Second Date Update: Flea Market Find

The woman we call in today’s Awkward Tuesday Phone Call might be the most brutal, ruthless, and vile person we’ve ever had on the show. She’s the sister of one of our listeners and we can’t believe what happened when he called to apologize to her!See omnystudio.com/listener for p ... Show More

Andre managed to cancel plans on Kim NOT ONCE, but TWICE in the same night. Is that too much to come back from? Find out in your Second Date Update podcast!See omnystudio.com/listener for privacy information. 

Every Sunday, we will be hosting 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: Friday, July 3rd, 2026 Curious if we look as bad as we sound? Follow us @Brookea ... Show More

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. 

One of our listeners is on the line to tell us about the SURPRISE LOCATION he brought a woman to to try and win her over. Hear where it was in a brand new Second Date Update podcast!See omnystudio.com/listener for privacy information. 

<p>For SURE, the most ANNOYING part of dating apps&hellip;.. is all the wasted energy you put in, getting to know someone really ONE&hellip; Only to never ACTUALLY meet up with them in person&hellip; And our listener on the phone says he has a method to eliminate that headache&he ... Show More

Our listener on the phone today claims his date said one specific thing to their waiter that wasn't just a green flag...but made him instantly realize she was relationship material! You’ll hear what it was in your brand new Second Date Update! Get your 2nd Date Update Merch For A ... Show More

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

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. 

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 was DITCHED on a date in a BRAZEN way and so today we’re on the hunt for ANSWERS in your Second Date Update podcast!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. 

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!!See omnystudio.com/listener for privacy information.