Brooke and Jeffrey: Second Date Update

The guy on the phone for today’s Awkward Thursday Phone Call DESPERATELY needs our help because his HOA is threatening to FINE him hundreds of dollars if he goes through with his favorite Halloween tradition! See omnystudio.com/listener for privacy information.

One of our listeners has a crush on his co-worker and he came up with a plan to show her! It involves a microwave and a wilted bowl of salad…  See omnystudio.com/listener for privacy information.

Two weeks after tying the knot, Katherine wants an apology from one of her unruly family members for the way he acted at her wedding. Its your Awkward Tuesday Phone Call! See omnystudio.com/listener for privacy information.

Susan said her date asked her a STRANGE question at the end of the night and was VERY disappointed by her response… You’ll hear the question and her answer in your Second Date Update! 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, October 16th, 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.

Part 1 Nick is willing to tell us the MOST EMBARRASSING date night of his life… in hopes it will get him another shot with the woman he loves. Will it be worth the humiliation?  Part 2 We have NO IDEA who we’re dialing in today’s Second Date Update, we have a number, and a sneaking suspicion it might be a trap but only one way to find out! See omnystudio.com/listener for privacy information.

Kyle made ONE SLIGHT adjustment to his dating profile and he ended up matching with a woman he calls “The real deal.” So why does he need our help? We’ll figure it out in your Second Date Update! See omnystudio.com/listener for privacy information.

You may remember Brian and Olivia as a “Disney DO & Disney DON’T” couple where he was super into all things Disney and she was open to learning more…. But where are they now MONTHS after they first appeared on the show? Find out in your Second Date Update UPDATE! See omnystudio.com/listener for privacy information.

What’s the most embarrassing thing your date could catch you doing? David got caught at a bad time RIGHT as his date was meeting up with him and it happened AGAIN later on. We’ll help him try to recover in your Second Date Update podcast! See omnystudio.com/listener for privacy information.

Meeting your girlfriend’s parents can be stressful! It happened to Simon over a month ago, so why NOW does he need our help “fixing” what he says went wrong? Find out in a new Awkward Tuesday Phone Call! See omnystudio.com/listener for privacy information.

In today’s Second Date Update we found ourselves in the middle of a problem that is WAY out of our price range, even Brooke’s!  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: Thursday, October 8th, 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.

Part 1 5 minutes into his date with Delilah, Jack realized he forgot something MAJORLY important. Hear what slipped his mind and how we’re helping him gain back ground! Part 2 The listener in today’s Second Date Update says that if we can’t help him, it’ll be the first time EVER that he’s been rejected by a woman!  See omnystudio.com/listener for privacy information.

When we offered to send this couple on another date that WE PAY for, we never expected to get the answer back that we received. Hear one of the most bizarre endings to a Second Date Update ever! See omnystudio.com/listener for privacy information.

One woman has kept a secret from her bridal party for the last 6 years, and it probably explains why she cut contact with all of them the day after the wedding! See omnystudio.com/listener for privacy information.

Brian had so much fun on his date with Ariel, that at one point they were feeding each other food like animals! So, why isn’t she calling him back for more animal-style love? We’ll find out in your Second Date Update podcast! See omnystudio.com/listener for privacy information.

One of our listeners needs our help desperately before his apartment is completely EMPTY of all his belongings. He thinks his girlfriend has something to do with it, but he won’t know how to talk to her until we do an Awkward Tuesday Phone Call! See omnystudio.com/listener for privacy information.

Mike and Chrissy’s first date sounded like the start of a horror movie… Why was a mysterious stranger watching them silently the whole time?? We needed more details in the 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: Thursday, October 1st, 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.

Part 1 The woman in today’s Second Date Update agreed to meet up with a man before she even knew his name, and it’s all because of one grand romantic gesture. Part 2 For one of our listeners, the hottest thing that happened on her date was a game of CHARADES!  See omnystudio.com/listener for privacy information.

