Brooke and Jeffrey: Second Date Update

The woman on the phone today DEEPLY regrets the compliment she paid to a guy, he took it the WRONG WAY and now Jose and Brooke are gonna have to dig deep for some advice in your Awkward Tuesday Phone Call podcast! See omnystudio.com/listener for privacy information.

What’s the boldest move a woman can make on the first date? Our listener on the phone today fears she might have pushed it in her interaction but we’re ready to help her get a Second Date Update! See omnystudio.com/listener for privacy information.

We're trying out a new idea for our fans of the 2nd Date Update! Every Sunday, we will be hosting 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, March 27th, 2026 Curious if we look as bad as we sound? Follow us @BrookeandJeffrey: Youtube Instagram TikTok BrookeandJeff...

Part 1 One of our listeners had women FLOCKING to him thanks to one subtle change to his wardrobe. Hear what it was in your Second Date Update. Part 2 When a listener describes his date as an "unconventional beauty", we're going to try to uncover if that's the reason she isn't calling him back! See omnystudio.com/listener for privacy information.

You’re gonna be shocked when you hear how BRIEF the conversation was that brought our listeners date to a COMPLETE and INSTANT STOP. Avoid this sentence if you can, once you hear it, in your Second Date Update podcast! See omnystudio.com/listener for privacy information.

One of our listeners ended up on a 10-hour long marathon first date and the only thing more shocking than that... is what happened after we hung up the phone! It’s a Second Date Update UPDATE! See omnystudio.com/listener for privacy information.

Our listener wasn’t TRYING to find a romantic connection, it was her 7 year old DAUGHTER who wanted to do it for her. Hear how a sneaky 2nd grader introduced MOMMY to an eligible bachelor in your Second Date Update podcast!  See omnystudio.com/listener for privacy information.

Lyndsey heard what romantic gesture her boyfriend of 4 months was trying to pull off for her and she is ADAMANT that we help her STOP HIM at ALL COSTS!  See omnystudio.com/listener for privacy information.

The woman on the phone today says not only was her date a “solid 9” but the date he planned for them put him head and shoulders above the rest! So why isn’t he calling her back? Find out in the Second Date Update podcast! See omnystudio.com/listener for privacy information.

We're trying out a new idea for our fans of the 2nd Date Update! Every Sunday, we will be hosting 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, March 18th, 2026 Curious if we look as bad as we sound? Follow us @BrookeandJeffrey: Youtube Instagram TikTok BrookeandJ...

Part 1 How can you parlay one night of fun with a person you met at the club into something more meaningful? We're going to help one of our listeners try to do exactly that. Part 2 One of our listeners got their 15 seconds of fame DURING A DATE and it included tv cameras recording EVERYTHING he said… See omnystudio.com/listener for privacy information.

James came on our show a few months ago and actually USED his previous experience to change for the better?? Hear how he’s worked to become a better DATER in your Second Date Update podcast! See omnystudio.com/listener for privacy information.

After “Brooke Breaks You Up” was such a controversial, but rousing success, we’re trying a NEW segment for the first time ever today... See omnystudio.com/listener for privacy information.

One of our listeners REGRETS being honest about his favorite hobby… he knows it can be a red flag for some women and he’s hoping we can help smooth it over in your Second Date Update podcast! See omnystudio.com/listener for privacy information.

One of our listeners managed to ruin a LONG TIME friendship with ONE single sentence… He’s ready to risk anything to take it back so we’re setting him up with an Awkward Tuesday Phone Call! See omnystudio.com/listener for privacy information.

Our listener says his date got totally derailed by an anonymous stranger and if he doesn’t find out WHO the veiled figure is, he may never get another shot to take Mysty to dinner!  See omnystudio.com/listener for privacy information.

Part 1 The guy on the phone today claims his date said one specific thing to their waiter that wasn't just a green flag...but made him instantly realize she was relationship material! Part 2 One of our listeners THOUGHT he had a second chance all lined up with his date, but a single one-word text message brought that reality crashing down.  See omnystudio.com/listener for privacy information.

One of our listeners ended up in the bathroom alongside her date and NOT in a good way… You’ll hear why she had no choice but to bring him with her in a Second Date Update! See omnystudio.com/listener for privacy information.

One of our listeners wants to make a BIG MOVE with a woman he’s known for 6 DAYS. You’ll hear it, and why he needs our help pulling it off with some Textual Healing! See omnystudio.com/listener for privacy information.

One of our listeners found the ULTIMATE HACK to take a woman out, without breaking the bank. It requires a tad bit of deception though… find out more in your Second Date Update podcast! See omnystudio.com/listener for privacy information.

Today’s Awkward Tuesday Phone Call involves a private plane, a nervous pet, and one BIG question that our listener needs help asking. See omnystudio.com/listener for privacy information.

The guy looking to score another hangout with date isn’t even on the phone with us! Someone else is doing the call IN HIS PLACE! Find out who it is in your Second Date Update! See omnystudio.com/listener for privacy information.

We're trying out a new idea for our fans of the 2nd Date Update! Every Sunday, we will be hosting 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, March 6th, 2026 Curious if we look as bad as we sound? Follow us @BrookeandJeffrey: Youtube Instagram TikTok BrookeandJeffr...

Part 1 The guy on the phone for today’s Second Date Update says we need to get him ANSWERS, not just for his sanity, but for his FRIEND GROUP who played a strange role in his date. Part 2 One of our female listeners used an innocent little excuse…. To go from awkward end of the night hug… to Instant sleepover at his place… Your gonna hear how she did it! See omnystudio.c...

One of our listeners was MORTIFIED when her date accidentally saw something that was NEVER intended for his eyes… She needs our help with a Second Date Update!  See omnystudio.com/listener for privacy information.