Masked Speaker: My Ex's Mom

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 says HER MOM may have accidentally ruined her chance with a guy and its all because of what mom needed from her daughter in the MIDDLE of a date.See omnystudio.com/listener for privacy information. 

If you asked a million people if they thought the surprise one of our listeners had for the woman he was dating was a good idea, NOBODY would say “YES!”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!    In your Awkward Tuesday Phone Call, one of our listeners is convin ... Show More

One of our listeners made her date laugh so hard that something embarrassing slipped out and she’s worried it’s the reason he’s not calling back!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. 

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 overheard their husband saying something VERY s ... 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

She hadn't spoken to her dad in months, so Producer Keity was so excited to call and catch up, but when he answered, the conversation didn't go as expected. Is she right to feel pissed? Hosted on Acast. See acast.com/privacy for more information. 

One of our listeners hadn’t thought about her ex-boyfriend in years until she got a random DM from a complete stranger… and what it said left us all shocked!See omnystudio.com/listener for privacy information. 

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.