Brooke and Jeffrey: Second Date Update

Second Date Update: Lonely Cannoli

09 Jun 2025

Contributed by Lukas

A quick trip to move his car ended up being a HUGE mistake for our listener, and it sent his date WILDLY OFF TRACK. Hear how it went down in a brand n...

Textual Healing: Ex-pectations

08 Jun 2025

Contributed by Lukas

We've got a special new episode you this weekend! Normally on this show we try to HELP make a romantic connection but coming in today’s Textual ...

Second Date Update Classics: 2nd Chance Scott + Mysterious Wallet Situation

07 Jun 2025

Contributed by Lukas

Part 1 One of our listeners took a woman on a BEACH DATE and he gets huge props for one thing he DIDN’T DO… what was it? We're going to f...

Second Date Update: 1st Impressions Are Everything

06 Jun 2025

Contributed by Lukas

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 p...

Second Date Update: Meal Me Once

04 Jun 2025

Contributed by Lukas

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 swea...

Awkward Tuesday: False Setto Freakout

03 Jun 2025

Contributed by Lukas

One of our listeners is dealing with a difficult type of neighbor drama. You’re gonna want to hear our advice coming up in a brand new Awkward T...

Second Date Update: One Year Later To Rejection King

02 Jun 2025

Contributed by Lukas

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...

Say Yes to the Ex: Unlucky Number 13

01 Jun 2025

Contributed by Lukas

We've got a special new episode you this weekend! It’s easy to say yes to some things, but saying YES to your EX is another story… After ...

Second Date Update Classics: Picture Says It All + Promotion Commotion

31 May 2025

Contributed by Lukas

Part 1: One of our listeners figured out a way to get his entire evening PAID FOR, and it involved no lying, not scheming and not cheating. How did it...

Second Date Update: Yup Date for Jessica

30 May 2025

Contributed by Lukas

A mysterious handwritten note was dropped onto the table during our listener's date and it altered both of their lives forever! Hear what it said comi...

Second Date Update: Three Wheelin' It

28 May 2025

Contributed by Lukas

One of our listeners is confused after his date ended in the WEIRDEST way ever… but he still has SOME interest, so it couldn’t be that ba...

Awkward Tuesday: Birthday Scamazon

27 May 2025

Contributed by Lukas

One of our listeners was SHOCKED by the children’s birthday invite her son received… in fact, all the parents were so bothered by the str...

Second Date Update Classic: The Blame Game

26 May 2025

Contributed by Lukas

In the podcast you can hear the SHOCKING and UNFORTUNATE events that happened during our Second Date Update – and they were all totally Brooke&r...

True Confessions: School Edition

25 May 2025

Contributed by Lukas

We've got a special new episode you this weekend! Can you figure out which of these embarrassing stories from our high school days are true and which ...

Second Date Update Classic: Scam the Scammer

24 May 2025

Contributed by Lukas

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...

Second Date Update: First Date Demise

23 May 2025

Contributed by Lukas

We guarantee once you hear today’s Second Date Update that you’ll be cheering for single school teacher Marianne to find her true love!&nb...

Second Date Update: Hang Up On Him

21 May 2025

Contributed by Lukas

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...

Awkward Tuesday: Sharing Aaron

20 May 2025

Contributed by Lukas

One of our listeners came across an overbearing mother and what went down between them is either gonna be the biggest misunderstanding ever, or the mo...

Second Date Update: Unconventional Beauty and the Feast

19 May 2025

Contributed by Lukas

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!See om...

Textual Healing: Peek A Boo Your Neighbor Can See You

18 May 2025

Contributed by Lukas

We've got a special new episode you this weekend! One of our listeners caught his neighbor doing something that's making him very uncomfortable... it'...

Second Date Update Classic: The Birthday Trick

17 May 2025

Contributed by Lukas

One of our listeners managed to make a genuine connection with a woman, all because of one trick he’s been using for YEARS! Hear what it is in y...

Second Date Update: The Ride Of Shame

16 May 2025

Contributed by Lukas

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 ...