Hannah says that she and her date got into TWO arguments before they even got out of her driveway! Why would she even want to see him again? She’ll explain in your Second Date Update podcast! See omnystudio.com/listener for privacy information.

Out of all the Second Date Updates we’ve done in 2026, this one might have been the most viral! And we’ve got the couple back for a long awaited Second Date Update UPDATE! See omnystudio.com/listener for privacy information.

Vince is on the phone for a Second Date Update and he says the intimate parts of his relationship with Jamie are great but he want’s our help getting MORE SERIOUS than he’s ever been before! See omnystudio.com/listener for privacy information.

Last week we promised a guy that we’d help him come clean about losing his job and lying about it to his fiancé… but he snuck in another bombshell we didn’t see coming! Hear what it was during your Awkward Tuesday Phone Call podcast! See omnystudio.com/listener for privacy information.

The guy on the phone for today’s Second Date Update isn’t getting a call back, and it’s probably because the woman he’s interested in was on a DATE with ANOTHER MAN! He swears he can explain in the 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: Tuesday, September 22nd, 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.

Part 1 The guy on the phone today decided he would surprise his date with an unexpected guest during their dinner… Hear who it was in the podcast! Part 2 The guy in today’s Second Date clearly got his idea for a date from listening to our show, and we might owe him an apology, or at least some help trying to get another one!  See omnystudio.com/listener for privacy information.

Jack managed to secure a night over at Sarah’s place, but she CAUGHT HIM on the couch doing something he shouldn’t in the MIDDLE of the night! Find out what happened in your Second Date Update! See omnystudio.com/listener for privacy information.

One of our listeners thinks he has the chance to take the TRIP of a LIFETIME with one of his co-workers… if we can give him the right advice in your Awkward THURSDAY Phone Call! See omnystudio.com/listener for privacy information.

Cody admits “MISTAKES WERE MADE” on his date with Tiz. But, despite his failings he’s ready to reach out and try to make a better love connection in your Second Date Update podcast! See omnystudio.com/listener for privacy information.

How do you tell a close friend to get out of your house forever without ruining the friendship? We’ll try to figure it out the hard way during your Awkward Tuesday Phone Call podcast! See omnystudio.com/listener for privacy information.

Tracy gave Rob a VERY specific place he had to go in order to score a date with her. Was it worth his effort? Let’s find out 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: Thursday, September 17th, 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.

Part 1 One of our listeners did something THREE different times during their date… and while once might be strange, at the end it all made sense.  Part 2 One of our listeners admits SHE did something stupid, just to MEET a guy. Was it her idea? No. Was it effective? Let's find out! See omnystudio.com/listener for privacy information.

Beth is regretting rejecting Eddie, who happened to be wearing a certain “fashion accessory” and now she wants a do-over! We’ll see what magic we can work in your Second Date Update podcast! See omnystudio.com/listener for privacy information.

We've seen the texts and comments and we couldn't let Summer end without the "You Wouldn't Dare Summertime Challenge" happening! It's all going down at one time, in studio and there's some mystery meals ready for each and every host! See omnystudio.com/listener for privacy information.

The guy in today’s Second Date Update secretly planned a very informative and special date night for the woman he’s interested in. It’s one of the MOST ORIGINAL date ideas we’ve ever heard. See omnystudio.com/listener for privacy information.

One of our listeners is CERTAIN that the universe was talking to her when she met her DREAM MAN. The only problem? They kind met during a disaster and now she wants our help cleaning up after it! It's your Awkward Tuesday Phone Call! See omnystudio.com/listener for privacy information.

The woman in today’s Second Date Update knows she didn’t give strong signals to the guy she’s interested. In fact, she stayed FAR AWAY from him the whole night! We’ll dig into why 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: Thursday, September 10th, 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.

Part 1 One of our listeners came up with one of the CLEANEST & MOST FUN ice breaker questions we’ve ever heard… Part 2 The woman on the phone today described her date like a very famous film, but the comparison immediately had us all very concerned. See omnystudio.com/listener for privacy information.

