Brooke and Jeffrey: Second Date Update
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Brooke and Jeffrey: Second Date Update
Ghosted after a first date? We call the person who isn't calling you back to find out the real reason why and get you a Second Date. Low success rate...high entertainment for the rest of us. Want more? Catch the FULL hour long show over at Brooke and Jeffrey: iHeartRadio: https://www.iheart.com/podc...
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Second Date Update Classics: The Boy Who Cried Tree + Deck The Mall
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...
#7 Second Date Update of 2025: Street Walker Love Story
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...
Brooke Breaks You Up: Holiday Edition
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...
#8 Second Date Update of 2025: That Name Sounds Familiar
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 say...
Awkward Tuesday: Baby Monitor Drama
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 wi...
#9 Second Date Update of 2025: Dragon Thumbs & Aroma Chums
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!
FULL SHOW: Holiday Men Hack Date, Jose’s Midnight Meet Up + Smaller is Better for Jeff (12/10/25)
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 fee...
Second Date Update Classics: 3rd Times a Yawn + Super Kid Shames the Day
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...
#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...
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...
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 c...
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…
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 e...
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 fee...
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...
Second Date Update Podcast: 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 U...
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, t...
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...
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 Tue...
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...
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 fee...
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 ye...
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 w...
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...
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 omnyst...
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...
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 derai...
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 fee...
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...
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...
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.
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 scare...
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...
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 i...
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 fee...
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 pr...
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 ou...
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, i...
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...
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 frien...