Second Date Update UPDATE: Bumpin' Carts

15 May 2025

Contributed by Lukas

Today is proof that just because we think a relationship is doomed doesn't mean anything... because one of the most unexpected couples we've had on ou...

Second Date Update: The First Five Seconds

14 May 2025

Contributed by Lukas

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 c...

Awkward Tuesday: Guy In A Tree

13 May 2025

Contributed by Lukas

One of our listeners met a guy at a house party and says he literally RISKED HIS LIFE to not get caught with her! Now she wants answers! We're going t...

Second Date Update: Flirt and Observe

12 May 2025

Contributed by Lukas

One of our listeners says she experienced an intimate moment with a guy she’d never met, when they were in a crowded coffee shop at the same tim...

Say Yes To The Ex: Podcast Problems

11 May 2025

Contributed by Lukas

We've got a special new episode you this weekend! One of our listeners got dumped a few months ago during an argument about TOENAILS... But now, he sw...

Second Date Update Classic: Red Envelope Regret

10 May 2025

Contributed by Lukas

If only finding a date was as easy as ordering your favorite drink. One of our listeners had the perfect girl right in front of him all thanks to a ne...

Second Date Update: A Picture Says A Thousand Icks

09 May 2025

Contributed by Lukas

Our listener 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...

Second Date Update: Date Night Veto

07 May 2025

Contributed by Lukas

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&...

Awkward Tuesday: Cheating Across Continents

06 May 2025

Contributed by Lukas

One of our listeners is facing a huge moral dilemma, does she mind her own business, or possibly ruin her friends relationship?See omnystudio.com/list...

Second Date Update: Street Walker Love Story

05 May 2025

Contributed by Lukas

One of our listeners turned a super awkward moment into an actual MEET CUTE that almost seemed TOO perfect. You’ll hear it in a brand new Second...

Blind Love Is? Automatic Yes & 20 Seconds of Silence

04 May 2025

Contributed by Lukas

We've got a special new episode you this weekend! Two single listeners will meet for the very first time on our show SIGHT UNSEEN… to see if ch...

Second Date Update Classic: Five Finger Hangout

03 May 2025

Contributed by Lukas

Someone’s phone alarm going off in the middle of the date set off the WILDEST part of their entire evening. Hear what it was for in your Second ...

Second Date Update: Right To Remain Sexy

02 May 2025

Contributed by Lukas

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

Second Date Update: Better Late Than Never

30 Apr 2025

Contributed by Lukas

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

Awkward Tuesday: Bridesmaid Contract

29 Apr 2025

Contributed by Lukas

Our listeners love dysfunctional relationships so much, we didn't wanna deprive you. Here's a segment from our Full Show feed, 'Brooke and Jeffrey', &...

Second Date Update: Ex Marks The Shot

28 Apr 2025

Contributed by Lukas

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

Say Yes To The Ex: Sims City Blues

27 Apr 2025

Contributed by Lukas

We've got a special new episode you this weekend! One of our listeners is having communication issues with her relationship, but it’s not as sim...

Second Date Update Classic: Ross Mess For Less

26 Apr 2025

Contributed by Lukas

We had to try our best to get the woman on the phone to tell us the TRUTH about what happened on her date… and it might be the most embarrassin...

Second Date Update: Appetizer Energy, Entrée Problems

25 Apr 2025

Contributed by Lukas

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....

Second Date Update UPDATE: A Quiet Place

24 Apr 2025

Contributed by Lukas

The couple on the phone today were so sweet and cute the last time they appeared on our show that we’re having them back on for a Second Date Up...

Second Date Update: Couch Crush

23 Apr 2025

Contributed by Lukas

Our listener met a good looking lady at a FURNITURE store of all places. You don’t hear that one too often! We’ll share his story in a bra...

Awkward Tuesday: In Greg We Trust

22 Apr 2025

Contributed by Lukas

Our listeners love dysfunctional relationships so much, we didn't wanna deprive you. Here's a segment from our Full Show feed, 'Brooke and Jeffrey', &...

