Second Date Update: Too Late To Apologiz...

FULL SHOW: Monday, August 25th, 2025 Curious if we look as bad as we sound? Follow us @BrookeandJeffrey: Youtube Instagram TikTok BrookeandJeffrey.comSee omnystudio.com/listener for privacy information. 

We scoured the back pages of Craigslist to find the best (or is it worst?) entries from their Missed Connections section! Whether you're a hopeless romantic or just plain hopeless, this might be the place for you!See 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. 

The guy in today’s Second Date wants our help to apologize for saying one of the rudest things we’ve ever heard on this show. Is it too little too late though?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. 

Spread Em - The guy in today's Second Date already knows he did something wrong. The thing is, he was pretty much guaranteed a second date before he screwed up this big. So now he wants a chance to apologize to Mariella and try to reclaim some sense of dignity. 

Spread Em - The guy in today's Second Date already knows he did something wrong. The thing is, he was pretty much guaranteed a second date before he screwed up this big. So now he wants a chance to apologize to Mariella and try to reclaim some sense of dignity. 

The guy in today’s Second Date Update made a BOLD REQUEST before we even called his date. Was it fair? Sure! Was Brooke offended by it? Yep! Get your 2nd Date Update Merch For A Cause HERE!See omnystudio.com/listener for privacy information. 

You won’t believe how the guy in today’s Second Date managed to score a date with a Perfect 10! He got the first date, but now he needs our help trying to wrangle another…See omnystudio.com/listener for privacy information. 

We might have had one the most awkward “jump to conclusion” moments we’ve ever had on this show and we’re just shocked we didn’t screw it up for the guy. Hear it in your Second Date Update podcast!See omnystudio.com/listener for privacy information. 

Little mistakes are okay on a first date, but today's Second Date had one BIG mistake and we're hoping it didn't happen on purpose...See omnystudio.com/listener for privacy information. 

One of our listeners is worried her gratitude for a gift was BADLY misinterpreted as rude and now she wants our help 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.