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Brooke and Jeffrey: Second Date Update

Brooke and Jeffrey: Second Date Update

2,129 episodes — Page 4 of 43

#10 Second Date Update of 2025: Give Him The Golden

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.

Dec 12, 202518 min

Textual Healing: Dog Disturbance

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.

Dec 11, 202518 min

Second Date Update: Does This Smell Like Your Mom?

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.

Dec 10, 202518 min

Awkward Tuesday: Knock Off No No

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.

Dec 9, 202518 min

Second Date Update: He Bought Me A Star

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.

Dec 8, 202517 min

FULL SHOW: The Last Hopeful Dater, Jeff’s Mom’s High Speed Chase & Alexis’ Car Casino (12/3/25)

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.

Dec 7, 20251h 6m

Second Date Update Classics: Double Roasted Turkey + 20 Treadmills of Love

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.

Dec 6, 202537 min

Second Date Update: Never Ask About The Ex

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.

Dec 5, 202518 min

Second Date Update UPDATE: Age Is Just A Bummer

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.

Dec 4, 202518 min

Second Date Update: Beer & Butterfly Kisses

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.

Dec 3, 202517 min

Awkward Tuesday: Change Him Back

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.

Dec 2, 202518 min

Second Date Update: Love Bombs Away

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.

Dec 1, 202518 min

FULL SHOW: Dinner Faux Pas Date, Riffin Around Food Edition + Daddy & Me Loser Line (11/24/25)

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.

Nov 30, 20251h 4m

Second Date Update Classics: Driving Miss Laurie + Lick My Neck

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.

Nov 29, 202536 min

Second Date Update Classic: Cutecumber Couple

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.

Nov 28, 202517 min

Second Date Update UPDATE Classic: 8 Trees A Trimming

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.

Nov 27, 202518 min

Second Date Update Classic: First Date Redate

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.

Nov 26, 202517 min

Awkward Tuesday: Stop That Ugly Duckling

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.

Nov 25, 202519 min

Second Date Update Classic: Red Flaggy Much?

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.

Nov 24, 202518 min

FULL SHOW: Jeff’s Iconic Thanksgiving Song, Turkey Day Mishaps + Late & Petty Date (11/21/25)

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.

Nov 23, 20251h 5m

Second Date Update Classics: Date Night Detour + Barista Foam Job

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.

Nov 22, 202537 min

Second Date Update: Microwave Mosaics

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.

Nov 21, 202519 min

Top 10 Loser Lines of 2025

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

Nov 20, 202518 min

Second Date Update: Escalator Escape

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.

Nov 19, 202517 min

Awkward Tuesday: Wanna Be A Cop

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.

Nov 18, 202518 min

Second Date Update: Bottom of the Bread Bowl

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.

Nov 17, 202518 min

FULL SHOW: The Only Match Date, Jeff’s Celebrity Man Crush + Jose’s $100 Soup (11/12/25)

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.

Nov 16, 20251h 8m

Second Date Update Classics: Strings of Deceit + Claus for Concern

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.

Nov 15, 202536 min

Second Date Update: Awkward Hugs & Hot Dogs

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.

Nov 14, 202517 min

Awkward Thursday: No Free Family Dinner

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.

Nov 13, 202518 min

Second Date Update: Corey's Crazy Criteria

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.

Nov 12, 202518 min

Awkward Tuesday: Nanny Zoned

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.

Nov 11, 202519 min

Second Date Update: Ditch Me No Ditch You

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.

Nov 10, 202518 min

FULL SHOW: 30 for 30 Challenge Date, Jeff Trapped at Work + Brooke’s Turkey Trouble (11/5/25)

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.

Nov 9, 20251h 8m

Second Date Update Classics: Seafood Surprise + Philippines or Bust

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.

Nov 8, 202536 min

Second Date Update: Karaoke Cryer

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.

Nov 7, 202517 min

Awkward Thursday UPDATE: He Saw What He Saw

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.

