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Brooke and Jeffrey: Second Date Update

Brooke and Jeffrey: Second Date Update

2,129 episodes — Page 2 of 43

Second Date Update: Sunset Scribbles

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.

Mar 23, 202619 min

FULL SHOW: Disney Adult Date, José’s Meet n Greet Fail + Brooke’s Snack Wars (3/18/26)

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: Youtube Instagram TikTok BrookeandJeffrey.comSee omnystudio.com/listener for privacy information.

Mar 22, 20261h 5m

Second Date Update Classics: Ride of Shame + Incriminating News at 11

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…See omnystudio.com/listener for privacy information.

Mar 21, 202636 min

Second Date Update: The Best Listener Ever

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!See omnystudio.com/listener for privacy information.

Mar 20, 202618 min

Alexis Asks You Out: Make Out Mess Up

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

Mar 19, 202618 min

Second Date Update: A Whole New Girlfriend

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!See omnystudio.com/listener for privacy information.

Mar 18, 202617 min

Awkward Tuesday: Fantasy Fail

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!See omnystudio.com/listener for privacy information.

Mar 17, 202619 min

Second Date Update: Ghost Date Hijack

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! See omnystudio.com/listener for privacy information.

Mar 16, 202619 min

Second Date Update Classics: A Picture Says A Thousand Icks + Appetizer Energy, Entrée Problems

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. See omnystudio.com/listener for privacy information.

Mar 14, 202636 min

Second Date Update: Champagne and Shackles

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!See omnystudio.com/listener for privacy information.

Mar 13, 202617 min

Textual Healing: License To Bill

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!See omnystudio.com/listener for privacy information.

Mar 12, 202619 min

Second Date Update: High Steaks Heartbreak

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!See omnystudio.com/listener for privacy information.

Mar 11, 202618 min

Awkward Tuesday: Private Jet For My Nervous Pet

Today’s Awkward Tuesday Phone Call involves a private plane, a nervous pet, and one BIG question that our listener needs help asking.See omnystudio.com/listener for privacy information.

Mar 10, 202618 min

Second Date Update: Sweet Benjamin and His Big Sis

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!See omnystudio.com/listener for privacy information.

Mar 9, 202618 min

FULL SHOW: Jeff’s Pizza Parody, Riffin’ Around Marching Bands + Reverse Catfish Date (3/6/26)

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: Youtube Instagram TikTok BrookeandJeffrey.comSee omnystudio.com/listener for privacy information.

Mar 8, 20261h 5m

Second Date Update Classics: The Rudy of Dating + Date Night Veto

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!See omnystudio.com/listener for privacy information.

Mar 7, 202636 min

Second Date Update: Taking The Plunge

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! See omnystudio.com/listener for privacy information.

Mar 6, 202618 min

Second Date Update UPDATE: Gucci First Questions Later

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!See omnystudio.com/listener for privacy information.

Mar 5, 202617 min

Second Date Update: Late Night Lab Experiment

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!See omnystudio.com/listener for privacy information.

Mar 4, 202618 min

Awkward Tuesday: CTRL ALT EX

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!See omnystudio.com/listener for privacy information.

Mar 3, 202618 min

Second Date Update: Pawn Shop Shopping Trip

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!See omnystudio.com/listener for privacy information.

Mar 2, 202618 min

FULL SHOW: Chicken Tender Lovin Date, José's a Dad? + Alexis’ Gross Plane Emergency (2/25/26)

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: Youtube Instagram TikTok BrookeandJeffrey.comSee omnystudio.com/listener for privacy information.

Mar 1, 20261h 7m

Second Date Update Classics: Right To Remain Sexy + Scooter Safety Patrol

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!See omnystudio.com/listener for privacy information.

Feb 28, 202638 min

Second Date Update: Two Year Ghost Job

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!See omnystudio.com/listener for privacy information.

Feb 27, 202618 min

Awkward Thursday: The Name Game

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!See omnystudio.com/listener for privacy information.

