Masked Speaker: 23 & Daddy

FULL SHOW: Friday, October 9th, 2026 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. 

When we offered to send this couple on another date that WE PAY for, we never expected to get the answer back that we received. Hear one of the most bizarre endings to a Second Date Update ever!See omnystudio.com/listener for privacy information. 

One of our listeners was SHOCKED by the children’s birthday invite her son received… in fact, all the parents were so bothered by the strange instructions, she needs our help with an Awkward Tuesday Phone Call!See omnystudio.com/listener for privacy information. 

One of our listeners came across an overbearing mother and what went down between them is either gonna be the biggest misunderstanding ever, or the most awkward roommate convo of her life!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. 

A family member showed up out of NOWHERE on our listener's date, and what happened next made everyone’s skin crawl. Catch it all in your Second Date Update podcast!See omnystudio.com/listener for privacy information. 

One of our listeners is facing a HUGE life moment, and the only person standing in his way is his terrifying FUTURE FATHER IN-LAW. He’ll make a terrifying Awkward Tuesday Phone Call in the podcast!See omnystudio.com/listener for privacy information. 

David’s mother is a fantasist with a secret. But hers is the kind of strange secret that’s out in the open…sort of. As David grows up, he finds the intersection between drama and comedy in this tangled history. See omnystudio.com/listener for privacy information. Learn more about ... Show More

It’s SHOCKING to learn where the listener on the phone met a new love interest today, and it’s even more shocking that he somehow swung that interaction into a date! Hear the where, why and how coming up in an all new Second Date Podcast! See omnystudio.com/listener for privacy i ... Show More

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.