Awkward Tuesday: There's Something About Maya

Up next

Second Date Update: Bachelor Party of One

This may be the BIGGEST RED FLAG we’ve ever heard on a first date… yet somehow, they still hooked up afterwords?? See omnystudio.com/listener for privacy information.

. 17min 42sec

FULL SHOW: Jeff’s Plant Daddy Song, Bridal Bounty Date + Most Insane Reality Shows (1/23/26)

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: Friday, January ... Show more

. 1h 4min

Recommended Episodes

Awkward Tuesday: Carrot Top Jackpot

Brooke and Jeffrey

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.

. 16min 17sec

Second Date Update: Dragon Thumbs and Aroma Chums

Brooke and Jeffrey

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.

. 17min 33sec

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

Brooke and Jeffrey

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

. 36min 4sec

Awkward Tuesday: 15 Minutes of Gurt

Brooke and Jeffrey

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.

. 16min 17sec