Second Date Update Classic: Halloween Ro...

We're pitting the generations against each other with the ultimate trivia game, it's Brooke vs. Alexis!See omnystudio.com/listener for privacy information. 

FULL SHOW: Friday, September 4th, 2026 Curious if we look as bad as we sound? Follow us @BrookeandJeffrey: YouTube Instagram TikTok BrookeandJeffrey.comSee omnystudio.com/listener for privacy information. 

Have a knack for trivia? Well, so does Brooke… Try to answer as many questions right as you can in 30 seconds. If you answer more correctly than Brooke, you win 100 bucks! Good luck!See omnystudio.com/listener for privacy information. 

The guy on the phone today wants to try and recreate his perfect first date all over again… exactly one year to the day. It involves wearing children’s costumes and it’s happening in a Second Date Update!See omnystudio.com/listener for privacy information. 

Part 1One of our listeners decided his goal was to bring the magic of RomComs to his dating life...Now we need to help him finish his love story!Part 2The guy on the phone says one text before the date started changed their ENTIRE NIGHT—Find out what it was in your Second Date Up ... Show More

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. 

One of our listeners decided his goal was to bring the magic of RomComs to his dating life. You’ll find out how during an all new Second Date Update!See omnystudio.com/listener for privacy information. 

Get your 2nd Date Update Merch For A Cause HERE! The guy in today’s Second Date Update has been on the show before, but today he gets the special opportunity for a First Date REDATE!See omnystudio.com/listener for privacy information. 

Part 1 The guy on the phone today says his date night included a blindfold and a bit of deception, but it turned out even better than he ever planned. Hear what happened in your Second Date podcast. Part 2 The guy in today’s Second Date Update flew across the ocean just to meet s ... Show More

The guy in today’s Second Date is wondering if the surprise he prepared on the first date was TOO MUCH, and now wants our help to reconnect with the woman he might have scared away!See omnystudio.com/listener for privacy information. 

Typically on a first date, you’re supposed to do something fun and not invite someone to your work... But the guy in today’s Second Date did the second option and now he’s calling us for help fixing his love life!See omnystudio.com/listener for privacy information. 

The guy on the phone for today’s Second Date Update says we need to get him ANSWERS, not just for his sanity, but for his FRIEND GROUP, who played a strange role in his date… Get your 2nd Date Update Merch For A Cause HERE!See omnystudio.com/listener for privacy information. 

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 ... Show More