SOMEONE drops the “L-word” on today’s upcoming Second Date Update and the only thing weirder than them saying it, is what happened the next day! See omnystudio.com/listener for privacy information.

SPEED was definitely a factor in Roman and Hailey’s blossoming relationship when they were first on our show months ago. But, today they’re back to fill us in and what’s happened since then in a Second Date Update UPDATE! See omnystudio.com/listener for privacy information.

One of our listeners tried a new way to meet single guys in real life, and she found herself in a dark room FULL of eligible bachelors! Hear about the surprising guy that she connected with in your Second Date Update! See omnystudio.com/listener for privacy information.

One overbearing mother got her son’s teacher to send an email to every parent in the class, and the drama its caused has shaken the school to its core and sucked us in for an Awkward Tuesday Phone Call! See omnystudio.com/listener for privacy information.

What one of our listeners did in a public park during her first date was definitely FREAKY. So much so, that it had us in studio wilding out! 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: Thursday, September 3rd, 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.

Part 1 Abbey had dates with TWO different guys, but could only pick one to pursue. Did she choose correctly?  Part 2 Miles’s closing move with Zoey was not only fun and flirtatious, it also comes with pizza. We guarantee guys are gonna try and steal this… See omnystudio.com/listener for privacy information.

One of our listeners felt INSTANT REGRET during his date and even tried to BAIL as soon as it started… But he stuck it out and now he wants our help with a Second Date Update! See omnystudio.com/listener for privacy information.

After 7 years apart we’re going to TRY to help one listener overcome the biggest romantic mistake he’s ever made, starting with getting his ex on the phone with us! See omnystudio.com/listener for privacy information.

Not all surprises are good surprises, and one of our listeners found that out the hard way! Hear what kind of trouble Ava and Dean found themselves in, in your Second Date Update podcast! See omnystudio.com/listener for privacy information.

One of our listeners was alone and had the urge to open his significant other’s computer, and what happened next lead to possible the most shocking Awkward Tuesday Phone Call of the year! See omnystudio.com/listener for privacy information.

Bobby didn’t come across in the best way the FIRST time he was on our show, but this time he SWEARS he’s changed and is now deserving of our help with a Second Date Update!  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: Tuesday, August 25th, 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.

Part 1 One of our listeners isn’t sure if his date meant to VANISH or if there was just miscommunication but you can tell us what you think after you hear it. Part 2 Today we’re shaking it up and doing an ALTERNATE version of our Second Date Update… Going to levels we’ve never gone to before! See omnystudio.com/listener for privacy information.

The guy in today’s Second Date was willing to do something that took A LOT of patience, selflessness, and understanding… hear if his sacrifice was worth it in the podcast! See omnystudio.com/listener for privacy information.

Two of our listeners will test the waters and see if they connect romantically when they speak to each other for the first time on our show! See omnystudio.com/listener for privacy information.

In today’s Second Date we learned about a dating app that NONE of us had even heard of before, and even though we were skeptical.. it helped one of our listener's secure his match! See omnystudio.com/listener for privacy information.

Imagine getting a text from your ex you haven’t seen in a year and she’s ECSTATIC about the WORST NEWS POSSIBLE… It happened to one of our listeners and he needs our advice in an Awkward Tuesday Phone Call! See omnystudio.com/listener for privacy information.

One of our listeners says he got a singular one-word text that let him know he BADLY screwed up his first date.  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: Tuesday, August 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.

Part 1 Cory took a PLANE FLIGHT to hang out with Alison… but their date left a lot to be desired… We’ll try to fix their future in your Second Date Update podcast! Part 2 One of our listeners took a BOLD step when she made a move on a guy while he was working… and seconds later they were inside her place getting familiar. See omnystudio.com/listener for privacy information.

