Second Date Update Classic: Catching Fee...

A part-time babysitting job led one of our listeners into our email where she’s trying to figure out how to confront her “boss” about how she’s been treated! It's your Awkward Tuesday Phone Call!See omnystudio.com/listener for privacy information. 

Meghan told herself she’d only go out for “one drink” but that night spiraled out of control and now she needs OUR HELP to fix her mistakes in your Second Date Update!See omnystudio.com/listener for privacy information. 

Every Sunday, we host one of our FULL HOUR episodes from our main show feed Brooke & Jeffrey, and incase you missed it, here's our extra spooky Halloween show! FULL SHOW: Friday, October 30th, 2026 Curious if we look as bad as we sound? Follow us @BrookeandJeffrey: YouTube Instag ... 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

Part 1 This might be one of the first International Second Dates we’ve ever done! So come take a ride with us in an ultra-classy Second Date podcast. Part 2 A fun activity to go along with dinner is normally a great date... NOT TODAY. The guy on the phone botched his night and no ... Show More

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. 

There’s a thin line between sharing and OVER-sharing. One of our listeners wished she had learned that lesson BEFORE texting her guy after their date then we wouldn’t be in the position to help her with a Second Date Update!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 1How badly are you willing to embarrass yourself if it means getting a date with that special person? One of our listeners went to the limit LIVE ON AIR and you get to hear it!Part 2A listener on the phone today says his first kiss with his date left a LOT to be desired… and ... Show More

There’s some topics you just don’t bring up on a first date. One of our listeners didn’t follow that rule and now it’s no surprise he needs our help in a brand new Second Date podcast!See omnystudio.com/listener for privacy information. 

Part 1 A beautiful woman asked one of our listeners to take her out on a date… to a place she HATES! Why would she want that? We’ll get her to come clean in your Second Date Update. Part 2 The entire show was very surprised by how today’s Second Date finished. And we think all ou ... Show More

Something was EXPELLED from the body of one of our listeners while on a date, and while it wasn’t gross, it did happen for over an hour....But it’s not dissuading our listener from trying to get a Second Date!See omnystudio.com/listener for privacy information. 

The listener who needed our help with a Second Date shared a juicy detail from their first meetup that had us all floored, but made us promise to not bring it up when we called his date. We’re always up for a challenge though!See omnystudio.com/listener for privacy information.