Second Date Update: Car Talk

21 Apr 2025

Contributed by Lukas

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 behi...

Closure Call: Switch Sitch

20 Apr 2025

Contributed by Lukas

We've got a special new episode you this weekend! It all started with a SHOCKING and mysterious Facebook message... Now, after a full year of trying t...

Second Date Update Classic: Scooby Dooby Eww A Honda Civic

19 Apr 2025

Contributed by Lukas

One of our listeners came up with the perfect first date question. You might want to steal this one once you hear it!  Get your 2nd Date Update M...

Second Date Update: Wax On Date Off

18 Apr 2025

Contributed by Lukas

The guy in today’s Second Date was so smooth with his pickup line that it impressed all of us in studio. He made the first move but can we help ...

Second Date Update: The Good, the Bad & the Fugly

16 Apr 2025

Contributed by Lukas

The woman in today’s Second Date says she waits 30 DAYS before meeting up with a guy for the second time. You’ll never believe her reasons...

Awkward Tuesday: 15 Minutes of Gurt

15 Apr 2025

Contributed by Lukas

Our listeners love dysfunctional relationships so much, we didn't wanna deprive you. Here's a segment from our Full Show feed, 'Brooke and Jeffrey', &...

Second Date Update: Fifteen Minutes of Shame

14 Apr 2025

Contributed by Lukas

The guy in today’s Second Date is sorta famous and never told us! Not until we got a hold of his date was his true identity revealed and it left...

Textual Healing: Let's Get This Goat Show On The Road

13 Apr 2025

Contributed by Lukas

We've got a special new episode you this weekend! One of our listeners is worried she may be caught in a scary situation after she was ACCIDENTALLY ad...

Second Date Update Classic: Bats on the Beach

12 Apr 2025

Contributed by Lukas

The guy in today’s Second Date Update said he tangled tongues at a very awkward time right in the middle of his date, and he DIDN’T initia...

Second Date Update: That Name Sounds Familiar

11 Apr 2025

Contributed by Lukas

For SURE, the most ANNOYING part of dating apps….. is all the wasted energy you put in, getting to know someone really ONE… Only to neve...

Second Date Update: Pre-Block

09 Apr 2025

Contributed by Lukas

Normally, Second Date Updates focus on what happened DURING the date, but today it’s all about what happened one hour AFTER the date. It left on...

Awkward Tuesday: Bonjour Betrayal

08 Apr 2025

Contributed by Lukas

Our listeners love dysfunctional relationships so much, we didn't wanna deprive you. Here's a segment from our Full Show feed, 'Brooke and Jeffrey', &...

Second Date Update: Age Is Just A Bummer

07 Apr 2025

Contributed by Lukas

Imagine being on a date and the server points out your BIGGEST insecurity… It happened to one of our listeners and you can hear what it was com...

Say Yes To The Ex: Exes Have Layers

06 Apr 2025

Contributed by Lukas

We've got a special new episode you this weekend! If there’s one thing we know, its that guys who do character impressions get ALL the ladies. O...

Second Date Update Classic: Dino Drunkfest

05 Apr 2025

Contributed by Lukas

Today’s Second Date Update is all about the 3 D’s – Dinosaurs, drinking and diamonds. Hear the call for yourself in the podcast! Get...

Second Date Update: 3rd Times A Yawn

04 Apr 2025

Contributed by Lukas

The guy on the phone today told us he’s fed up with being friend-zoned, and he wants to get ahead of things with a bizarre new plan we’ve ...

Second Date Update: Eyes Closed Mouth Open

02 Apr 2025

Contributed by Lukas

There’s one moment in every date where you can end on a high note, or push your luck and risk it all. One of our listeners says he definitely ma...

Awkward Tuesday: A.I Fail

01 Apr 2025

Contributed by Lukas

Our listeners love dysfunctional relationships so much, we didn't wanna deprive you. Here's a segment from our Full Show feed, 'Brooke and Jeffrey', &...

