Second Date Update Classic: Cowboy Confusion

Every Sunday, we host 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: Tuesday, August 18th, 2026 Curious if we look as bad as we sound? Follow us @BrookeandJeffr ...  Show more

Part 1 Cory took a PLANE FLIGHT to hang out with Alison… but their date left a lot to be desired… We’ll try to fix their future in your Second Date Update podcast! Part 2 One of our listeners took a BOLD step when she made a move on a guy while he was working… and seconds later t ...  Show more

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

Part 1 The woman on the phone today saw a cute guy and although her first move was UNORTHODOX… apparently it worked! Part 2 There’s a thin line between sharing and OVER-sharing. One of our listeners wishes she had learned that lesson BEFORE texting her guy after their date... the ...  Show more

The woman on the phone today saw a cute guy and although her first move was UNORTHODOX… apparently it worked! Hear how in a brand new Second Date Update podcast!See omnystudio.com/listener for privacy information. 

Part 1 One of our listeners said she met a guy the other night who almost got her ARRESTED. So why does she want another date with him?? Time to find out! Part 2 The woman on the phone says both she AND her date were asked to leave bar trivia over the most ridiculous reason, but ...  Show more