Brooke and Jeffrey: Second Date Update

In your Awkward Tuesday Phone Call, one of our listeners is convinced her brother is hiding a big secret from the family, and she wants to reveal it with our help!See omnystudio.com/listener for privacy information.

Transcribed - Published: 23 December 2025

A quick trip to move his car ended up being a HUGE mistake for our listener, and it sent his date WILDLY OFF TRACK. Hear how it went down in a Second Date Update!See omnystudio.com/listener for privacy information.

Transcribed - Published: 22 December 2025

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, December 17th, 2025 Curious if we look as bad as we sound? Follow us @BrookeandJeffrey: Youtube Instagram TikTok BrookeandJeffrey.comSee omnystudio.com/listener for privacy information.

Transcribed - Published: 21 December 2025

Part 1 After we totally botched a Second Date for a guy a few months ago, he’s back and at this point we’re not sure if he’s trolling us or just likes the punishment. We can't let him down this time! Part 2 Imagine if you went on a date with a coworker and after the hang out, MULTIPLE PEOPLE are now avoiding you. It happened to one of our listeners and you can hear why in a Second Date!See omnystudio.com/listener for privacy information.

Transcribed - Published: 20 December 2025

One of our listeners turned a super awkward moment into an actual MEET CUTE that almost seemed TOO perfect. You’ll hear it in your Second Date Update podcast!See omnystudio.com/listener for privacy information.

Transcribed - Published: 19 December 2025

It’s one of the most controversial segments in the history of our show, but today it comes with a twist. It's the Holiday Edition of Brooke Breaks You Up!See omnystudio.com/listener for privacy information.

Transcribed - Published: 18 December 2025

The most annoying part of dating apps is all the wasted energy you put in, only to never actually meet up in person… But our listener on the phone says he has a method to eliminate that headache!See omnystudio.com/listener for privacy information.

Transcribed - Published: 17 December 2025

What if a family member overhears something they weren't supposed to, and now the holidays are going to be EXTRA WEIRD unless you make a phone call with our help? It's happening right here in your Awkward Tuesday Phone Call!See omnystudio.com/listener for privacy information.

Transcribed - Published: 16 December 2025

One of our listeners made her date laugh so hard that something embarrassing slipped out and she’s worried it’s the reason he’s not calling back!See omnystudio.com/listener for privacy information.

Transcribed - Published: 15 December 2025

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, December 10th, 2025 Curious if we look as bad as we sound? Follow us @BrookeandJeffrey: Youtube Instagram TikTok BrookeandJeffrey.com See omnystudio.com/listener for privacy information.

Transcribed - Published: 14 December 2025

Part 1 The guy on the phone today told us he’s fed up with being friend-zoned, and he wants to get ahead of things with a bizarre new plan we’ve never tried before!  Part 2 The guy on the phone says a random child walked up to their table during a romantic dinner and said something that threw off their ENTIRE EVENING. Is a kid really to blame for him not getting a Second Date?See omnystudio.com/listener for privacy information.

Transcribed - Published: 13 December 2025

One of our listeners made a BIG ASK, a request we never heard before… telling a guy if he wanted any shot at dating her, he had to do THIS first. Find out what it is in your Second Date Update podcast!See omnystudio.com/listener for privacy information.

Transcribed - Published: 12 December 2025

One of our listeners is having a problem dealing with her next door neighbor and it’s slowly ruining her life. We’ll try to help her with some Textual Healing!See omnystudio.com/listener for privacy information.

Transcribed - Published: 11 December 2025

One of our listeners says there's a sneaky spot where you can meet cute guys, and it ONLY happens during the holidays. You’ll find out where that is coming up in your Second Date Update podcast!See omnystudio.com/listener for privacy information.

Transcribed - Published: 10 December 2025

The woman on the phone today is ready to CONFRONT the person who has been scamming her for the past 3 years. It also happens to be her boyfriend…See omnystudio.com/listener for privacy information.

Transcribed - Published: 9 December 2025

It can be so difficult to find a guy who does the bare minimum, but the woman on the phone today found a guy who is OUT OF THIS WORLD! We’ll let her explain why she wants to see her date again, in your Second Date Update podcast!See omnystudio.com/listener for privacy information.

Transcribed - Published: 8 December 2025

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, December 3rd, 2025 Curious if we look as bad as we sound? Follow us @BrookeandJeffrey: Youtube Instagram TikTok BrookeandJeffrey.com See omnystudio.com/listener for privacy information.

