
Brooke and Jeffrey: Second Date Update
2,129 episodes — Page 7 of 43

Second Date Update: Escape the Fridgescape
One of our listeners got a woman to come home with him thanks to a unique skill that was so bizarre it had Brooke asking for PICS!See omnystudio.com/listener for privacy information.

Second Date Update Classics: Hoping For A Bad Date + Nathan Of The Night
Part 1 A beautiful woman asked one of our listeners to take her out on a date… to a place she HATES! Why would she want that? We’ll get her to come clean in your Second Date Update. Part 2 The entire show was very surprised by how today’s Second Date finished. And we think all our listeners will agree… it was Brooke’s fault.See omnystudio.com/listener for privacy information.

Second Date Update: Him At The Gym
One of our listeners tried out a dating LIFE HACK and it worked for her first try! Could it work for you too? Find out what it is in your Second Date Update.See omnystudio.com/listener for privacy information.

Say Yes To The Ex: Guys and Girls Trip
This segment might be one of our most difficult tasks we’ve faced this entire year! It’s an all new “SAY YES TO THE EX” and boy, is our work cut out for us!See omnystudio.com/listener for privacy information.

Second Date Update: CSI Dinner Investigation
One of our listeners warned her date that there’s ONE THING he HAD to do before she would see him… and he was shocked to find out she was SERIOUS. Hear what it was in a new Second Date Update podcast!See omnystudio.com/listener for privacy information.

Awkward Tuesday: Prenup or Pre-NOPE
One of our listeners has a looming conversation coming up and it’s one of the most difficult things you could ever talk about with a loved one. Before it happens they want our help via an Awkward Tuesday Phone Call!See omnystudio.com/listener for privacy information.

Second Date Update: Big Fragrance Energy
One of our listeners is worried her gratitude for a gift was BADLY misinterpreted as rude and now she wants our help with a Second Date Update!See omnystudio.com/listener for privacy information.

Second Date Update Classics: Love Is On the House + Started From The DM’s
Part 1 One of our listeners described their dinner date as the most IMPRESSIVE thing that they had ever seen. We HAD to know more so we contacted them as part of today Second Date Update. Part 2 One of our listeners admits he struggled to keep his cool on his date once he saw something on her Instagram. We couldn't believe it when we heard it either!See omnystudio.com/listener for privacy information.

Second Date Update: Brunch Yuck
One of our listeners DEFINITELY regrets a story he told on his date, and you’re gonna want to hear how he tells it in the Second Date Update podcast!See omnystudio.com/listener for privacy information.

Closure Call: Grandpa's Inheritance
If you had to choose, would you pick your family or a life-changing amount of money? A listener was faced with that choice and today he’s discussing his decision on our show in a Closure Call!See omnystudio.com/listener for privacy information.

Second Date Update: Best Date of My Life
The kiss that happened at the end of our listener's date was either the cutest, most spontaneous thing ever, or the cringiest, most awkward interaction of all time. Decide for yourself after the new Second Date Update!See omnystudio.com/listener for privacy information.

Awkward Tuesday: Graduating Class of 2025
For one of our listeners, there’s ONE MAJOR THING standing in the way of the perfect graduation party for her son… and that’s her neighbor.See omnystudio.com/listener for privacy information.

Second Date Update: Doodle Worthy
One of our listeners tried a UNIQUE STRATEGY to extend his date.… and even he admits, it was WAY more cringe than he thought it would be… You’ll hear what happened in your brand new 2nd date update podcast!See omnystudio.com/listener for privacy information.

Blind Love Is? Reunion of Love
We've got a special new episode you this weekend! We’ve got two hopeful singles, ready to meet for the FIRST TIME on our show… and Brooke’s glasses are already on PRE-FOG…. In anticipation of BLIND LOVE IS!See omnystudio.com/listener for privacy information.

Second Date Update Classics: Vacation Date Gone Wrong + Old Flame New Burn
Part 1 Brooke has seen a lot in her 400 years in radio, but today one of our listeners put her in the most DRAMATIC and UNCOMFORTABLE situation of her entire career. Part 2 There’s some topics you just don’t bring up on a first date. One of our listeners didn’t follow that rule and now it’s no surprise he needs our help in a brand new Second Date Update!See omnystudio.com/listener for privacy information.

Second Date Update: Two Word Whisperer
The woman on the phone today says her date decided to switch booths HALFWAY through their dinner… And all of us were stunned when we finally learned the actual reason he demanded to move locations...Hear for yourself in a brand new Second Date Update!See omnystudio.com/listener for privacy information.

