Awkward Thursday: No Free Family Dinner

Awkward Thursday: No Free Family Dinner

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#7 Second Date Update of 2025: Street Walker Love Story

One of our listeners turned a super awkward moment into an actual MEET CUTE that almost seemed TOO perfect. You’ll hear it in your Second Date Update podcast!See omnystudio.com/listener for privacy information. 

Brooke Breaks You Up: Holiday Edition

It’s one of the most controversial segments in the history of our show, but today it comes with a twist. It's the Holiday Edition of Brooke Breaks You Up!See omnystudio.com/listener for privacy information. 

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Awkward Tuesday: Bullied By My Exes Kid
Brooke and Jeffrey

One of our listeners had her daughter come home in tears and she says the only way to fix it is if we helped her a brand new Awkward Tuesday Phone Call!See omnystudio.com/listener for privacy information. 

Awkward Tuesday: Prenup or Pre-NOPE
Brooke and Jeffrey

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. 

Awkward Tuesday: Bridesmaid Contract
Brooke and Jeffrey

What do you say to your best friend if you know they’re about to make the biggest mistake of their life? Find out what we suggest coming up in a new Awkward Tuesday Phone Call podcast!See omnystudio.com/listener for privacy information. 

Awkward Tuesday: 15 Minutes of Gurt
Brooke and Jeffrey

How do you tell someone you love that their wildest dream might not be achievable? One of our listeners has that very problem with her boyfriend and she chose to email us for an Awkward Tuesday Phone Call!See omnystudio.com/listener for privacy information.