Brooke and Jeffrey: Second Date Update

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

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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

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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

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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

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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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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:

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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

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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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Our listener, Jason, has NO IDEA what went wrong on his date with Riley, but SOMETHING must have happened based on how things ended. He asked for our help and we’re ready to dive in, in your Second Date Update podcast!

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Humiliation happened not once but THREE SEPARATE TIMES to one of our listeners, but he’s not ready to give up. In fact, he wants our help with an Awkward Thursday Phone Call and we’re gonna give it to him in the podcast!

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One of our listeners purposely arrived OVER AND HOUR AHEAD of their date, and you’ll never believe what they used that time to prepare for. Find out if it backfired or helped in your Second Date Update!

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The woman on the phone today DEEPLY regrets the compliment she paid to a guy, he took it the WRONG WAY and now Jose and Brooke are gonna have to dig deep for some advice in your Awkward Tuesday Phone Call podcast!

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What’s the boldest move a woman can make on the first date? Our listener on the phone today fears she might have pushed it in her interaction but we’re ready to help her get 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, March 27th, 2026

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

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Part 1

One of our listeners had women FLOCKING to him thanks to one subtle change to his wardrobe. Hear what it was in your Second Date Update.

Part 2

When a listener describes his date as an "unconventional beauty", we're going to try to uncover if that's the reason she isn't calling him back!

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You’re gonna be shocked when you hear how BRIEF the conversation was that brought our listeners date to a COMPLETE and INSTANT STOP. Avoid this sentence if you can, once you hear it, in your Second Date Update podcast!

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One of our listeners ended up on a 10-hour long marathon first date and the only thing more shocking than that... is what happened after we hung up the phone! It’s a Second Date Update UPDATE!

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Our listener wasn’t TRYING to find a romantic connection, it was her 7 year old DAUGHTER who wanted to do it for her. Hear how a sneaky 2nd grader introduced MOMMY to an eligible bachelor in your Second Date Update podcast! 

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Lyndsey heard what romantic gesture her boyfriend of 4 months was trying to pull off for her and she is ADAMANT that we help her STOP HIM at ALL COSTS! 

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The woman on the phone today says not only was her date a “solid 9” but the date he planned for them put him head and shoulders above the rest! So why isn’t he calling her back? Find out in the 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: Wednesday, March 18th, 2026

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

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Part 1

How can you parlay one night of fun with a person you met at the club into something more meaningful? We're going to help one of our listeners try to do exactly that.

Part 2

One of our listeners got their 15 seconds of fame DURING A DATE and it included tv cameras recording EVERYTHING he said…

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James came on our show a few months ago and actually USED his previous experience to change for the better?? Hear how he’s worked to become a better DATER in your Second Date Update podcast!

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After “Brooke Breaks You Up” was such a controversial, but rousing success, we’re trying a NEW segment for the first time ever today...

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One of our listeners REGRETS being honest about his favorite hobby… he knows it can be a red flag for some women and he’s hoping we can help smooth it over in your Second Date Update podcast!

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One of our listeners managed to ruin a LONG TIME friendship with ONE single sentence… He’s ready to risk anything to take it back so we’re setting him up with an Awkward Tuesday Phone Call!

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Our listener says his date got totally derailed by an anonymous stranger and if he doesn’t find out WHO the veiled figure is, he may never get another shot to take Mysty to dinner! 

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Part 1

The guy on the phone today claims his date said one specific thing to their waiter that wasn't just a green flag...but made him instantly realize she was relationship material!

Part 2

One of our listeners THOUGHT he had a second chance all lined up with his date, but a single one-word text message brought that reality crashing down. 

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One of our listeners ended up in the bathroom alongside her date and NOT in a good way… You’ll hear why she had no choice but to bring him with her in a Second Date Update!

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One of our listeners wants to make a BIG MOVE with a woman he’s known for 6 DAYS. You’ll hear it, and why he needs our help pulling it off with some Textual Healing!

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One of our listeners found the ULTIMATE HACK to take a woman out, without breaking the bank. It requires a tad bit of deception though… find out more in your Second Date Update podcast!

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Today’s Awkward Tuesday Phone Call involves a private plane, a nervous pet, and one BIG question that our listener needs help asking.

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The guy looking to score another hangout with date isn’t even on the phone with us! Someone else is doing the call IN HIS PLACE! Find out who it is in your 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, March 6th, 2026

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

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Part 1

The guy on the phone for today’s Second Date Update says we need to get him ANSWERS, not just for his sanity, but for his FRIEND GROUP who played a strange role in his date.

Part 2

One of our female listeners used an innocent little excuse…. To go from awkward end of the night hug… to Instant sleepover at his place… Your gonna hear how she did it!

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One of our listeners was MORTIFIED when her date accidentally saw something that was NEVER intended for his eyes… She needs our help with a Second Date Update! 

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Is it better to find true love or a rich guy with a big boat? Today we’ll finally learn the answer in a special Second Date Update UPDATE!

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One of our listeners says she found the EXACT right time to strike up a conversation with the cutest guy in the room… Find out how the shy science girl got the courage to do it, in your Second Date Update podcast!

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The guy on the phone today had not one, but TWO women asking to be his Valentine, and rather than figure it out himself, he’s tasking us with sorting through the chaos in an all new Awkward Tuesday Phone Call!

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