Awkward Tuesday: Prenup or Pre-NOPE

Part 1 The woman in today’s Second Date has to defend her one weird habit that she swears is NATURAL, but it left all of us shocked. Part 2 One of our listeners was brave enough to introduce his date to his FAMILY on night one! Hear all about this bold new strategy in your Second ... Show More

FULL SHOW: Friday, August 22nd, 2025 Curious if we look as bad as we sound? Follow us @BrookeandJeffrey: Youtube Instagram TikTok BrookeandJeffrey.comSee 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. 

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 was FORCED to talk about money with his crush, and the reason WHY it’s the topic of conversation might be the craziest part. It's 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. 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 that may have even more drama than a Second Date Update. Let us know what you think!  One of our listeners has had a secret crush on his friend for 3 YEAR ... Show More

One of our listeners is freaking out over what his new stepmom just posted online...He says it has potential to ruin their entire family dynamic UNLESS he can convince her to take it down. That's why he's come to us for help in a brand new Awkward Tuesday Phone Call!See omnystudi ... Show More

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 came across an overbearing mother and what went down between them is either gonna be the biggest misunderstanding ever, or the most awkward roommate convo of her life!See omnystudio.com/listener for privacy information. 

One of our listeners says she LOVES her boyfriend just the way he is…. Except for ONE THING. She’ll explain why she needs him to STOP FOREVER coming up in a new Awkward Tuesday Phone Call!See omnystudio.com/listener for privacy information. 

Is there a way to BETRAY a friend… but POLITELY? One of our listeners wants to do that, but she has a good reason for it and wants our help with an Awkward Tuesday Phone Call!See omnystudio.com/listener for privacy information.