Awkward Tuesday: Prenup or Pre-NOPE

Part 1 One of our listeners tried out the dating app PLENTY OF FISH… and you’re not gonna believe what happened on her very first meet up! Part 2 One of our listeners WISHES he did a better job cleaning up his car, because his entire night was ruined when his date found something ... 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, August 7th 2026 Curious if we look as bad as we sound? Follow us @BrookeandJeffrey: Youtube Instagram TikTok BrookeandJeffrey.comSee omnystudio.com/listener for privacy information. 

One of our listeners has a looming conversation coming up and it’s one of the most difficult things you could ever talk about with a loved one. Before it happens they want our help via an Awkward Tuesday Phone Call!See omnystudio.com/listener for privacy information. 

One of our listeners needs help asking a VERY LOADED question to his girlfriend… We’ll try to help him out in your Awkward Tuesday Phone Call podcast!See omnystudio.com/listener for privacy information. 

One of our listeners is dealing with a difficult type of neighbor drama. You’re gonna want to hear our advice coming up in a brand new Awkward Tuesday Phone Call!See omnystudio.com/listener for privacy information. 

Our listeners love dysfunctional relationships so much, we didn't wanna deprive you. Here's a segment from our Full Show feed that may have even more drama than a Second Date Update. Let us know what you think!  One of our listeners needs our help because a GIFT she got for her w ... Show More

We’ve done countless Awkward Tuesday Phone Calls over the years but today is the first one where we’re helping someone call a complete STRANGER… with a foreboding warning…See omnystudio.com/listener for privacy information. 

Our listeners love dysfunctional relationships so much, we didn't wanna deprive you. Here's a segment from our Full Show feed that may have even more drama than a Second Date Update. Let us know what you think!  One of our listeners is willing to put herself in a very uncomfortab ... Show More

One of our listeners is facing a HUGE life moment, and the only person standing in his way is his terrifying FUTURE FATHER IN-LAW. He’ll make a terrifying Awkward Tuesday Phone Call in the podcast!See omnystudio.com/listener for privacy information. 

One of our listeners needs our help with an IN-LAW INFESTATION. We’re gonna try to assist and get her mother in law out of her home in a brand new Awkward Tuesday Phone Call!See omnystudio.com/listener for privacy information. 

Our listeners love dysfunctional relationships so much, we didn't wanna deprive you. Here's a segment from our Full Show feed that may have even more drama than a Second Date Update. One of our listeners emailed us for help with a situation SO delicate, that if he can’t figure ou ... Show More

Our listeners love dysfunctional relationships so much, we didn't wanna deprive you. Here's a segment from our Full Show feed, 'Brooke and Jeffrey',  that may have even more drama than a Second Date Update. Let us know what you think!  One of our listeners has a dilemma. Her frie ... Show More