Second Date Update Classic: Red Envelope...

FULL SHOW: Friday, July 11th, 2025 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. 

When the woman on the phone today described her job to us we were SHOCKED… but is it something that would keep her from a happy dating life? Find out in a brand new Second Date Update!See omnystudio.com/listener for privacy information. 

If only finding a date was as easy as ordering your favorite drink. One of our listeners had the perfect girl right in front of him all thanks to a new dating event that even YOU might want to try! Get your 2nd Date Update Merch For A Cause HERE!See omnystudio.com/listener for pr ... Show More

One of our listeners came up with the perfect first date question. You might want to steal this one once you hear it!  Get your 2nd Date Update Merch For A Cause HERE!See omnystudio.com/listener for privacy information. 

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

What started as a romantic one on one date ended with our listener sandwiched between three gorgeous women all night! He’ll explain how he did it coming up in your Second Date Update podcast! Get your 2nd Date Update Merch For A Cause HERE!See omnystudio.com/listener for privacy ... 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. 

One of our listeners became best friends with a fellow gym-goer before he decided to ask her on a date… You’ll hear how he did it in your Second Date Update podcast! Get your 2nd Date Update Merch For A Cause HERE!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

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

One of our listeners turned a super awkward moment into an actual MEET CUTE that almost seemed TOO perfect. You’ll hear it in a brand new Second Date Update podcast! Get your 2nd Date Update Merch For A Cause HERE!See omnystudio.com/listener for privacy information. 

The woman on the phone today got an INTERESTING surprise when she got into her date's car, and that kind of weirdness is something we can all get behind on this show! New Second Date Update podcast is all yours! Get your 2nd Date Update Merch For A Cause HERE!See omnystudio.com/l ... Show More