Sasha is on the phone for today’s Second Date Update and she thinks the guy who left her his number is either her soulmate or a COMPLETE Scum Bag! Lucky for her, we've got a very special way to unveil the truth… See omnystudio.com/listener for privacy information.

Aria and Ryan managed to do the near impossible: start a romance thanks to our show! And now they’re BACK and you’ll find out what’s happened since they were last on thanks to a Second Date Update UPDATE! See omnystudio.com/listener for privacy information.

One of our listeners wanted to show his date he was a fun, outgoing guy, but what came out of his mouth is one of the CRINGIEST moments we’ve ever heard happen on a date!  See omnystudio.com/listener for privacy information.

One of our listeners says she’s dealing with a MONSTER problem with her mother-in law and her ridiculous demands are OUT OF CONTROL! We’ll try to help reel her in when we do an Awkward Tuesday Phone Call! See omnystudio.com/listener for privacy information.

One of our listeners says he has the PERFECT question that will tell him whether to STICK AROUND or RUN on a first date. Hear what it is 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: Tuesday, August 11th, 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.

Part 1 One of our listeners said he did EVERY FORM of communication he possibly could, leading up to his first date…. And something STILL went wrong….  Part 2 One of our listeners left his date with a GIFT that was ONLY supposed to be opened the next day… you’ll hear what it was, and how it backfired coming up! See omnystudio.com/listener for privacy information.

We’ve reached a pretty insane milestone with today’s Second Date and it happened with one of the nicest guys we’ve ever had on the show. See omnystudio.com/listener for privacy information.

One of our listeners met the PERFECT person at the wrong time. They went on a date nearly two decades ago that was INTERRUPTED halfway through… Now all these years later she wants to reconnect in a Closure Call! See omnystudio.com/listener for privacy information.

The “move” Sophia pulled at a restaurant on her date with Steve would either get you a second date OR get you kicked out of the building forever. Hear what it was in your Second Date Update podcast! See omnystudio.com/listener for privacy information.

One of our listeners is struggling with the news that his girlfriend wants to get plastic surgery… HOW does he respond and is it better to tell the truth or lie? We’ll help him out in an Awkward Tuesday Phone Call! See omnystudio.com/listener for privacy information.

One of our listeners got one of the BEST compliments a guy could get from a girl at the end of the night, but he’s PUZZLED why she’s not calling him back! We’re on the case 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: Wednesday, August 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.

Part 1 One of our listeners tried out the dating app PLENTY OF FISH… and you’re not gonna believe what happened on her very first meet up! Part 2 One of our listeners WISHES he did a better job cleaning up his car, because his entire night was ruined when his date found something between his seats. Find out what the incriminating item was in the Second Date Update podcast! See omnystudio.com/listener for privacy information.

One of our listeners went on a beach date and he gets huge props for one thing he DIDN’T DO… what was it? Find out in your Second Date podcast! See omnystudio.com/listener for privacy information.

One of our listeners has a delicate situation on her hands involving STOPPING her best friends proposal. She needs our help so she hit us up for some Textual Healing! See omnystudio.com/listener for privacy information.

A date at the movies went from your typical rom-com setting to an absolute HORROR scenario and now Sienna wants our help getting Evan to call her back!  See omnystudio.com/listener for privacy information.

Today we’re talking to a guy who has been nominated as the spokesperson for all the ticked off moms in his wife’s friend group, and his mission is to CONFRTON another mom about her kid’s birthday party. See omnystudio.com/listener for privacy information.

What’s the best way to get better at kissing? Is it just practice and experience? Or is there an expert out there that’s much closer than you might think? We’re answering that question 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 31st, 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.

Part 1 One of our listeners had a great first encounter with his date, but it was his FIRST TEXT after it ended that wrecked things…Part 2  A single phone call caused the guy in today’s Second Date Update to RUN OFF on his date with someone he called one of the most beautiful women he’s ever met! See omnystudio.com/listener for privacy information.