Transcribed - Published: 7 December 2025

Part 1  One of our listeners met a guy in a peculiar way… by SAVING HIS LIFE! But why doesn’t he ever want to see her again? We’ll use a Second Date Update to find out. Part 2 The woman on the phone today was SHOCKED when she got a look inside her date's home and saw what he collects...Even though he swears it's for a good reason. Find out what it is in the podcast!See omnystudio.com/listener for privacy information.

Transcribed - Published: 6 December 2025

The guy on the phone today has HUGE regrets about asking his date about Ex...Yet he still wants our help getting in touch with her for a Second Date Update!See omnystudio.com/listener for privacy information.

Transcribed - Published: 5 December 2025

The couple on the phone today got the most AWKWARD comment a server could say to a table when they first appeared on our show a few months ago. Now, they’re BACK to give us a special Second Date Update UPDATE!See omnystudio.com/listener for privacy information.

Transcribed - Published: 4 December 2025

The woman on the phone today is CERTAIN that there is a logical explanation for why her date suddenly dropped off the face of the earth after ten days… We’re gonna help her KEEP HOPE ALIVE in your Second Date Update podcast! See omnystudio.com/listener for privacy information.

Transcribed - Published: 3 December 2025

Our listener says her boyfriend is TOO PERFECT, and it might be all her fault! It’s causing a problem that she wants to fix in a brand new Awkward Tuesday Phone Call!See omnystudio.com/listener for privacy information.

Transcribed - Published: 2 December 2025

One of our listeners wanted to sweep his date off her feet….. but based on the reactions we got in this room to his grand romantic gestures there’s a chance he MAY have overdone it… See for yourself in the Second Date Update podcast!See omnystudio.com/listener for privacy information.

Transcribed - Published: 1 December 2025

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: Monday, November 24th, 2025 Curious if we look as bad as we sound? Follow us @BrookeandJeffrey: Youtube Instagram TikTok BrookeandJeffrey.com See omnystudio.com/listener for privacy information.

Transcribed - Published: 30 November 2025

Part 1 One of our listeners said he changed ONE THING on his dating profile that instantly changed the game for him. He wishes he’d done this years ago and you can hear what it is in the Second Date podcast. Part 2  Out of every Second Date we’ve done this year, today's might be the most MEMORABLE of the bunch.See omnystudio.com/listener for privacy information.

Transcribed - Published: 29 November 2025

One of our listeners says he got his inspiration for his dating “MOVE” by watching on video online and gathering the courage to try it himself. Hear what it was in a Second Date podcast!See omnystudio.com/listener for privacy information.

Transcribed - Published: 28 November 2025

The holidays nearly broke up the couple on the phone today when they first dated a year ago. But now with the yuletide season coming up were going to reconnect with them for a special update!See omnystudio.com/listener for privacy information.

Transcribed - Published: 27 November 2025

The guy in today’s Second Date Update has been on the show before, but today he gets the special opportunity for a First Date REDATE!See omnystudio.com/listener for privacy information.

Transcribed - Published: 26 November 2025

Is it ever okay for a person to meddle in their friends love life? It doesn’t matter because we’re doing it anyway before one listener's friend can go on a blind date!See omnystudio.com/listener for privacy information.

Transcribed - Published: 25 November 2025

One of our listeners said he made a restaurant faux pas RIGHT AWAY on his date before he even put down the menu. We’ll talk to him and see if it derailed his chances in your Second Date Update!See omnystudio.com/listener for privacy information.

Transcribed - Published: 24 November 2025

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, November 21st, 2025 Curious if we look as bad as we sound? Follow us @BrookeandJeffrey: Youtube Instagram TikTok BrookeandJeffrey.com See omnystudio.com/listener for privacy information.

Transcribed - Published: 23 November 2025

Part 1  If you asked a million people if they thought the surprise one of our listeners had for the woman he was dating was a good idea, NOBODY would say “YES!” Part 2 One of our listeners is a barista and says she did something she would NEVER normally do… but taking that risk got her a date with a hot customer and now she wants our assistance bringing him back one more time!See omnystudio.com/listener for privacy information.

Transcribed - Published: 22 November 2025

Kevin’s unique hobby might be one of the weirdest things we’ve heard and we’re wondering if MAYBE it's reason he isn’t getting a call back...But it's also what makes him one of the most memorable listeners we've ever had on the show!See omnystudio.com/listener for privacy information.

