Second Date Update Classic: Cowboy Confusion

FULL SHOW: Monday, May 11th, 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. 

One of our listeners said she made the first move and left her comfort zone to hit on a handsome guy. That decision lead her here but maybe we can help her finish strong with a Second Date Update! Get your 2nd Date Update Merch For A Cause HERE!See omnystudio.com/listener for pri ...  Show more

One of our listeners made a BIG ASK, a request we never heard before… telling a guy if he wanted any shot at dating her he had to do THIS first. Find out what it is in your Second Date Update podcast!! Get your 2nd Date Update Merch For A Cause HERE!See omnystudio.com/listener fo ...  Show more

Something happened to our listener on his way to the first meetup with his date, and it changed the trajectory of their entire night! Hear what happened in a new Second Date Update podcast! Get your 2nd Date Update Merch For A Cause HERE!See omnystudio.com/listener for privacy in ...  Show more

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.