Chris and Teresa’s date STARTED with bubble tea, and ENDED with him TACKLING her in public. He says it’s a good thing, we’ll let you decide coming up in your Second Date Update! See omnystudio.com/listener for privacy information.

Denise and Caleb were on our show late last year and we got TONS of texts asking to follow up with them. We did and now they’re back to tell us all the romantic details that have happened since! It's a Second Date Update UPDATE! See omnystudio.com/listener for privacy information.

David brought Anne back to his place after their date, and when the front door randomly opened he was greeted by a grown man’s worst nightmare! Hear how it all went down in your Second Date Update! See omnystudio.com/listener for privacy information.

Would you ask your best friend to do something huge that goes against the unwritten rules of friendship? One of our listeners is doing just that and we have him on the line for an Awkward Tuesday Phone Call! See omnystudio.com/listener for privacy information.

Katrina spent the last 20 minutes of her date with Raymond LOCKED in her car by herself. Why would she do that? There’s a reason and you can hear it in the 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, July 24th, 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.

Part 1 One of our listeners discovered a little trick to exchange phone numbers with someone in public without uttering a SINGLE WORD… and the ladies seem to love it! Part 2 A request made at a dinner date might have crossed the line… but Kard says he was well within his rights on his date with Amy! Hear how it went down in your Second Date Update. See omnystudio.com/listener for privacy information.

Dating has become so complicated & expensive… where if you DON’T FEEL IT in the first 30 seconds… there’s NOW a sentence you can say…. that gives you an instant FREE PASS to get out of it… It happened to one of our listeners in today’s Second Date Update! See omnystudio.com/listener for privacy information.

For most people, high school drama ends when you graduate. But one of our listeners has a problem with his upcoming 20 year reunion and there’s only one person on this show who can save him! It's another edition of Brooke Breaks You Up! See omnystudio.com/listener for privacy information.

If your date ditches you in the middle of dinner is there ANY valid excuse that could earn forgiveness? It happened to Tara and now she wants our help figuring out why Norris ran out on her, in your Second Date Update! See omnystudio.com/listener for privacy information.

Normally, we help listeners with their romantic life, or crazy family drama, but today’s Awkward Tuesday Phone Call might be equal parts… BOTH?  See omnystudio.com/listener for privacy information.

A romance blossomed out of the ashes of a once-thought to be dead dating app… but then it all came crumbling down at a fancy Greek restaurant. We got the juicy details coming up in your Second Date Update podcast! See omnystudio.com/listener for privacy information.

Part 1 One of our listeners says a DEAFENING silence happened after an awkward question from their waiter on their date, and now she’s not getting a call back.  Part 2 The woman on the phone today claims that she discovered a place that is swarming with career driven, high-value men, and she even scored a date on her first visit. The problem? He's not calling her back! See omnystudio.com/listener for privacy information.

How far would you go to win over a beautiful woman who showed interest in you? One of our listeners went to the EXTREME and he might have gone too far because now he wants our help with an 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.com See 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.com See 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.com See 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.com See 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.com See 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.com See 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.com See 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.

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.

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.

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.

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.

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.

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.

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.

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.

One of our listeners says he DEFINITELY has someone to thank for his unforgettable date night. But the weird part is… that person isn’t exactly ALIVE…  See omnystudio.com/listener for privacy information.

We’re dealing with an INTERNATIONAL ROMANCE EMERGENCY in today’s Awkward Tuesday Phone Call! We’re putting all our efforts behind getting one woman to FINALLY pick up the phone for her boyfriend… See omnystudio.com/listener for privacy information.

Our listener on the phone today went out of his way to do the KIND, HONEST, and RESPECTFUL thing for his date… but it ended him up here with us and out of luck and love! Luckily, we can help him with 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: Wednesday, May 13th, 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.

Part 1 One of our listeners had the SHOCK OF A LIFETIME after being set up on a blind date by her friend. As soon as she showed up she knew something was very wrong… Part 2 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. See omnystudio.com/listener for privacy information.

