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

<p>FULL SHOW: Wednesday, November 26th, 2025</p> <p>Curious if we look as bad as we sound? Follow us @BrookeandJeffrey:</p> <p><a href="https://www.youtube.com/c/BrookeandJeffrey">Youtube</a></p> <p><a href="https://www.instagram.com/brookeandjeffrey/?hl=en">Instagram</a></p> <p> ... Show More

<p>Have a knack for trivia? Well, so does Brooke&hellip; 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!</p><p>See <a href="https://omnystudio.com/listener">omnystudio.com/listener</a> for pri ... Show More

<p>The guy in today&rsquo;s Second Date Update has been on the show before, but today he gets the special opportunity for a First Date REDATE!</p><p>See <a href="https://omnystudio.com/listener">omnystudio.com/listener</a> for privacy information.</p> 

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. 

<p>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.</p><br/> <p>Hosted by Simplecast, an AdsWizz com ... 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!  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 OU ... Show More

One of our listeners THOUGHT his girlfriend was planning an epic birthday trip for him, until one text message shattered everything… and now he needs an Awkward Tuesday Phone Call!See omnystudio.com/listener for privacy information. 

The guy in today’s Awkward Tuesday Phone call is desperate to spark a romantic connection with someone he’s known for years. They’re not exactly friends… but they've been close for years...See omnystudio.com/listener for privacy information. 

One of our listeners THOUGHT she was doing the right thing lying to her boss and her company to get her friend hired, and in today’s Awkward Tuesday Phone Call we’ll find out how it turned into the worst decision she ever made!See omnystudio.com/listener for privacy information. 

One of our listeners asked us for help with an Awkward Tuesday Phone Call but ended up BLINDSIDING us and his girlfriend at the same time. You gotta hear it in the podcast!See omnystudio.com/listener for privacy information. 

Something UNWELCOME has been living in our listeners apartment, and it’s HIS OWN FRIEND. We’re using today’s Awkward Tuesday Phone Call to try and break up a living situation while saving a friendship!See omnystudio.com/listener for privacy information.