Nov 6, 202518 min

Second Date Update: 30 for 30

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.

Nov 5, 202518 min

Awkward Tuesday: Girls Trip Mystery

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.

Nov 4, 202518 min

Second Date Update: Red Flag Test

We needed the listener on the phone today to be 100% HONEST about what happened with his date, and that proved to be harder than we realized…See omnystudio.com/listener for privacy information.

Nov 3, 202518 min

HALLOWEEN SHOW: Jeff’s Disney Villian Song, Boo’s & Booze Date + Ghost Hunter Prank (10/31/25)

We didn't want you to miss out on our favorite show of the year... Halloween is our Superbowl! Enjoy all the spooky crazy fun from our main show feed, Brooke & Jeffrey! FULL SHOW: Friday, October 31st, 2025 Curious if we look as bad as we sound? Follow us @BrookeandJeffrey: Youtube Instagram TikTok BrookeandJeffrey.comSee omnystudio.com/listener for privacy information.

Nov 2, 20251h 5m

Second Date Update Classics: It's A Costume Dummy + Blackout Drunk Shuttlecock

Part 1 The guy in today’s Second Date Update tried a pickup line that was cringey, not just on one level… but on MULTIPLE LEVELS and he quickly realized he needed our help. Part 2 One of our listeners found themselves in the middle of an epic house party and he thinks he found a girl he wants to get serious with… but something happened on the way over to the daiquiri mix… and we’re about to get to the bottom of it in your Second Date Update!See omnystudio.com/listener for privacy information.

Nov 1, 202536 min

Second Date Update: Halloween Boos and Booze Bar Crawl

One critical moment told the ENTIRE story of our listener's date and now they BOTH can’t stop talking about it. Hear how it went down in your Halloween Second Date Update podcast!See omnystudio.com/listener for privacy information.

Oct 31, 202518 min

Blind Love Is? Halloween Edition

Buckle up Boys and Ghouls, it's a special double-jam-packed HALLOWEEN EDITION of BLIND LOVE IS?See omnystudio.com/listener for privacy information.

Oct 30, 202518 min

Second Date Update: Halloween Bean Dip Mystery

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.

Oct 29, 202518 min

Awkward Tuesday: Dark Side of the Costume Contest

A new costume is causing MAJOR drama between a listener and his close friend, and he has no idea where else to turn! It’s a Halloween-themed Awkward Tuesday Phone Call!See omnystudio.com/listener for privacy information.

Oct 28, 202519 min

Second Date Update: Romeo and Ghouliet

The guy in today’s Second Date works at a haunted house and is looking to reconvene with a coworker he once dated. It’s Halloween week and we’re hoping to treat them both right in the podcast!See omnystudio.com/listener for privacy information.

Oct 27, 202517 min

FULL SHOW: Outed by Facebook Date, Nurse Alexis Fails + No Cake for Jeffrey (10/22/25)

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, October 22nd, 2025 Curious if we look as bad as we sound? Follow us @BrookeandJeffrey: Youtube Instagram TikTok BrookeandJeffrey.comSee omnystudio.com/listener for privacy information.

Oct 26, 20251h 7m

Second Date Update Classics: 10 Pin Mixup + Pop Goes the Relationship

Part 1How badly are you willing to embarrass yourself if it means getting a date with that special person? One of our listeners went to the limit LIVE ON AIR and you get to hear it!Part 2A listener on the phone today says his first kiss with his date left a LOT to be desired… and now he wants our help fixing their issue in a Second Date Update podcast.See omnystudio.com/listener for privacy information.

Oct 25, 202536 min

Second Date Update: Get That Sizzle

One of our listeners found his PERFECT MATCH and it wasn’t on one of the popular dating apps you’ve probably heard of. We’ll reveal which dating site you’re probably gonna want to sign up for in your Second Date Update podcast!See omnystudio.com/listener for privacy information.

Oct 24, 202518 min