Awkward Tuesday: Dark Side of the Costume Contest

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.

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.

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 omnystudio.com/listener for privacy information.

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, October 22nd, 2025 Curious if we look as bad as we sound? Follow us @BrookeandJeffrey: Youtube Instagram TikTok BrookeandJeffrey.comSee omnystudio.com/listener for privacy information.

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 now he wants our help fixing their issue in a Second Date Update podcast.See omnystudio.com/listener for privacy information.

One of our listeners found his PERFECT MATCH and it wasn’t on one of the popular dating apps you’ve probably heard of. We’ll reveal which dating site you’re probably gonna want to sign up for in your Second Date Update podcast!See omnystudio.com/listener for privacy information.

We NEVER thought we’d hear from this couple again after the FIRST time they came on our show. But they’re back today for a Second Date Update UPDATE! Stick around to hear how they've been since the first time we met them!See omnystudio.com/listener for privacy information.

The guy on the phone today didn’t use a pickup line or a smooth move, he did something so simple, even ALEXIS said it would have worked on her! Find out what it was in the Second Date Update podcast!See omnystudio.com/listener for privacy information.

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.

The guy on the phone today ended up SCREAMING on his date, but not for any of the good reasons you’d expect. Find out why in your Second Date Update podcast!See omnystudio.com/listener for privacy information.