Awkward Tuesday: Don't Be A Negative Nanny

The guy on the phone today is a member of the “first timers club.” What’s the first timers club, exactly? Find out for yourself when we do a Second Date Update!See omnystudio.com/listener for privacy information.

One of our listeners says the family she babysits for owes her a lot of money... And because they won't pay up, she's ready to confront them in an Awkward Tuesday Phone Call!See omnystudio.com/listener for privacy information.

One of our listeners has a unique technique in order to give herself a pick-me-up on a date. And not only did it work for her, it led her to a guy she really likes too! Hear her strategy in your Second Date Update!See omnystudio.com/listener for privacy information.

We're trying out a new idea for our fans of the 2nd Date Update! 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: Wednesday, January 14th, 2026 Curious if we look as bad as we sound? Follow us @BrookeandJeffrey: Youtube Instagram TikTok BrookeandJeffrey.comSee omnystudio.com/listener for privacy information.

Part 1 A little drawing on a cocktail napkin didn’t go the way our listener planned, and neither did his date night! You’ll understand why in the Second Date Update. Part 2 Just when you thought nothing good happens on airplanes anymore, one of our listeners met a woman on a flight and his story might inspire everyone listening!See omnystudio.com/listener for privacy information.

The guy on the phone today got caught showing up to his date after getting dropped off by ANOTHER WOMAN! We’re readying our battle stations for a contentious Second Date Update!See omnystudio.com/listener for privacy information.

One of our listeners asked his date a question that was RUDE, INSENSITIVE, and INAPPROPRIATE… at least we thought at first… Now he’s back for a special Second Date Update UPDATE!See omnystudio.com/listener for privacy information.

Ethan started his night meeting one woman, and ended up with a completely different one at his table by the end of the night! He’s desperate for a Second Date Update and we’re gonna give him one!See omnystudio.com/listener for privacy information.

99.9% of boyfriends would NEVER ask their girlfriends what the guy on the phone today asked his. Now he wants our help with an Awkward Tuesday Phone Call!See omnystudio.com/listener for privacy information.

All the guy on the phone today had to do to make himself PERFECT for his date is change TWO PHYSICAL things about himself… It backfired and now he wants a Second Date Update! See omnystudio.com/listener for privacy information.