Brooke and Jeffrey: Second 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, 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

Curious if we look as bad as we sound? Follow us @BrookeandJeffrey:

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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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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!

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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!

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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, June 5th, 2026

Curious if we look as bad as we sound? Follow us @BrookeandJeffrey:

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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.

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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!

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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!

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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!

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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!

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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!

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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, May 29th, 2026

Curious if we look as bad as we sound? Follow us @BrookeandJeffrey:

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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!

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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!

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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!

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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!

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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!

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One of our listeners admits she broke more than FIVE unwritten rules of dating, but she says she had a good reason too! 

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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: Monday, May 18th, 2026

Curious if we look as bad as we sound? Follow us @BrookeandJeffrey:

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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…

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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!

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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!

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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… 

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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…

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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!

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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, May 13th, 2026

Curious if we look as bad as we sound? Follow us @BrookeandJeffrey:

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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.

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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! 

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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!

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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!

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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!

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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!

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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, May 8th, 2026

Curious if we look as bad as we sound? Follow us @BrookeandJeffrey:

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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.

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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!

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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!

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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!

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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!

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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.

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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:

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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!

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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!

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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!

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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!

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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!

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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!

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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:

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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).

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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!

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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!

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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!

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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!

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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!

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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!

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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!

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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!

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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!

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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!

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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!

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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

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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!

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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!

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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… 

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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! 

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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!

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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!

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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:

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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...

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