Awkward Tuesday: Haunting of Boyfriends Past

It has a 0% success rate but that’s not gonna stop us! We sent Ashton out for REVERSE TRICK OR TREATING to see if someone will let him into their home!See omnystudio.com/listener for privacy information.

One of our listeners was SO RELAXED on her night out with Vince, that she did something unintentional and kind of embarrassing. She thinks it’s probably why she needs our help with a Second Date Update!See omnystudio.com/listener for privacy information.

Today’s Halloween Edition of the Awkward Tuesday Phone Call is a mortifying conversation between two people who REALLY don’t like each other anymore!See omnystudio.com/listener for privacy information.

One of our listeners said he met a woman during the spookiest time of the year but he never expected to be GHOSTED! We’re investigating and digging in for him in your Halloween Second Date Update!See omnystudio.com/listener for privacy information.

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: Wednesday, October 21st, 2026 Curious if we look as bad as we sound? Follow us @BrookeandJeffrey: YouTube Instagram TikTok BrookeandJeffrey.comSee omnystudio.com/listener for privacy information.

Part 1 Jake and Kim bonded on their date over their shared HATE for one specific thing… But now she’s not calling back? Maybe we can get her to explain coming up in your Second Date Update! Part 2 All Anthony had to do to make himself PERFECT for his date is change TWO PHYSICAL things about himself…and of course it completely backfired.See omnystudio.com/listener for privacy information.

Daniel was DESPERATELY trying to avoid answering one specific question on his date with Lilly. It got asked, it DIDN’T go well, and now he wants our help figuring out how to put the pieces back together in your Second Date Update!See omnystudio.com/listener for privacy information.

The guy on the phone for today’s Awkward Thursday Phone Call DESPERATELY needs our help because his HOA is threatening to FINE him hundreds of dollars if he goes through with his favorite Halloween tradition!See omnystudio.com/listener for privacy information.

One of our listeners has a crush on his co-worker and he came up with a plan to show her! It involves a microwave and a wilted bowl of salad… See omnystudio.com/listener for privacy information.

Two weeks after tying the knot, Katherine wants an apology from one of her unruly family members for the way he acted at her wedding. Its your Awkward Tuesday Phone Call!See omnystudio.com/listener for privacy information.