Second Date Update: Bachelor Party of One

The guy on the phone today asked out someone that he works with and we DID NOT expect to hear what happened after that! Find out what it is in your Second Date Update podcast!See omnystudio.com/listener for privacy information.

You never know what someone is gonna say when they think no one is listening. One of our listeners overheard their employee say something, and now we have an Awkward Tuesday Phone Call on our hands!See omnystudio.com/listener for privacy information.

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.

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 23rd, 2026 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 The guy on the phone today says he managed to pull a woman WAY out of his league, and it's all thanks to ONE move he pulled at the very end of the date!  Part 2 One of our listeners says he doesn’t need help getting a hold of the woman he dated… he needs our help to avoid criminal prosecution instead! See omnystudio.com/listener for privacy information.

One of our listeners unintentionally did something at the EXACT SAME TIME as his date, and he says it’s a sign of something HUGE! Hear what it is coming up in your Second Date Update podcast!See omnystudio.com/listener for privacy information.

It’s back by popular demand and against Brooke’s better judgment: We’re doing an all new edition of Brooke Breaks You Up!See omnystudio.com/listener for privacy information.

The guy on the phone today is a member of the “first timers club.” What’s the first timers club, exactly? Find out for yourself when we do a Second Date Update!See omnystudio.com/listener for privacy information.

One of our listeners says the family she babysits for owes her a lot of money... And because they won't pay up, she's ready to confront them in an Awkward Tuesday Phone Call!See omnystudio.com/listener for privacy information.

One of our listeners has a unique technique in order to give herself a pick-me-up on a date. And not only did it work for her, it led her to a guy she really likes too! Hear her strategy in your Second Date Update!See omnystudio.com/listener for privacy information.