Today

Second Date Update: Hired A Hinge Coach

The guy on the phone today hired a PRO dating coach, and says he learned one line that worked INSTANTLY to attract a quality woman. You can STEAL it once you find out what it is in your Second Date Update!See omnystudio.com/listener for privacy information.

18m 25s

Yesterday

FULL SHOW: Errand of Love Date, AI Sabotaging Our Show + Brooke’s Ruining Our YouTube (2/4/26)

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: Wednesday, Febr ... Show More

1h 8m

Feb 7

Second Date Update Classics: Car Talk + I Woke Up Where?

Part 1 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! Part 2 One of our listeners needs our help piecing together his night because he woke up not in his bed, n ... Show More

36m 52s

Jun 2025

Awkward Tuesday: Prenup or Pre-NOPE

One of our listeners has a looming conversation coming up and it’s one of the most difficult things you could ever talk about with a loved one. Before it happens they want our help via an Awkward Tuesday Phone Call!See omnystudio.com/listener for privacy information.

17m 30s

Oct 2024

Awkward Tuesday: Bullied By My Exes Kid

One of our listeners had her daughter come home in tears and she says the only way to fix it is if we helped her a brand new Awkward Tuesday Phone Call!See omnystudio.com/listener for privacy information.

15m 39s

Apr 2025

Awkward Tuesday: 15 Minutes of Gurt

How do you tell someone you love that their wildest dream might not be achievable? One of our listeners has that very problem with her boyfriend and she chose to email us for an Awkward Tuesday Phone Call!See omnystudio.com/listener for privacy information.

16m 17s

Jul 2024

Awkward Tuesday: Party Saviors

One of our listeners says it took her less than 12 hours from meeting a guy to completely ruining her chances. Find out how she did it coming up in your Awkward Tuesday Phone Call! See omnystudio.com/listener for privacy information.

16m 55s

Apr 2023

Awkward Tuesday: Scammer In The House Right Now

We got an URGENT email from a listener saying he needs our help getting a STRANGER out of his house RIGHT NOW. It’s an emergency Awkward Tuesday Phone Call!See omnystudio.com/listener for privacy information.

16m 9s

Oct 2025

Awkward Tuesday: Tinder Surprise

One of our listeners asked us for help with an Awkward Tuesday Phone Call but ended up BLINDSIDING us and his girlfriend at the same time. You gotta hear it in the podcast!See omnystudio.com/listener for privacy information.

17m 24s

Jan 2025

Awkward Tuesday: Carrot Top Jackpot

One of our listeners is about to get fantastic news… His wife went on a girls trip to Vegas and maybe one of the best things ever just happened to her… in your Awkward Tuesday Phone Call!See omnystudio.com/listener for privacy information.

16m 17s

Oct 2025

Awkward Tuesday: Buddy Roommate Sitch

Something UNWELCOME has been living in our listeners apartment, and it’s HIS OWN FRIEND. We’re using today’s Awkward Tuesday Phone Call to try and break up a living situation while saving a friendship!See omnystudio.com/listener for privacy information.

18 m

Jul 2023

Awkward Tuesday: The Prank That Went Too Far

The woman in today’s Awkward Tuesday Phone Call almost screwed up her whole relationship just for a social media prank video. Things are gonna get messy when we get her on the podcast!See omnystudio.com/listener for privacy information.

15m 27s

Mar 2025

Second Date Update: Dragon Thumbs and 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.

17m 33s

Awkward Tuesday: Stepmom Thirst Trap