Second Date Update: Like a Fine Wine

Second Date Update: Like a Fine Wine

One of our listeners (Henry) has very very specific taste in women. He likes his ladies on the Older side. There's nothing wrong with that. But he's upset that his date Jodi isn't calling him back after their night out. What went wrong? We'll find out in the Second Date Update.
(Image Courtesy: Joe Duty. Creative Commons)

See omnystudio.com/listener for privacy information.

Episoder(1965)

Awkward Tuesday: Girls Trip Mystery

Awkward Tuesday: Girls Trip Mystery

One of our listeners wants to find out the TRUTH of what happened when his girlfriend went on a GIRLS TRIP out of town… We’ll do our best to help in a new Awkward Tuesday Phone Call!See omnystudio.com/listener for privacy information.

4 Nov 18min

Second Date Update: Red Flag Test

Second Date Update: Red Flag Test

We needed the listener on the phone today to be 100% HONEST about what happened with his date, and that proved to be harder than we realized…See omnystudio.com/listener for privacy information.

3 Nov 18min

HALLOWEEN SHOW: Jeff’s Disney Villian Song, Boo’s & Booze Date + Ghost Hunter Prank (10/31/25)

HALLOWEEN SHOW: Jeff’s Disney Villian Song, Boo’s & Booze Date + Ghost Hunter Prank (10/31/25)

We didn't want you to miss out on our favorite show of the year... Halloween is our Superbowl! Enjoy all the spooky crazy fun from our main show feed, Brooke & Jeffrey! FULL SHOW: Friday, October 31st, 2025 Curious if we look as bad as we sound? Follow us @BrookeandJeffrey: Youtube Instagram TikTok BrookeandJeffrey.comSee omnystudio.com/listener for privacy information.

2 Nov 1h 5min

Second Date Update Classics: It's A Costume Dummy + Blackout Drunk Shuttlecock 

Second Date Update Classics: It's A Costume Dummy + Blackout Drunk Shuttlecock 

Part 1 The guy in today’s Second Date Update tried a pickup line that was cringey, not just on one level… but on MULTIPLE LEVELS and he quickly realized he needed our help. Part 2 One of our listeners found themselves in the middle of an epic house party and he thinks he found a girl he wants to get serious with… but something happened on the way over to the daiquiri mix… and we’re about to get to the bottom of it in your Second Date Update!See omnystudio.com/listener for privacy information.

1 Nov 36min

Second Date Update: Halloween Boos and Booze Bar Crawl

Second Date Update: Halloween Boos and Booze Bar Crawl

One critical moment told the ENTIRE story of our listener's date and now they BOTH can’t stop talking about it. Hear how it went down in your Halloween Second Date Update podcast!See omnystudio.com/listener for privacy information.

31 Okt 18min

Blind Love Is? Halloween Edition

Blind Love Is? Halloween Edition

Buckle up Boys and Ghouls, it's a special double-jam-packed HALLOWEEN EDITION of BLIND LOVE IS?See omnystudio.com/listener for privacy information.

30 Okt 18min

Second Date Update: Halloween Bean Dip Mystery

Second Date Update: Halloween Bean Dip Mystery

A family member showed up out of NOWHERE on our listener's date, and what happened next made everyone’s skin crawl. Catch it all in your Second Date Update podcast!See omnystudio.com/listener for privacy information.

29 Okt 18min

Awkward Tuesday: Dark Side of the Costume Contest

Awkward Tuesday: Dark Side of the Costume Contest

A new costume is causing MAJOR drama between a listener and his close friend, and he has no idea where else to turn! It’s a Halloween-themed Awkward Tuesday Phone Call!See omnystudio.com/listener for privacy information.

28 Okt 19min

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