Yesterday

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 feedback...but please send all negative reviews to Jeffrey. FULL SHOW: F ... Show More

1h 5m

Nov 22

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 barista and says she did something she would ... Show More

37 m

Nov 21

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 listeners we've ever had on the show!See <a href=" ... Show More

19m 22s

Apr 2025

Second Date Update: That Name Sounds Familiar

For SURE, the most ANNOYING part of dating apps….. is all the wasted energy you put in, getting to know someone really ONE… Only to never ACTUALLY meet up with them in person… And our listener on the phone says he has a method to eliminate that headache&he ... Show More

16m 27s

Jun 2025

Second Date Update: 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 brand new Second Date Update!See omnystudio.com/listener for privacy information.

16m 55s

Jul 2025

Second Date Update: Down In The Dumps

It’s SHOCKING to learn where the listener on the phone met a new love interest today, and it’s even more shocking that he somehow swung that interaction into a date! Hear the where, why and how coming up in your Second Date Update!See omnystudio.com/listener for privacy informati ... Show More

17 m

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

Sep 26

Second Date Update: Dutch Isn't Just A Language

The guy on the phone today says he bonded with his date over their shared HATE for one specific thing… But now she’s not calling back? Maybe we can get her to explain coming up in your Second Date Update!See omnystudio.com/listener for privacy information.

16m 55s

Aug 29

Second Date Update: Too Handy Not Handsy

After today’s Second Date Update you might agree with us that dating apps can be used for WAY more than just dates! See what we mean in the podcast!See omnystudio.com/listener for privacy information.

17m 31s

Apr 2025

Second Date Update: 3rd Times A Yawn

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! Catch what it is in a new Second Date Update! Get your 2nd Date Update Merch For A Cause <a hre ... Show More

17m 41s

Oct 25

Second Date Update Classics: 10 Pin Mixup + Pop Goes the Relationship

Part 1How badly are you willing to embarrass yourself if it means getting a date with that special person? One of our listeners went to the limit LIVE ON AIR and you get to hear it!Part 2A listener on the phone today says his first kiss with his date left a LOT to be desired… and ... Show More

36m 4s

Sep 22

Second Date Update: Facebook KO

The listener in today’s Second Date Update says that if we can’t help him, it’ll be the first time EVER that he’s been rejected by a woman! The high stakes call is happening in the podcast!See omnystudio.com/listener for privacy information.

16m 30s

Aug 2024

Second Date Update: Dine For One But I'm Not Done

The listener on the phone says her date ended up with some unexpected extra guests… but it’s actually kind of sweet how it all came together. Hear what happened in a Second Date podcast!See omnystudio.com/listener for privacy information.

17m 15s

Second Date Update: That Name Sounds Fam...