Masked Speaker: Position Push-Out

Part 1 5 minutes into his date with Delilah, Jack realized he forgot something MAJORLY important. Hear what slipped his mind and how we’re helping him gain back ground! Part 2 The listener in today’s Second Date Update says that if we can’t help him, it’ll be the first time EVER ... Show More

We're pitting the generations against each other with the ultimate trivia game, it's Brooke vs. Alexis!See omnystudio.com/listener for privacy information. 

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. 

One of our listeners is FURIOUS after her date left her in the most embarrassing situation of her life… and now she wants not just answers, but REVENGE.See omnystudio.com/listener for privacy information. 

One of our listeners is FURIOUS after her date left her in the most embarrassing situation of her life… and now she wants not just answers, but REVENGE. Get your 2nd Date Update Merch For A Cause HERE!See omnystudio.com/listener for privacy information. 

Sometimes just one photo can raise the REDDEST of RED FLAGS and that happened to one of our listeners. She noticed something on a guys profile pic and now she wants our help finding him and getting him to explain. See omnystudio.com/listener for privacy information. 

One of our listeners was trying to walk a thin line in trying to get a man to notice her, and pulled a move that maybe went a little too far… See omnystudio.com/listener for privacy information. 

One of our listeners was so TURNED OFF by her date that instead of just escaping, she wanted revenge too! Hear how in a brand new Second Date podcast!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. 

One of our listeners tried to cover up an embarrassing moment by saying she had something in her teeth but what she was actually caught doing was way more embarrassing than that!See omnystudio.com/listener for privacy information. 

Today we visit two tales of out-of-place characters, and the legacy they've left behind.Join our Patreon for ad-free episodes!: https://www.patreon.com/grimandmildSee omnystudio.com/listener for privacy information. 

See omnystudio.com/listener for privacy information.