Transcribed - Published: 21 November 2025

We're counting down our TEN FAVORITE Loser Line Clips of the entire year!See omnystudio.com/listener for privacy information.

Transcribed - Published: 20 November 2025

The woman on the phone today says she was FORCED to confront her biggest fear in the first 5 minutes of her date. We’ll figure out what she’s so scared of in your Second Date Update podcast!See omnystudio.com/listener for privacy information.

Transcribed - Published: 19 November 2025

In your Awkward Tuesday Phone Call, one of our listeners think his girlfriend’s new career path might be putting her in DANGER! We’ll sort it out and get down to the nitty gritty, in the podcast!See omnystudio.com/listener for privacy information.

Transcribed - Published: 18 November 2025

One of our listeners tried a dating HACK in today’s Second Date Update that guys might find useful, women probably hate it, and we’re just surprised it was even a THING!See omnystudio.com/listener for privacy information.

Transcribed - Published: 17 November 2025

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, November 12th, 2025 Curious if we look as bad as we sound? Follow us @BrookeandJeffrey: Youtube Instagram TikTok BrookeandJeffrey.comSee omnystudio.com/listener for privacy information.

Transcribed - Published: 16 November 2025

Part 1 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.  Part 2 One of our listeners swears he has a very good reason that’s totally “not sketch at all” for wanting to make sure his date location was EXTRA PRIVATE… We’re gonna hear him out in your Second Date Update.See omnystudio.com/listener for privacy information.

Transcribed - Published: 15 November 2025

The guy on the phone today says he left his date alone in his apartment and when he came back she was ready to BOLT away. We’re gonna try to figure out what spooked her in your Second Date Update podcast!See omnystudio.com/listener for privacy information.

Transcribed - Published: 14 November 2025

You're about to hear some drama between a brother and sister that's turning their Turkey Day into BERZERKY-DAY, and the only way we can help fix it, is with an Awkward Thursday Phone Call!See omnystudio.com/listener for privacy information.

Transcribed - Published: 13 November 2025

The only thing blocking Corey from finding love is TRUTH and HONEST. He might have told a little bit too much of the truth… Judge for yourself in the Second Date Update podcast!See omnystudio.com/listener for privacy information.

Transcribed - Published: 12 November 2025

The guy in today’s Awkward Tuesday Phone call is desperate to spark a romantic connection with someone he’s known for years. They’re not exactly friends… but they've been close for years...See omnystudio.com/listener for privacy information.

Transcribed - Published: 11 November 2025

We have a CONTROVERSIAL Second Date Update today where at some point during the date, somebody DEMANDED to speak to the restaurant manager. We’re in crisis mode in the podcast!See omnystudio.com/listener for privacy information.

Transcribed - Published: 10 November 2025

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, November 5th, 2025 Curious if we look as bad as we sound? Follow us @BrookeandJeffrey: Youtube Instagram TikTok BrookeandJeffrey.comSee omnystudio.com/listener for privacy information.

Transcribed - Published: 9 November 2025

Part 1 The guy on the phone today says his date night included a blindfold and a bit of deception, but it turned out even better than he ever planned. Hear what happened in your Second Date podcast. Part 2 The guy in today’s Second Date Update flew across the ocean just to meet someone he thinks MIGHT be the ONE!See omnystudio.com/listener for privacy information.

Transcribed - Published: 8 November 2025

Something was EXPELLED from the body of one of our listeners while on a date, and while it wasn’t gross, it did happen for over an hour....But it’s not dissuading our listener from trying to get a Second Date!See omnystudio.com/listener for privacy information.

Transcribed - Published: 7 November 2025

The couple on the phone today came on our show just a few short months ago, and their story was so captivating, we brought them back today for the first ever Awkward THURSDAY (UPDATE)!See omnystudio.com/listener for privacy information.

Transcribed - Published: 6 November 2025

One of our listeners is experimenting in a new dating strategy, all about the YEAR she was born. Find out what she’s doing in your Second Date Update podcast!See omnystudio.com/listener for privacy information.

Transcribed - Published: 5 November 2025

One of our listeners wants to find out the TRUTH of what happened when his girlfriend went on a GIRLS TRIP out of town… We’ll do our best to help in a new Awkward Tuesday Phone Call!See omnystudio.com/listener for privacy information.

Transcribed - Published: 4 November 2025