The woman on the phone today shared a SHOCKING secret in today’s Second Date Update. We were cool with it at first but by the end of the call our jaws were on the floor!  See omnystudio.com/listener for privacy information.

Ashwin and Sierra came on our show a while back and we got SO many comments asking for more info, we HAD to bring them back for a Second Date Update UPDATE! Stay tuned to the end to hear from both of them and how their romance has gone since last time they spoke with us! See omnystudio.com/listener for privacy information.

One of our listeners refused to do things the easy way, and after he complicated drinks with his date, he thinks he knows the reason she’s not calling him back! We’ll see if he’s right in your Second Date Update podcast! See omnystudio.com/listener for privacy information.

One of our listeners found out what his girlfriend has been SECRETLY planning to give him for his birthday and he says he needs to STOP her IMMEDIATELY. Hear why in your Awkward Tuesday Phone Call! See omnystudio.com/listener for privacy information.

Our listener on the phone thinks that the reason he's not getting a call back is because of an argument he got into with a cashier during their date. He says it’s totally justified but he wants our assistance explaining! We'll do just that in the 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, May 8th, 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.

Part 1 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! Part 2 We promise you that you’ve never heard of anything like the move a guy pulled to ask out our listener outside a coffee shop. See omnystudio.com/listener for privacy information.

Dennis wrote a SONG for Taylor after their night out and he’s not getting a call back. In exchange for our help with a Second Date Update he’s gonna let us PLAY IT on air too! See omnystudio.com/listener for privacy information.

We’ve got two listeners who have never met but are open to love even if it comes out of one of the strangest segments we’ve ever tried! It's your "Blind Love Is?" podcast! See omnystudio.com/listener for privacy information.

Our listener invited herself along to run errands with her date and they actually had a pretty great time! But something about his dating profile is making her uneasy… Find out what that is in the Second Date Update podcast! See omnystudio.com/listener for privacy information.

The couple on the phone today had their FIRST ARGUMENT on Date #3 of their new relationship. She realizes she might have been in the wrong but before apologizing, she wants our help in an Awkward Tuesday Phone Call! See omnystudio.com/listener for privacy information.

The guy on the phone today pulled out the stops to take his date to a staged play, and even though the PLAY was magical, his evening must have been less than because he’s not getting a call back. See omnystudio.com/listener for privacy information.

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 feed, Brooke & Jeffrey! We'd love to hear your feedback...but please send all negative reviews to Jeffrey. FULL SHOW: Friday, May 1st, 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.

Part 1 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.  Part 2 Today’s Second Date Update is all about the 3 D’s – Dinosaurs, drinking and diamonds. Hear the call for yourself in the podcast! See omnystudio.com/listener for privacy information.

A weird little mix-up at the airport turned out to be a GOLDEN OPPORTUNITY FOR LOVE… You’ll hear about one of our listeners and his lucky accident in a Second Date Update! See omnystudio.com/listener for privacy information.

One of our listeners wants to take a HUGE LEAP with a very special person in his life… and if he doesn’t do it right, their 6-year friendship could be over. Get your Textual Healing podcast right here! See omnystudio.com/listener for privacy information.

The guy on the phone today says there’s ONE THING about his date that might give 99% of dudes “the ick” but it actually TURNS HIM ON. You’ll hear what it is in your Second Date Update! See omnystudio.com/listener for privacy information.

After a difficult situation ended up with Kash GHOSTING his ex Amber, he wants our help to navigate the murky waters of opening up contact again, in an Awkward Tuesday Phone Call! See omnystudio.com/listener for privacy information.

Our listener on the phone says his night ended with his date telling him “I’m glad you didn’t die.” It was a close call but he’s here with us for a Second Date Update! See omnystudio.com/listener for privacy information.

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 feed, Brooke & Jeffrey! We'd love to hear your feedback...but please send all negative reviews to Jeffrey. FULL SHOW: Friday, April 24th, 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.