Second Date Update UPDATE: Plant Me A Kiss
Two plant parents became one of our sweetest Second Date Update calls we’ve done all year, and even better we’ve got an update on their situation coming up in the podcast!See omnystudio.com/listener for privacy information.

Second Date Update: Flea Market Find
Our listener on the phone today says his date set a boundary before they even met in person. He had to say “yes,” to get a shot at her, and now we’re trying to get her to say “Yes” to a Second Date!See omnystudio.com/listener for privacy information.

Awkward Tuesday: I Want To Date My Friend's Ex
Is it ever okay to date your friends EX? Don’t ask us, in fact, just get ‘em on the phone for an Awkward Tuesday Phone Call instead!See omnystudio.com/listener for privacy information.

Second Date Update: Lonely Cannoli
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 brand new Second Date Update!See omnystudio.com/listener for privacy information.

Textual Healing: Ex-pectations
We've got a special new episode you this weekend! Normally on this show we try to HELP make a romantic connection but coming in today’s Textual Healing one listener wants us to make it clear she wants NOTHING to do with a guy that’s supposed to come over to her house later!See omnystudio.com/listener for privacy information.

Second Date Update Classics: 2nd Chance Scott + Mysterious Wallet Situation
Part 1 One of our listeners took a woman on a BEACH DATE and he gets huge props for one thing he DIDN’T DO… what was it? We're going to find out! Part 2 Today’s Second Date Update might involve one of the GREATEST SCAMS we’ve ever heard on a first date… Hear for yourself in the podcast!See omnystudio.com/listener for privacy information.

Second Date Update: 1st Impressions Are Everything
One of our listeners invited her date back to her place and spent HOURS together… but what she saw him do… she’s STILL trying to process. Hear what she went through in a new Second Date Update!See omnystudio.com/listener for privacy information.

Second Date Update: Meal Me Once
If you’re looking for a unique, innovative and new move to pick up women, you need to catch today’s Second Date Update with a guy who swears his tactic worked (at least ONCE).See omnystudio.com/listener for privacy information.

Awkward Tuesday: False Setto Freakout
One of our listeners is dealing with a difficult type of neighbor drama. You’re gonna want to hear our advice coming up in a brand new Awkward Tuesday Phone Call!See omnystudio.com/listener for privacy information.

Second Date Update: One Year Later To Rejection King
One of our listeners wishes she could take back what she said 11 months ago to a guy she went out with. It took her a year to realize her mistake, and now she wants another chance in a Second Date Update!See omnystudio.com/listener for privacy information.

Say Yes to the Ex: Unlucky Number 13
We've got a special new episode you this weekend! It’s easy to say yes to some things, but saying YES to your EX is another story… After today’s call you’re never gonna look at ESCAPE ROOMS the same again. It’s SAY YES TO THE EX!See omnystudio.com/listener for privacy information.

Second Date Update Classics: Picture Says It All + Promotion Commotion
Part 1: One of our listeners figured out a way to get his entire evening PAID FOR, and it involved no lying, not scheming and not cheating. How did it work? We're going to find out! Part 2: One of our listeners says it was a HUGE PLUS that his date listened to our show! That should have been his first red flag, now he wants our help in your Second Date Update. Get your 2nd Date Update Merch For A Cause HERE!See omnystudio.com/listener for privacy information.

Second Date Update: Yup Date for Jessica
A mysterious handwritten note was dropped onto the table during our listener's date and it altered both of their lives forever! Hear what it said coming up in a new Second Date Update! Get your 2nd Date Update Merch For A Cause HERE!See omnystudio.com/listener for privacy information.

Second Date Update: Three Wheelin' It
One of our listeners is confused after his date ended in the WEIRDEST way ever… but he still has SOME interest, so it couldn’t be that bad. Hear the brand new Second Date Update in the podcast! Get your 2nd Date Update Merch For A Cause HERE! See omnystudio.com/listener for privacy information.

Awkward Tuesday: Birthday Scamazon
One of our listeners was SHOCKED by the children’s birthday invite her son received… in fact, all the parents were so bothered by the strange instructions, she needs our help with an Awkward Tuesday Phone Call!See omnystudio.com/listener for privacy information.

Second Date Update Classic: The Blame Game
In the podcast you can hear the SHOCKING and UNFORTUNATE events that happened during our Second Date Update – and they were all totally Brooke’s fault! Get your 2nd Date Update Merch For A Cause HERE!See omnystudio.com/listener for privacy information.

