Second Date Update Classics: High School Holiday Hangout + Trial By Separation

Part 1 One of our listeners thought inviting a guy over might save her from spending time with her parents while home for the holidays… but we're going to hear how badly it backfired.  Part 2 The guy in today’s Second Date has been off the market for a decade and after his first date back in the game he’s getting left on read!See omnystudio.com/listener for privacy information.

One person almost ended up in tears just 9 holes into a mini-golf date..and our listener says it’s all his fault! We’ll have him explain coming in your Second Date Update podcast!See omnystudio.com/listener for privacy information.

One of our listeners had a drunken night at the bar and it led to an entire year of silence between her and her sister. Now she wants our help reuniting the family with a Closure Call!See omnystudio.com/listener for privacy information.

One of our listeners planned a first date to last 5 full days with a woman he had never even met before! We’ll hear what happened in your Second Date Update podcast!See omnystudio.com/listener for privacy information.

In your Awkward Tuesday Phone Call, one of our listeners is convinced her brother is hiding a big secret from the family, and she wants to reveal it with our help!See omnystudio.com/listener for privacy information.

A quick trip to move his car ended up being a HUGE mistake for our listener, and it sent his date WILDLY OFF TRACK. Hear how it went down in a Second Date Update!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, December 17th, 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 1 After we totally botched a Second Date for a guy a few months ago, he’s back and at this point we’re not sure if he’s trolling us or just likes the punishment. We can't let him down this time! Part 2 Imagine if you went on a date with a coworker and after the hang out, MULTIPLE PEOPLE are now avoiding you. It happened to one of our listeners and you can hear why in a Second Date!See omnystudio.com/listener for privacy information.

One of our listeners turned a super awkward moment into an actual MEET CUTE that almost seemed TOO perfect. You’ll hear it in your Second Date Update podcast!See omnystudio.com/listener for privacy information.

One of our listeners turned a super awkward moment into an actual MEET CUTE that almost seemed TOO perfect. You’ll hear it in your Second Date Update podcast!See omnystudio.com/listener for privacy information.