Brooke and Jeffrey: Second Date Update

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

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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

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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

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

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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!

See omnystudio.com/listener for privacy information.

We're trying out a new idea for our fans of the 2nd Date Update! Every Sunday, we will be hosting one of our FULL HOUR episodes from our main show feed, Brooke & Jeffrey! We'd love to hear your feedback...but please send all negative reviews to Jeffrey.

FULL SHOW: Wednesday, 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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The listener on the phone today TRIED to buy a woman a gift in the middle of their date, but he never actually GOT it and the reason WHY is actually pretty hilarious. It's 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: Wednesday, February 25th, 2026

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

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Part 1 

One of our listeners says HIS DATE asked him to do something UNUSUAL shortly after they sat down, and he thinks it's part of why he’s not getting a call back.

Part 2

The guy on the phone today had a run-in with a woman who wouldn’t stop SCREAMING at him during his first date. You’re not gonna believe the topic that set her off!

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The woman on the phone admits what she did to her date was LOWER than LOW. Now, two years later, she’s finally ready to make it right, in a Second Date Update!

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One of our listeners was taken by surprise by her boyfriend and now she wants our help to try and get him to TAKE IT BACK… without hurting his feelings! It’s an Awkward THURSDAY Phone Call!

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One of our listeners thinks that playing with his FOOD is part of the reason why he isn’t getting a call back… Only way to know for sure is to have him on for a Second Date Update!

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The woman on the phone today is INCREDIBLY nervous and flustered all over a guy she hasn’t SEEN or SPOKEN TO for 3 years! It’s one of our most entertaining Awkward Tuesday Phone Calls we’ve ever had!

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One of our listeners says he was given no choice but to LIE right to his date’s face… Cuz if he was Truthful about why he REALLY had to suddenly leave... she’d probably never talk to him again.

See omnystudio.com/listener for privacy information.

We're trying out a new idea for our fans of the 2nd Date Update! Every Sunday, we will be hosting one of our FULL HOUR episodes from our main show feed, Brooke & Jeffrey! We'd love to hear your feedback...but please send all negative reviews to Jeffrey.

FULL SHOW: Wednesday, February 18th, 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

We were shocked when we heard about our listeners tense situation that went down on a first date with an UNEXPECTED VISITOR…

Part 2

Something happened to our listener on his way to the first meetup with his date, and it changed the trajectory of their entire night! 

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The guy in today’s Second Date had to do something DRASTIC in order to save his date from going off the rails. Find out what it was in the podcast!

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One of our listeners caught her landlord in a very compromising position and what she does next could either be the SMARTEST or DUMBEST move of her entire life. We’re gonna help her with some Textual Healing!

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One of our listeners was trying to walk a thin line in trying to get a man to notice her, and pulled a move that maybe went a little too far… 

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One of our listeners wants closure or else she’s always going to regret a moment from her past. We’re gonna try to help her in an Awkward Tuesday Phone Call!

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The guy in today’s Second Date had ONE SHOT and ONE NIGHT with a woman while she was in town… and he admits… some weird stuff happened.

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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, February 13th, 2026

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

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Part 1

One of our listeners is FURIOUS after her date left her in the most embarrassing situation of her life… and now she wants not just answers, but REVENGE.

Part 2

One of our listeners ended up in the HOSPITAL right in the middle of his first date… and he can’t believe he was naïve enough to make this dumb, avoidable choice… You’ll hear it in a special Valentine’s Day Second Date Update!

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Cupid needs our help with a Valentine’s Day emergency! The woman on the phone says they were KICKED OUT of a restaurant on their date but she insists it was one of the best meetups she’s ever had.

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Gillian and Thomas were on our show a few months ago after some drama happened on their date over a family recipe. Now, they’re BACK for a special Second Date Update UPDATE!

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One of our listeners SWEARS she found the fool-proof method to turn your dream guy into a reality! She’ll explain how she manifested him in your Second Date Update podcast!

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In today’s Awkward Tuesday Phone Call, a MASSIVE SECRET gets revealed that shocked not only our listener but EVERY SINGLE PERSON in the room!

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The guy on the phone today hired a PRO dating coach, and says he learned one line that worked INSTANTLY to attract a quality woman. You can STEAL it once you find out what 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: Wednesday, February 4th, 2026

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

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BrookeandJeffrey.com

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Part 1

The woman on the phone today got an INTERESTING surprise when she got into her date's car, and that kind of weirdness is something we can all get behind on this show!

Part 2

One of our listeners needs our help piecing together his night because he woke up not in his bed, not in her bed, and not even in a bed at all! 

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One of our listeners did something HEROIC for a stranger, and it got him a date! Meet our hero in today's Second Date Update!

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12 years ago, things ended between one of our listeners and the man of her dreams. She’s always wondered what happened with him, and in a brand-new Closure Call we’re about to find out!

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The woman on the phone today was taken on one of the LEAST romantic dates we’ve ever heard of, and she says she CAN’T STOP thinking about the guy! We’ll try to track him down in a Second Date Update!

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One of our listeners found some unexpected fame, and now THOUSANDS of people know his name. And it created a weird issue that only an Awkward Tuesday Phone Call can fix!

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The woman on the phone today learned the HARD WAY after her date promised to give her a luxurious “experience of a lifetime” that she shouldn’t be so quick to trust. She’s ready to call him out in a Second Date Update! 

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