Second Date Update: No Fun Top Gun

Part 1 One of our listeners says a DEAFENING silence happened after an awkward question from their waiter on their date, and now she’s not getting a call back. Part 2 The woman on the phone today claims that she discovered a place that is swarming with career driven, high-value m ... Show More

We're pitting the generations against each other with the ultimate trivia game, it's Brooke vs. Alexis!See omnystudio.com/listener for privacy information. 

FULL SHOW: Friday, July 17th, 2026 Curious if we look as bad as we sound? Follow us @BrookeandJeffrey: Youtube Instagram TikTok BrookeandJeffrey.comSee omnystudio.com/listener for privacy information. 

The guy in today’s Second Date tried to come up with a cool date idea, and he did. But once they were there he had to CONSTANTLY say “NO” to his date. Can we help get a “yes” back from her?See omnystudio.com/listener for privacy information. 

One of our listeners says his plan to impress his date and make her like him did NOT go how he wanted… in fact his night ended in physical pain! Hear it all in your 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. 

The guy in today’s Second Date is wondering if the surprise he prepared on the first date was TOO MUCH, and now wants our help to reconnect with the woman he might have scared away!See omnystudio.com/listener for privacy information. 

One of our listeners says HIS DATE asked him to do something UNUSUAL shortly after they sat down, and he thinks its part of why he’s not getting a call back. Get your 2nd Date Update Merch For A Cause HERE!See omnystudio.com/listener for privacy information. 

One of our listeners says his plan to impress his date and make her like him did NOT go how he wanted… in fact his night ended in physical pain! See omnystudio.com/listener for privacy information. 

Our listener on the phone today says his date set a boundary before they even met in person. He had to say “yes,” to get a shot at her, and now we’re trying to get her to say “Yes” to a Second Date!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. 

The guy on the phone today told us he’s fed up with being friend-zoned, and he wants to get ahead of things with a bizarre new plan we’ve never tried before! Catch what it is in a new Second Date Update! Get your 2nd Date Update Merch For A Cause HERE!See omnystudio.com/listener ... Show More

The guy in today’s Second Date has been out of the dating pool for a few years, and now after his first hangout isn’t calling him back, he wants our help of all things!