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 information.
Jun 19, 2026•19 min
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/podcast/1119-brooke-and-jeffrey-110194157/
Apple: https://podcasts.apple.com/us/podcast/brooke-and-jeffrey/id1252608081
Spotify: https://open.spotify.com/show/6wmqpNulHEqJNeR2iqmgyj?si=6cdcc5432d75423f
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Episodes
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/listener for privacy information.
Jun 18, 2026•19 min
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 family. Hear how his humor got him in trouble in your Second Date Update podcast! See omnystudio.com/listener for privacy information.
Jun 17, 2026•18 min
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 it in your Awkward Tuesday Phone Call! See omnystudio.com/listener for privacy information.
Jun 16, 2026•18 min
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 and we’re gonna dig in, when we do a Second Date Update! See omnystudio.com/listener for privacy information.
Jun 15, 2026•18 min
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 send all negative reviews to Jeffrey. FULL SHOW: Friday, June 12th, 2026 Curious if we look as bad as we sound? Follow us @BrookeandJeffrey: Youtube Instagram TikTok BrookeandJeffrey.com See omnystudio.com/listener for privacy information....
Jun 14, 2026•1 hr 5 min
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 Update! Part 2 What do you do when someone suddenly STOPS replying to your texts? One of our listeners did something a little UNUSUAL to get his crush’s attention. See omnystudio.com/listener for privacy information.
Jun 13, 2026•37 min
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! See omnystudio.com/listener for privacy information.
Jun 12, 2026•18 min
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 a third type of family member… It’s a special Second Date Update UPDATE where if you listen until the end we check in with the couple and how things have gone since they first appeared on our show! See omnystudio.com/listener for privacy information.
Jun 11, 2026•18 min
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 omnystudio.com/listener for privacy information.
Jun 10, 2026•17 min
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 Call! See omnystudio.com/listener for privacy information.
Jun 09, 2026•19 min
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 ONE!” Find out what that was coming up in your Second Date Update podcast! See omnystudio.com/listener for privacy information.
Jun 08, 2026•19 min
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 negative reviews to Jeffrey. FULL SHOW: Friday, June 5th, 2026 Curious if we look as bad as we sound? Follow us @BrookeandJeffrey: Youtube Instagram TikTok BrookeandJeffrey.com See omnystudio.com/listener for privacy information....
Jun 07, 2026•1 hr 4 min
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! Part 2 One of our listeners is looking for all the help he can get locking down another hang out with a VERY classy woman. See omnystudio.com/listener for privacy information.
Jun 06, 2026•37 min
Second Date Update: Three Day Bouquet
Is a gift ever okay on the first date? Does it say too much or go too far? We go to the bottom of that question and got way more than we bargained for in your Second Date Update podcast! See omnystudio.com/listener for privacy information.
Jun 05, 2026•18 min
Textual Healing: Breakup Breakfast
Maria is caught in a complicated entanglement of the modern dating scene and she wants our help to UNCOMPLICATE it in the weirdest way possible. It's your Textual Healing Podcast! See omnystudio.com/listener for privacy information.
Jun 04, 2026•20 min
Second Date Update: Capes At Costco
We’ve heard some strange dealbreakers before on this show, but NOTHING has us as confused as the dealbreaker Kai had for Amy in today’s Second Date Update! See omnystudio.com/listener for privacy information.
Jun 03, 2026•19 min
Awkward Tuesday: Ship My Situationship
Our listener, Juliana, let something slip at the WRONG moment and now she wants our help getting her situationship back on track! We’ll do our best in the Awkward Tuesday Phone Call! See omnystudio.com/listener for privacy information.
Jun 02, 2026•19 min
Second Date Update: Door Dash Ashley
Blake didn’t spend ANY money on his date with Ashley, in fact, he actually MADE money in a way that’s 100% legal. You’ll hear how in your Second Date Update podcast! See omnystudio.com/listener for privacy information.
Jun 01, 2026•19 min
FULL SHOW: Jeffrey’s 1,000th Song, Ashton’s Move Back Home + Divorce Party Date (5/29/26)
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 send all negative reviews to Jeffrey. FULL SHOW: Friday, May 29th, 2026 Curious if we look as bad as we sound? Follow us @BrookeandJeffrey: Youtube Instagram TikTok BrookeandJeffrey.com See omnystudio.com/listener for privacy information....
May 31, 2026•1 hr 4 min
Second Date Update Classics: No Fire In The Fireplace +Best Date Of My Life
Part 1 One of our listeners realized she’s been approaching dating apps the wrong way… and one piece of advice completed shifted her romantic life. Part 2 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 Second Date Update! See omnystudio.com/listener for privacy information....
May 30, 2026•38 min
Second Date Update: Can't Beat The Sweet Treat
One of our listeners showed up to his co-workers “DIVORCE PARTY” and while the theme was a bit strange, the romance levels were surprisingly high and now we’re gonna help him get ahold of the woman he met there in your Second Date Update! See omnystudio.com/listener for privacy information.
May 29, 2026•17 min
Second Date Update UPDATE: Euro Date
Two of our listeners told us about “European Dating” and it led to one of the most popular Second Date Updates of the year! Now, they’re back on again for a special UPDATE UPDATE! See omnystudio.com/listener for privacy information.
May 28, 2026•19 min
Second Date Update: Defensive Driving Drama
Jay let Allie know IMMEDIATELY what ONE THING has been a deal breaker, about his past… He thought she would appreciate it, but now he’s asking us for a Second Date Update! See omnystudio.com/listener for privacy information.
May 27, 2026•18 min
Awkward Tuesday: Party Hard Granny
One of our listeners told us her grandma is getting KICKED OUT of her senior home. It’s a unique circumstance and now she wants our help with an Awkward Tuesday Phone Call! See omnystudio.com/listener for privacy information.
May 26, 2026•18 min
Second Date Update Classic: Senior Moment Slip Up
One of our listeners admits she broke more than FIVE unwritten rules of dating, but she says she had a good reason too! See omnystudio.com/listener for privacy information.
May 25, 2026•18 min
FULL SHOW: Mistaken Identity Date, Paid Wedding Crashers + First Bidet Loser Line (5/18/26)
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 send all negative reviews to Jeffrey. FULL SHOW: Monday, May 18th, 2026 Curious if we look as bad as we sound? Follow us @BrookeandJeffrey: Youtube Instagram TikTok BrookeandJeffrey.com See omnystudio.com/listener for privacy information....
May 24, 2026•1 hr 5 min
Second Date Update Classics: Update My Dino Profile + Doodle Worthy
Part 1 One of our listeners went down a weird internet rabbit hole and what she found changed her whole approach to dating… Hear what she learned in your Second Date Update! Part 2 The guy on the phone today tried a UNIQUE STRATEGY to extend his date.… and even he admits, it was WAY more cringe than he thought it would be… See omnystudio.com/listener for privacy information.
May 23, 2026•38 min
Second Date Update Classic: Train Game
There’s no EASY way to approach an attractive person on public transportation, and that was exactly the case for our listener! She’ll tell us her story and how she wants to get in touch with a guy she met on the train coming up in a Second Date Update! See omnystudio.com/listener for privacy information.
May 22, 2026•18 min
Awkward Thursday: 30 Day Girlfriend
Normally, we help people get second dates after a first one, but today we’re helping a guy who hasn’t even had ONE date with the woman he’s interested, and he wants to jump straight into a relationship! See omnystudio.com/listener for privacy information.
May 21, 2026•19 min
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