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: Case of the Solo Shoe
We have a real-life Cinderella story on our hands today! Will has one of Teri’s SHOES after their night out and in your Second Date Update we’re gonna...
Awkward Tuesday: JFK & Oprah the Assassin
Stacy wants to explain how her romantic hangout nearly turned into a CRIME SCENE… and why her neighbor is now blaming HER for it, in your Awkward Tues...
Second Date Update: Car Wash Crush
One of our listeners says she found an UNDERRATED place for ladies to meet QUALITY guys… and it might shock you where.
See omnystudio.com/liste...
FULL SHOW: Voice Note Ick Date, Alexis Personal Love Island + Jeff’s New Beef (7/8/26)
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...
Second Date Update Classics: Randall Is Back + Highs & Lowells Of Dating
Part 1
After many failed romantic encounters and a couple of outright scams, one of our most lovable listeners is back! He says this time is dif...
Second Date Update: Anti-Farmers Market
Sam took Jamie to a UNIQUE first date spot. In fact, it was so unique, its not only impressive but it became it’s own conversation piece. We guarantee...
Second Date Update UPDATE: He Bought Me A Star
We’re bringing back a HIGHLY REQUESTED couple that have been on our show before, to get all the out-of-this-world details of what’s happened since the...
Second Date Update: Voice Note No No
Corey THOUGHT he had the perfect conversation starter but after he brought it up his date was in TEARS. He swears it was a harmless topic that just we...
Awkward Tuesday: 40th Birthday Blunder
The woman we call in today’s Awkward Tuesday Phone Call might be the most brutal, ruthless, and vile person we’ve ever had on the show. She’s the sist...
Second Date Update: Tap It or Scratch It
Andre managed to cancel plans on Kim NOT ONCE, but TWICE in the same night. Is that too much to come back from? Find out in your Second Date Update po...
FULL SHOW: Undercover Spy Date, Riffin’ Around Summer Edition + Pettiest Neighbors (7/3/26)
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...
Second Date Update Classics: B Dub Flub + Red Light Green Light
Part 1
When the woman on the phone today described her job to us we were SHOCKED… but is it something that would keep her from a happy dating li...
Second Date Update: I Brought My Mom
What the couple on the phone today went through on their date was JUST SHORT of the plot of a James Bond movie. Were they shaken or stirred? We’ll fin...
Say Yes To The Ex: Trio Tangle
We’re doing our best to reunite a listener with one of their previous romances… only if we don’t screw it up first. Catch a “Say Yes To The Ex!"
...
Second Date Update Classic: Uber Meets
One of our listeners says HER MOM may have accidentally ruined her chance with a guy and its all because of what mom needed from her daughter in the M...
Awkward Tuesday: Un-Dump My Ex
One of our listeners admits she might have taken things too far with her boyfriend, and now she wants our help to UN-dump him.
See omnystudio.co...
Second Date Update Classic: Dine For One But I'm Not Done
The listener on the phone says her date ended up with some unexpected extra guests… but it’s actually kind of sweet how it all came together. Hear wha...
FULL SHOW: Pursue Me Date, Alexis’ Identity Theft + Jeff’s Mom’s Song of the Week? (6/24/26)
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...
Second Date Update Classics: A Slip Of The Ex + Putting Together The Pieces
Part 1
One of our listeners claims they’ve discovered the GOLDEN pick-up line, hear what it is in your Second Date Update!
Part 2
If...
Second Date Update Classic: Not A Happy Camper
One of our listeners botched her date after trying to give him an honest compliment…. Hear how we tried to help her out her problem in a Second Date U...
Am I The Jerk? Save The Announcement
One of our listeners is soon to be married and she’s already made half her friends and family angry. Is she at fault or are they overreacting?
S...
Second Date Update: Pursue Me Please
Sometimes in the dating world, you have to decide if the pursuit is WORTH the prize at the end of the journey. In today’s Second Date Update we’re fig...
Awkward Tuesday: AI Messed Up
One of our listeners trusted his “idiot” friend to help cover for him, and now he could be out of an apartment AND a girlfriend. We’ll try to save him...
Second Date Update: Tamogatchi Tea
One of our listeners told us he was STRUGGLING to get his date back on track after a few early fumbles, until a COMPLETE STRANGER swooped in and chang...
FULL SHOW: Brooke Breaks You Up, Whatcha Doin’ at World Cup + Secret Man Crush (6/18/26)
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...
Second Date Update Classics: Failure To Launch + CSI Dinner Investigation
Part 1
Can a guys job be a red flag? The woman in today’s Second Date met her guy at his red flag job, and she decided against her better judgme...
Second Date Update Classic: I Dare You To Date Me
One of our listeners got maybe the worst possible response to an unsolicited text message… EVER!
See omnystudio.com/listener for privacy informa...
Brooke Breaks You Up: Drop the Stanford Dropout
It’s a favorite of the listeners and the bane of Brooke’s existence… We’re doing another edition of “BROOKE BREAKS YOU UP!”
See omnystudio.com/l...
Second Date Update: Stroll Club Hero
Josh tried to be funny to impress Lisa on their date and that plan BACKFIRED so badly, he found himself apologizing to a random 9 year old and his fam...
Awkward Tuesday: Paging Dr. Luke
We got BLINDSIDED by one of the BIGGEST LIES in the history of this show. It’s a complicated relationship problem and we’re doing our best to navigate...
Second Date Update: Shark Tanked
One of our listeners took his date to a ball game and INSTANTLY she was set off on a bad mood. He doesn’t know what sparked it but we’re on his side a...
FULL SHOW: Jeff’s World Cup Song, No Questions EVER Date + Dumbest Political Troll (6/12/26)
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...
Second Date Update Classics: Big Fragrance Energy + Trying To Connect 4
Part 1
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 U...
Second Date Update: No Questions Ever
One of our listeners has a SYSTEM to get a date with ANY woman you want. But some of his tactics were so controversial, it nearly BROKE Brooke!
...
Second Date Update UPDATE: First Base Fam
We’ve had “Momma’s boys” and women with “Daddy Issues” on our show before but today we’re reconnecting with a DIFFERENT type of Red Flag that involves...
Second Date Update: Too Pretty To Tip
Andrew overheard two woman saying something so SHOCKING & RUDE that he had to step in. He thinks he was heroic, but was it actually creepy?
See...
Awkward Tuesday: Surprise Surprise
A HUGE surprise is in total JEOPARDY and Olivia has turned to us for help! We’ll do our best to keep things on track in your Awkward Tuesday Phone Cal...
Second Date Update: Big Brain vs Semicolon Corey
One of our listeners says the woman he went out with wanted something VERY SPECIFIC whispered into her ears and it had him thinking “This woman is THE...
FULL SHOW: Jeff’s Class of ’26 Song, Ashton’s Parents vs Dating + Dead Flower Date (6/5/26)
Every Sunday, we host one of our FULL HOUR episodes from our main show feed, Brooke & Jeffrey! We'd love to hear your feedback...but please send all n...
Second Date Update Classics: Brunch Yuck + Down Under Blunder
Part 1
Rez DEFINITELY regrets a story he told Katrina on their date, and you’re gonna want to hear how he tells it in the Second Date Update!