Awkward Tuesday: Unhappy Birthday

Every Sunday, we host one of our FULL HOUR episodes from our main show feed, Brooke & Jeffrey! We'd love to hear your feedback...but please send all negative reviews to Jeffrey. FULL SHOW: Friday, October 16th, 2026 Curious if we look as bad as we sound? Follow us @BrookeandJeffr ... Show More

Part 1 Nick is willing to tell us the MOST EMBARRASSING date night of his life… in hopes it will get him another shot with the woman he loves. Will it be worth the humiliation? Part 2 We have NO IDEA who we’re dialing in today’s Second Date Update, we have a number, and a sneakin ... Show More

Kyle made ONE SLIGHT adjustment to his dating profile and he ended up matching with a woman he calls “The real deal.” So why does he need our help? We’ll figure it out in your Second Date Update!See omnystudio.com/listener for privacy information. 

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. 

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. 

One of our listeners needs help texting someone he usually avoids to ask for a huge favor... And the answer could either MAKE or BREAK his entire Valentine's Day plans with his girlfriend! Let's see if we can get it done in a brand new Textual Healing.See omnystudio.com/listener ... Show More

Today's Masked Speaker wanted to surprise his girlfriend with something she ALWAYS wanted and it turned into a TOTAL DISASTER...See omnystudio.com/listener for privacy information. 

In today's Awkward Tuesday Phone Call, we’re helping one listener recover from an office holiday party that he says was the “GREATEST NIGHT” of his life… until his boss saw what he was doing…See omnystudio.com/listener for privacy information. 

One of our listeners says his BIGGEST relationship problem all started when he went to get a haircut… and when he got home… everything got weird...See omnystudio.com/listener for privacy information. 

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 he got an UNSOLICITED photo from a woman that left him speechless… in a bad way. See omnystudio.com/listener for privacy information. 

One of our listeners says it took her less than 12 hours from meeting a guy to completely ruining her chances. Find out how she did it coming up in your Awkward Tuesday Phone Call! See omnystudio.com/listener for privacy information.