Awkward Tuesday: I Want To Date My Frien...

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. 

Is it ever okay to date your friends EX? Don’t ask us, in fact, just get ‘em on the phone for an Awkward Tuesday Phone Call instead!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. 

Hey all, I am out on book tour and will return with an all new episode on Wednesday 5/14. In the meantime enjoy some fun calls from the past! Including a woman who is crushing hard on a friends ex, and doesn't know what to do. 

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!  The woman in today’s Awkward Tuesday Phone Call wants to preserve a ... Show More

Amber Whittington joins Mal to discuss the age-old question - when, if ever, and under what circumstances, is it okay to date your friend's ex? How do you navigate that conversation? Can you still be friends after that happens? Let us know your thoughts in the comments! JOIN OUR ... 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 says that a romantic spark is happening with her coworker and now she needs our help nudging this friendship with an Awkward Tuesday Phone Call!See omnystudio.com/listener for privacy information. 

Part 1When the listener on the phone described his date we got some creepy vibes. Are we reading the situation wrong or is he just misunderstood? Part 2The guy in today’s Second Date Update was brave enough to ask out a CUSTOMER from his JOB! It ended up being a great time, but w ... Show More

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 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.