your Second Date Update podcas…

Published on 1 week, 6 days ago

Textual Healing: Dog Disturbance

One of our listeners is having a problem dealing with her next door neighbor and it’s slowly ruining her life. We’ll try to help her with some Textual Healing!

See omnystudio.com/listener for privacy …

Published on 2 weeks ago

Second Date Update: Does This Smell Like Your Mom?

One of our listeners says there's a sneaky spot where you can meet cute guys, and it ONLY happens during the holidays. You’ll find out where that is coming up in your Second Date Update podcast!

See o…

Published on 2 weeks, 1 day ago

Awkward Tuesday: Knock Off No No

The woman on the phone today is ready to CONFRONT the person who has been scamming her for the past 3 years. It also happens to be her boyfriend…

See omnystudio.com/listener for privacy information.

Published on 2 weeks, 2 days ago

Second Date Update: He Bought Me A Star

It can be so difficult to find a guy who does the bare minimum, but the woman on the phone today found a guy who is OUT OF THIS WORLD! We’ll let her explain why she wants to see her date again, in yo…

Published on 2 weeks, 3 days ago

FULL SHOW: The Last Hopeful Dater, Jeff’s Mom’s High Speed Chase & Alexis’ Car Casino (12/3/25)

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 2 weeks, 4 days ago

Second Date Update Classics: Double Roasted Turkey + 20 Treadmills of Love

Part 1 

One of our listeners met a guy in a peculiar way… by SAVING HIS LIFE! But why doesn’t he ever want to see her again? We’ll use a Second Date Update to find out.

Part 2

The woman on the phone …

Published on 2 weeks, 5 days ago