Brooke and Jeffrey: Second Date Update

Every Sunday, we host one of our FULL HOUR episodes from our main show feed Brooke & Jeffrey, and incase you missed it, here's our extra spooky Halloween show!

FULL SHOW: Friday, October 30th, 2026

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Part 1

The couple in today’s Second Date Update went to a haunted house for their first date, but only one of them came out, and now HE wants our help getting ahold of the woman!

Part 2

No party is better for random makeouts than a Halloween Party! One of our listeners was close to getting lucky but fate (or something else) intervened and now she needs a Second Date Update!

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Everyone in the room might have been shrieking at the time but that’s the moment Shawn knew he was in love! Can he regather the girl that’s been ghosting him? Find out in your Second Date Update!

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It has a 0% success rate but that’s not gonna stop us! We sent Ashton out for REVERSE TRICK OR TREATING to see if someone will let him into their home!

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One of our listeners was SO RELAXED on her night out with Vince, that she did something unintentional and kind of embarrassing. She thinks it’s probably why she needs our help with a Second Date Update!

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Today’s Halloween Edition of the Awkward Tuesday Phone Call is a mortifying conversation between two people who REALLY don’t like each other anymore!

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One of our listeners said he met a woman during the spookiest time of the year but he never expected to be GHOSTED! We’re investigating and digging in for him in your Halloween Second Date Update!

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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: Wednesday, October 21st, 2026

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Part 1

Jake and Kim bonded on their date over their shared HATE for one specific thing… But now she’s not calling back? Maybe we can get her to explain coming up in your Second Date Update!

Part 2

All Anthony had to do to make himself PERFECT for his date is change TWO PHYSICAL things about himself…and of course it completely backfired.

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Daniel was DESPERATELY trying to avoid answering one specific question on his date with Lilly. It got asked, it DIDN’T go well, and now he wants our help figuring out how to put the pieces back together in your Second Date Update!

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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!

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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… 

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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!

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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!

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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

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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!

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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!

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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!

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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!

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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!

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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! 

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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

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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! 

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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!

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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!

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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!

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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!

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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!

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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

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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! 

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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!

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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!

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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!

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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!

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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!

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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

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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! 

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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!

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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!

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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!

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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!

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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!

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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

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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!

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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!

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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!

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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.

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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!

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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!

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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

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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.

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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!

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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!

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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!

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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!

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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!

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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

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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…

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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!

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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!

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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!

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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!

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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! 

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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

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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!

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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!

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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!

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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!

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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!

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

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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

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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.

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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…

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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!

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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! 

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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!

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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! 

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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

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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!

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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.

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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!

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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!

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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!

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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!

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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:

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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!

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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!

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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!

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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! 

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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.

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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!

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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:

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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!

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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!

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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!

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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!

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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!

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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!

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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:

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