Awkward Tuesday: A Rabbi Walks Into A Bar

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 @BrookeandJeffrey: YouTube Instagram TikTok BrookeandJeffrey.comSee omnystudio.com/listener for privacy information.

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 sneaking suspicion it might be a trap but only one way to find out!See omnystudio.com/listener for privacy information.

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.

You may remember Brian and Olivia as a “Disney DO & Disney DON’T” couple where he was super into all things Disney and she was open to learning more…. But where are they now MONTHS after they first appeared on the show? Find out in your Second Date Update UPDATE!See omnystudio.com/listener for privacy information.

What’s the most embarrassing thing your date could catch you doing? David got caught at a bad time RIGHT as his date was meeting up with him and it happened AGAIN later on. We’ll help him try to recover in your Second Date Update podcast!See omnystudio.com/listener for privacy information.

Meeting your girlfriend’s parents can be stressful! It happened to Simon over a month ago, so why NOW does he need our help “fixing” what he says went wrong? Find out in a new Awkward Tuesday Phone Call!See omnystudio.com/listener for privacy information.

In today’s Second Date Update we found ourselves in the middle of a problem that is WAY out of our price range, even Brooke’s! 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: Thursday, October 8th, 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 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 that he’s been rejected by a woman! 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.