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

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.