Part 1 Today’s Second Date Update includes probably the MOST AWKWARD 20 minutes of a first date we’ve ever had on this show. And it’s all because of an embarrassing run-in that happened at a bar! Part 2 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.

Mike only had one shot to plan a night that Elise would never forget and what happened was definitely memorable… but was it a good memory? Find out in your Second Date Update podcast! See omnystudio.com/listener for privacy information.

We always talk about “the one who got away” but what about “The one who won’t go away?” We’re diving into it when Joe and Sabrina return to our show for a new Second Date Update UPDATE! See omnystudio.com/listener for privacy information.

There’s a NEW dating term we heard today and whether it’s good or bad, we think it’s gonna catch on SOON to describe a certain type of person… Hear it in your Second Date Update podcast! See omnystudio.com/listener for privacy information.

One of our listeners couldn’t believe his LUCK and WHO he ended up across from during a speed dating event. It led him all the way to us and your Awkward Tuesday Phone Call! See omnystudio.com/listener for privacy information.

For a minute during her date, our listener on the phone today thought she was out with the most POPULAR guy in town. But is that everything it’s cracked up to be? Find out in your Second Date Update podcast! See omnystudio.com/listener for privacy information.

Part 1 A mysterious handwritten note was dropped onto the table during our listener's date and it altered both of their lives forever! Part 2 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.

The guy on the phone today got an EMERGENCY call on the way to his date, and it put him in a definite lose-lose situation. Tell us what you would have done, once you hear the Second Date Update! See omnystudio.com/listener for privacy information.

In a new relationship there’s tons of little things that could give you the “ick.” We’re gonna help one of our listeners navigate AWAY from those icebergs with some Textual Healing! See omnystudio.com/listener for privacy information.

What started as a romantic one on one date ended with one of our listeners sandwiched between three gorgeous women all night. He’ll explain how he did it coming up in your Second Date Update! See omnystudio.com/listener for privacy information.

One of our listeners needs our advice on how to turn someone down. But it’s not just anyone… it’s someone in their own family! We’ll explain more in an Awkward Tuesday Phone Call! See omnystudio.com/listener for privacy information.

What do you do if you’re the ONE PERSON who didn’t get the memo that you’re supposed to bring a gift to the party? One of our listeners had a GENIUS save when that happened to him and it even got him a DATE at the same time! See omnystudio.com/listener for privacy information.

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 feed, Brooke & Jeffrey! We'd love to hear your feedback...but please send all negative reviews to Jeffrey. FULL SHOW: Wednesday, April 8th, 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.

Part 1 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... Part 2 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 Second Date Update! See omnystudio.com/listener for privacy information.

One of our listeners says it's hard to meet genuine guys who are sensitive to her unique situation, she’ll share what that is in a Second Date podcast! See omnystudio.com/listener for privacy information.

For the first time in the history of our show, the person who asked us for help almost REFUSED to hear the truth once we got in touch with their long lost friend…  See omnystudio.com/listener for privacy information.

The woman on the phone today saw something very personal on a guy's book shelf during their first date, and she was so bewildered, she reached out to us as soon as she could!  See omnystudio.com/listener for privacy information.

The woman on the phone today is upset that her childhood best friend NO-SHOWED her wedding a few weeks ago… And we're going to find out the reason why in an Awkward Tuesday Phone Call! See omnystudio.com/listener for privacy information.

The woman on the phone today tried to take the lead on her date, and her surprise was her own MOTHER. We're not joking, it really happened and you can hear how it went down in your Second Date Update Podcast! See omnystudio.com/listener for privacy information.

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 feed, Brooke & Jeffrey! We'd love to hear your feedback...but please send all negative reviews to Jeffrey. FULL SHOW: Friday, April 3rd, 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.

Part 1 One of our listeners was DITCHED on a date in a brazen way, so today we’re on the hunt for ANSWERS. Part 2 One of our listeners is confused after his date ended in the WEIRDEST way ever… but he still has some interest... See omnystudio.com/listener for privacy information.