Feb 26, 202618 min

Second Date Update: So Turned On

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!See omnystudio.com/listener for privacy information.

Feb 25, 202618 min

Awkward Tuesday: Met At My Wedding

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!See omnystudio.com/listener for privacy information.

Feb 24, 202618 min

Second Date Update: Bros Before Kim

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.

Feb 23, 202618 min

FULL SHOW: Double Kiss Surprise Date, Dumbest Lies Ever + Battle of the Tinder Dates (2/18/26)

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: Youtube Instagram TikTok BrookeandJeffrey.comSee omnystudio.com/listener for privacy information.

Feb 22, 20261h 3m

Second Date Update Classics: Ex Marks The Shot + Better Late Than Never

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! See omnystudio.com/listener for privacy information.

Feb 21, 202637 min

Second Date Update Classic: Saved By The Shrimp

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!See omnystudio.com/listener for privacy information.

Feb 20, 202618 min

Textual Healing: Take A Dip In Rent

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!See omnystudio.com/listener for privacy information.

Feb 19, 202618 min

Second Date Update Classic: Double Kiss Surprise

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… See omnystudio.com/listener for privacy information.

Feb 18, 202617 min

Awkward Tuesday: What If?

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!See omnystudio.com/listener for privacy information.

Feb 17, 202619 min

Second Date Update Classic: Motel 7

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.See omnystudio.com/listener for privacy information.

Feb 16, 202618 min

FULL SHOW: Jeff’s Love Song for Three, V-Day 2nd Date Edition + Riffin Around Romance (2/13/26)

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: Youtube Instagram TikTok BrookeandJeffrey.comSee omnystudio.com/listener for privacy information.

Feb 15, 20261h 11m

Second Date Update Classics: Scam the Scammer + V-Day Pass Out

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!See omnystudio.com/listener for privacy information.

Feb 14, 202635 min

Second Date Update Classic: Valentine's Day Fork

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.See omnystudio.com/listener for privacy information.

Feb 13, 202618 min

Second Date Update UPDATE: Family Dinner Drama

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!See omnystudio.com/listener for privacy information.

Feb 12, 202618 min

Second Date Update: Universe Is Busy

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!See omnystudio.com/listener for privacy information.

Feb 11, 202619 min

Awkward Tuesday: Theories We Don't Like

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!See omnystudio.com/listener for privacy information.

Feb 10, 202618 min

Second Date Update: Hired A Hinge Coach

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!See omnystudio.com/listener for privacy information.

Feb 9, 202618 min

FULL SHOW: Errand of Love Date, AI Sabotaging Our Show + Brooke’s Ruining Our YouTube (2/4/26)

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: Youtube Instagram TikTok BrookeandJeffrey.comSee omnystudio.com/listener for privacy information.

Feb 8, 20261h 8m

Second Date Update Classics: Car Talk + I Woke Up Where?

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! See omnystudio.com/listener for privacy information.

Feb 7, 202636 min

Second Date Update: Unattractive Trey Is Back

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!See omnystudio.com/listener for privacy information.

Feb 6, 202618 min

Closure Call: The One Who Got Away

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!See omnystudio.com/listener for privacy information.

Feb 5, 202619 min

Second Date Update: My Ears Are Clogged With Love

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!See omnystudio.com/listener for privacy information.

Feb 4, 202618 min

Awkward Tuesday: Consent For Content

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!See omnystudio.com/listener for privacy information.

Feb 3, 202618 min

Second Date Update: No Snow Show

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! See omnystudio.com/listener for privacy information.

Feb 2, 202619 min

FULL SHOW: Romantic Corndog Date, Brooke’s Theater Debut & José’s Bathroom Encounter (1/28/26)

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, January 28th, 2026 Curious if we look as bad as we sound? Follow us @BrookeandJeffrey: Youtube Instagram TikTok BrookeandJeffrey.comSee omnystudio.com/listener for privacy information.

Feb 1, 20261h 7m