Podcast Episodes

Second Date Update: 30 for 30

One of our listeners is experimenting in a new dating strategy, all about the YEAR she was born. Find out what she’s doing in your Second Date Update podcast!

See omnystudio.com/listener for privacy i…

Published on 1 month, 3 weeks ago

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.co…

Published on 1 month, 3 weeks ago

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.

Published on 1 month, 3 weeks ago

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 31s…

Published on 1 month, 3 weeks ago

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 listener…

Published on 1 month, 3 weeks ago

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/l…

Published on 1 month, 3 weeks ago

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.

Published on 1 month, 3 weeks ago

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 pri…

Published on 1 month, 3 weeks ago

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…

Published on 1 month, 4 weeks ago

Second Date Update: Romeo and Ghouliet

The guy in today’s Second Date works at a haunted house and is looking to reconvene with a coworker he once dated. It’s Halloween week and we’re hoping to treat them both right in the podcast!

See omn…

Published on 1 month, 4 weeks ago