Yesterday

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 <a href="https://omnystudio.com/listener">omnystudio.com/listener</a> for privacy infor ... Show More

19m 50s

Nov 24

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 <a href="https://omnystudio.com/listener">omnystudio.com/listener</ ... Show More

18m 42s

Nov 23

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

May 2025

Second Date Update: Hang Up On Him

One of our listener’s first kiss happened but her second date never did! So we’re gonna do everything in our power to get to the bottom of it in a brand new Second Date Update! Get your 2nd Date Update Merch For A Cause HERE!See omnystudio.com/listener for privacy information.

17m 14s

May 2025

Second Date Update: A Picture Says A Thousand Icks

Our listener on the phone today claims his date said one specific thing to their waiter that wasn't just a green flag...but made him instantly realize she was relationship material! You’ll hear what it was in your brand new Second Date Update! Get your 2nd Date Update Merch For A ... Show More

17m 1s

Jan 2025

Second Date Update: Fetching Feelings

One of our listeners is on the line to tell us about the SURPRISE LOCATION he brought a woman to to try and win her over. Hear where it was in a brand new Second Date Update podcast!See omnystudio.com/listener for privacy information.

16m 5s

Jun 2025

Second Date Update: Best Date of My Life

The kiss that happened at the end of our listener's date was either the cutest, most spontaneous thing ever, or the cringiest, most awkward interaction of all time. Decide for yourself after the new Second Date Update!See omnystudio.com/listener for privacy information.

17m 58s

Oct 4

Second Date Update Classics: Ex-Aversary + Lady In Red

Part 1 The guy from today’s Second Date Update said he got a text that completely BAFFLED HIM considering how good his first date went...You’ll hear about the weird message he received coming up. Part 2 An interaction on the dance floor led to one of the most embarrassing situati ... Show More

34m 34s

Apr 2025

Second Date Update: Couch Crush

Our listener met a good looking lady at a FURNITURE store of all places. You don’t hear that one too often! We’ll share his story in a brand new Second Date Update podcast! Get your 2nd Date Update Merch For A Cause HERE!See omnystudio.com/listener for privacy information.

17m 52s

Mar 2025

Second Date Update: Phone Paux

One of our listeners became best friends with a fellow gym-goer before he decided to ask her on a date… You’ll hear how he did it in your Second Date Update podcast! Get your 2nd Date Update Merch For A Cause HERE!See omnystudio.com/listener for privacy information.

17m 51s

Apr 2025

Second Date Update: The Good, The Bad & The Fugly

The woman in today’s Second Date says she waits 30 DAYS before meeting up with a guy for the second time. You’ll never believe her reasons why, but you can hear it in the podcast! Get your 2nd Date Update Merch For A Cause HERE!See omnystudio.com/listener for privacy information.

17m 3s

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

Apr 2025

Second Date Update: Car Talk

The woman on the phone today got an INTERESTING surprise when she got into her date's car, and that kind of weirdness is something we can all get behind on this show! New Second Date Update podcast is all yours! Get your 2nd Date Update Merch For A Cause HERE!See omnystudio.com/l ... Show More

17m 14s

Second Date Update: Flirt and Observe