True Confessions: School Edition
We've got a special new episode you this weekend! Can you figure out which of these embarrassing stories from our high school days are true and which ones are lies? It’s TRUE CONFESSIONS!See omnystudio.com/listener for privacy information.

Second Date Update Classic: Scam the Scammer
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.

Second Date Update: First Date Demise
We guarantee once you hear today’s Second Date Update that you’ll be cheering for single school teacher Marianne to find her true love! Get your 2nd Date Update Merch For A Cause HERE!See omnystudio.com/listener for privacy information.

Second Date Update: Hang Up On Him
One of our listener’s first kiss happened but her second date never did! So we’re gonna do everything in our power to get to the bottom of it in a brand new Second Date Update! Get your 2nd Date Update Merch For A Cause HERE!See omnystudio.com/listener for privacy information.

Awkward Tuesday: Sharing Aaron
One of our listeners came across an overbearing mother and what went down between them is either gonna be the biggest misunderstanding ever, or the most awkward roommate convo of her life!See omnystudio.com/listener for privacy information.

Second Date Update: Unconventional Beauty and the Feast
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.

Textual Healing: Peek A Boo Your Neighbor Can See You
We've got a special new episode you this weekend! One of our listeners caught his neighbor doing something that's making him very uncomfortable... it's happened MULTIPLE times and he feels like he's gotta say something... but he can't do it in person so we had him on for some Textual Healing!See omnystudio.com/listener for privacy information.

Second Date Update Classic: The Birthday Trick
One of our listeners managed to make a genuine connection with a woman, all because of one trick he’s been using for YEARS! Hear what it is in your Second Date Update podcast! Get your 2nd Date Update Merch For A Cause HERE!See omnystudio.com/listener for privacy information.

Second Date Update: The Ride Of Shame
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 in a brand new Second Date Update! Get your 2nd Date Update Merch For A Cause HERE!See omnystudio.com/listener for privacy information.

Second Date Update UPDATE: Bumpin' Carts
Today is proof that just because we think a relationship is doomed doesn't mean anything... because one of the most unexpected couples we've had on our show are BACK for a Second Date Update UPDATE! Get your 2nd Date Update Merch For A Cause HERE!See omnystudio.com/listener for privacy information.

Second Date Update: The First Five Seconds
When you're out to dinner and you notice something on your date's face, do you tell them or keep it to yourself? One of our listeners is worried the choice he made is why he's not getting a call back. We'll find out in a brand new Second Date Update! Get your 2nd Date Update Merch For A Cause HERE!See omnystudio.com/listener for privacy information.

Awkward Tuesday: Guy In A Tree
One of our listeners met a guy at a house party and says he literally RISKED HIS LIFE to not get caught with her! Now she wants answers! We're going to help her in a brand new Awkward Tuesday phone call!See omnystudio.com/listener for privacy information.

Second Date Update: Flirt and Observe
One of our listeners says she experienced an intimate moment with a guy she’d never met, when they were in a crowded coffee shop at the same time… and It was definitely more than just flirty eye contact. We're going to hear how that transpired into a whole afternoon together in your brand new Second Date Update! Get your 2nd Date Update Merch For A Cause HERE!See omnystudio.com/listener for privacy information.

Say Yes To The Ex: Podcast Problems
We've got a special new episode you this weekend! One of our listeners got dumped a few months ago during an argument about TOENAILS... But now, he swears he's changed and can PROVE IT. We've got his ex- girlfriend on the phone in hopes to get him another chance in a brand new Say Yes to the Ex!See omnystudio.com/listener for privacy information.

Second Date Update Classic: Red Envelope Regret
If only finding a date was as easy as ordering your favorite drink. One of our listeners had the perfect girl right in front of him all thanks to a new dating event that even YOU might want to try! Get your 2nd Date Update Merch For A Cause HERE!See omnystudio.com/listener for privacy information.

Second Date Update: A Picture Says A Thousand Icks
Our listener 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! You’ll hear what it was in your brand new Second Date Update! Get your 2nd Date Update Merch For A Cause HERE!See omnystudio.com/listener for privacy information.

Second Date Update: Date Night Veto
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 it in your brand new Second Date Update podcast! Get your 2nd Date Update Merch For A Cause HERE!See omnystudio.com/listener for privacy information.

Awkward Tuesday: Cheating Across Continents
One of our listeners is facing a huge moral dilemma, does she mind her own business, or possibly ruin her friends relationship?See omnystudio.com/listener for privacy information.