Brooke and Jeffrey: Second Date Update

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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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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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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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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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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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

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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

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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

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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.

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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!

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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!

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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!

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Normally, we help listeners with their romantic life, or crazy family drama, but today’s Awkward Tuesday Phone Call might be equal parts… BOTH? 

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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!

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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!

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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! 

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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!

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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!

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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!

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One of our listeners says she found an UNDERRATED place for ladies to meet QUALITY guys… and it might shock you where. 

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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, July 8th, 2026

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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!

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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!

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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!

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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. 

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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!

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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!

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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 3rd, 2026

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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!

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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!

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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!"

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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.

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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.

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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!

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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, June 24th, 2026

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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!

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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!

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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?

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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. 

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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!

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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! 

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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: Thursday, June 18th, 2026

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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.

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One of our listeners got maybe the worst possible response to an unsolicited text message… EVER!

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It’s a favorite of the listeners and the bane of Brooke’s existence… We’re doing another edition of “BROOKE BREAKS YOU UP!”

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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!

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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!

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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!

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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, June 12th, 2026

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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.

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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! 

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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!

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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? 

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