Second Date Update: High Stakes Higher Stacks

31 Mar 2025

Contributed by Lukas

There’s one thing a guy can put on his dating profile that will instantly UP his chances of matching by 90%... The woman on the phone today saw ...

Closure Call: Case of the Missing Roommate

30 Mar 2025

Contributed by Lukas

We've got a special new episode you this weekend! The guy on the phone today had a really close relationship with his roommate, but one fateful day fo...

Second Date Update Classic: Cowboy Confusion

29 Mar 2025

Contributed by Lukas

One of our listeners said she made the first move and left her comfort zone to hit on a handsome guy. That decision lead her here but maybe we can hel...

Second Date Update: Don't Take Me Out To The Ballgame

28 Mar 2025

Contributed by Lukas

The guy in today’s Second Date Update made a BOLD REQUEST before we even called his date. Was it fair? Sure! Was Brooke offended by it? Yep! Get...

Second Date Update UPDATE: Carjitsu Crazy

27 Mar 2025

Contributed by Lukas

Its not easy to date a pro athlete, it’s even harder when it’s an athlete from an obscure sport! One of our listeners is facing that obsta...

Second Date Update: The Rudy Of Dating

26 Mar 2025

Contributed by Lukas

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 play...

Awkward Tuesday: I Quit For You

25 Mar 2025

Contributed by Lukas

Our listeners love dysfunctional relationships so much, we didn't wanna deprive you. Here's a segment from our Full Show feed, 'Brooke and Jeffrey', &...

Second Date Update: Be Excellent and Be Thirsty

24 Mar 2025

Contributed by Lukas

One of our listeners had not one but TWO opportunities to be a “Knight In Shining Armor” for his date… so why is she ignoring him a...

Textual Healing: Hot Teacher Nick

23 Mar 2025

Contributed by Lukas

We've got a special new episode you this weekend! One of our listeners is THINKING of crossing into the forbidden love zone… but before this ch...

Second Date Update Classic: Hot Date Hijack

22 Mar 2025

Contributed by Lukas

What started as a romantic one on one date ended with our listener sandwiched between three gorgeous women all night! He’ll explain how he did i...

Second Date Update: After Date Double Trouble

21 Mar 2025

Contributed by Lukas

One person almost ended up in tears just 9 holes into a mini-golf date. No one got hit by a flying ball but our listener says it’s all his fault...

Second Date Update: Phone Paux

19 Mar 2025

Contributed by Lukas

One of our listeners became best friends with a fellow gym-goer before he decided to ask her on a date… You’ll hear how he did it in your...

Awkward Tuesday: Worst Best Man

18 Mar 2025

Contributed by Lukas

Our listeners love dysfunctional relationships so much, we didn't wanna deprive you. Here's a segment from our Full Show feed, 'Brooke and Jeffrey', &...

Second Date Update: Beauty and the Meh

17 Mar 2025

Contributed by Lukas

The guy on the phone today managed to pull a woman out of his league, and it's all thanks to ONE move he pulled at the very end of the date...Hear for...

Blind Love Is? Fluent in Flirting

16 Mar 2025

Contributed by Lukas

We've got a special new episode you this weekend! Two of our listeners are going to test the waters & see if they connect romantically when they s...

Second Date Update Classic: Whack Beach Wedding

15 Mar 2025

Contributed by Lukas

You have to take risks if you want to find true love! One of our listeners did exactly that when he crashed a strangers wedding! Hear what other dange...

Second Date Update: Offline and Oblivious

14 Mar 2025

Contributed by Lukas

The guy in today’s Second Date Update DID NOT google his date before meeting up with her and he sure wishes he did now! She’ll reveal her ...

Second Date Update: Pop Some Tags

12 Mar 2025

Contributed by Lukas

A little drawing on a cocktail napkin didn’t go the way one listener planned, and neither did his date! You’ll understand why in the Secon...

Awkward Tuesday: Ruin A Birthday

11 Mar 2025

Contributed by Lukas

Our listeners love dysfunctional relationships so much, we didn't wanna deprive you. Here's a segment from our Full Show feed, 'Brooke and Jeffrey', &...

