Second Date Update Classic: Age-Ja-Vu

FULL SHOW: Wednesday, June 10th, 2026 Curious if we look as bad as we sound? Follow us @BrookeandJeffrey: Youtube InstagramTikTok 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. 

What’s the opposite of a Wingman? Whatever you call it, that type of guy is what ruined our listeners date.  Now he wants our help to try and save it with a Second Date!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. 

Part 1 The guy in today’s Second Date is a PROUD single-dad, but he thinks it also might be the reason for the downfall of his first date. You’ll hear what happened in the podcast! Part 2 One of our listeners has a perfect little trick to learn EXACTLY what a guy is thinking at t ...  Show more

We conducted a mini-experiment with Brooke in today’s new Second Date and it helped us get into the unusual mindset of one of our listeners to try and find him a match!See omnystudio.com/listener for privacy information.