Brooke and Jeffrey: Second Date Update

See omnystudio.com/listener for privacy information.

One of our listeners BROKE UP with a guy and now she’s thinking she made a mistake. She wants him back but before she can get to him she’ll have to go through his SISTER in your Awkward Thursday Phone Call!See omnystudio.com/listener for privacy information.

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 find out why she left it and why she’s not calling him back!See omnystudio.com/listener for privacy information.

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 Tuesday Phone Call!See omnystudio.com/listener for privacy information.

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/listener for privacy information.

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, July 8th, 2026 Curious if we look as bad as we sound? Follow us @BrookeandJeffrey: Youtube Instagram TikTok BrookeandJeffrey.comSee omnystudio.com/listener for privacy information.

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 different because he finally executed the perfect date night...at least for a few minutes. We'll find out what went wrong this time! Part 2 Tara says MATH of all things helped her meet the perfect guy… You can hear how in your Second Date Update!See omnystudio.com/listener for privacy information.

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 you’ve never heard of this date idea before!See omnystudio.com/listener for privacy information.

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 they last talked with us. It’s a special Second Date Update UPDATE!See omnystudio.com/listener for privacy information.

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 went sideways SOMEHOW. See omnystudio.com/listener for privacy information.

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 sister of one of our listeners and we can’t believe what happened when he called to apologize to her!See omnystudio.com/listener for privacy information.

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 podcast!See omnystudio.com/listener for privacy information.

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, July 3rd, 2026 Curious if we look as bad as we sound? Follow us @BrookeandJeffrey: Youtube Instagram TikTok BrookeandJeffrey.comSee omnystudio.com/listener for privacy information.

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 life?  Part 2 In today’s Second Date Update there was one moment that brought the evening to a SCREECHING HALT!See omnystudio.com/listener for privacy information.

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 find out in your Second Date Update!See omnystudio.com/listener for privacy information.

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!"See omnystudio.com/listener for privacy information.

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 MIDDLE of a date.See omnystudio.com/listener for privacy information.

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.com/listener for privacy information.

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 what happened in a Second Date podcast!See omnystudio.com/listener for privacy information.

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, June 24th, 2026 Curious if we look as bad as we sound? Follow us @BrookeandJeffrey: Youtube Instagram TikTok BrookeandJeffrey.comSee omnystudio.com/listener for privacy information.

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 someone messed up your coffee order, would you politely let them know or go scorched-earth instead? It happened to one of our listeners and their response got the attention of the entire room!See omnystudio.com/listener for privacy information.

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 Update!See omnystudio.com/listener for privacy information.

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?See omnystudio.com/listener for privacy information.

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 figuring out just HOW FAR one man will go for just one, single date. See omnystudio.com/listener for privacy information.

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 in your Awkward Tuesday Phone Call!See omnystudio.com/listener for privacy information.

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 changed everything with one simple sentence! See omnystudio.com/listener for privacy information.

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: Thursday, June 18th, 2026 Curious if we look as bad as we sound? Follow us @BrookeandJeffrey: Youtube Instagram TikTok BrookeandJeffrey.comSee omnystudio.com/listener for privacy information.

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 judgment to go after him anyway! Part 2 Samantha 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.See omnystudio.com/listener for privacy information.

One of our listeners got maybe the worst possible response to an unsolicited text message… EVER!See omnystudio.com/listener for privacy information.

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.

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.

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.

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.

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 InstagramTikTok BrookeandJeffrey.comSee omnystudio.com/listener for privacy information.

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.

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.

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.

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.

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.

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.

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 InstagramTikTok BrookeandJeffrey.comSee omnystudio.com/listener for privacy information.

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.

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.

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.

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.

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.

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.

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 InstagramTikTok BrookeandJeffrey.comSee omnystudio.com/listener for privacy information.

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.

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.