Second Date Update: Taco Truckstop Mystery

10 Mar 2025

Contributed by Lukas

A listener from one of the most popular Second Date Updates of last year is BACK… the bad news is the guy she went out with is trying to avoid ...

Second Date Update Classic: Secret Mission

08 Mar 2025

Contributed by Lukas

One of our listeners was DITCHED on a date in a BRAZEN way and so today we’re on the hunt for ANSWERS in your Second Date Update podcast! Get yo...

Second Date Update: Dragon Thumbs and Aroma Chums

07 Mar 2025

Contributed by Lukas

One of our listeners made her date laugh so hard that something embarrassing slipped out and she’s worried it’s the reason he’s not ...

Say Yes To The Ex: Frat Man's Last Stand

06 Mar 2025

Contributed by Lukas

We've got a special episode for you today! We’re trying to get one more shot, for a guy who is desperate to win back the woman who dumped h...

Second Date Update: Give Him The Golden

05 Mar 2025

Contributed by Lukas

One of our listeners made a BIG ASK, a request we never heard before… telling a guy if he wanted any shot at dating her he had to do THIS first...

Awkward Tuesday: He Saw What He Saw

04 Mar 2025

Contributed by Lukas

Our listeners love dysfunctional relationships so much, we didn't wanna deprive you. Here's a segment from our Full Show feed, 'Brooke and Jeffrey',&n...

Second Date Update: First Date Redate

03 Mar 2025

Contributed by Lukas

Get your 2nd Date Update Merch For A Cause HERE! The guy in today’s Second Date Update has been on the show before, but today he gets the s...

Second Date Update Classic: Incriminating News At 11

01 Mar 2025

Contributed by Lukas

One of our listeners got their 15 seconds of fame DURING A DATE and it included tv cameras recording EVERYTHING he said… Find out the reason WH...

Second Date Update: Red Flaggy Much?

28 Feb 2025

Contributed by Lukas

Get your 2nd Date Update Merch For A Cause HERE! One of our listeners said he made a restaurant faux pas RIGHT AWAY on his date before he even pu...

Second Date Update UPDATE: We Built This Thing Together

27 Feb 2025

Contributed by Lukas

Get your 2nd Date Update Merch For A Cause HERE! Not everyone is wired to be ultra-romantic… that was an issue for one of our listeners mo...

Second Date Update: Love On The Rocks

26 Feb 2025

Contributed by Lukas

Get your 2nd Date Update Merch For A Cause HERE! One of our listeners helped her date survive an actual EMERGENCY on the side of a mountain. Hear...

Awkward Tuesday: I Don't Love My Boss

25 Feb 2025

Contributed by Lukas

Our listeners love dysfunctional relationships so much, we didn't wanna deprive you. Here's a segment from our Full Show feed that may have even more ...

Second Date Update: Date Night Detour

24 Feb 2025

Contributed by Lukas

If you asked a million people if they thought the surprise one of our listeners had for the woman he was dating was a good idea, NOBODY would say &ldq...

Awkward Tuesday: There's Something About Maya

23 Feb 2025

Contributed by Lukas

Our listeners love dysfunctional relationships so much, we didn't wanna deprive you. Here's a segment from our Full Show feed that may have even more ...

Second Date Update Classic: Soulmate Psychic

22 Feb 2025

Contributed by Lukas

One of our listeners had a GREAT first encounter with his date, but it was his FIRST TEXT after it ended that wrecked things… Hear what he sent...

Second Date Update: Brunette Has A Nice Ring To It

21 Feb 2025

Contributed by Lukas

One of our listeners received one of the lamest pickup lines of all time… and went along with it! It ended her up here for a Second Date Update...

Second Date Update: First Time Tinderer

19 Feb 2025

Contributed by Lukas

The woman in today’s Second Date Update is trying online dating for the first time after leaving a long term relationship. Her first try went so...

Second Date Update: Hockey Fan Gets Hosed

17 Feb 2025

Contributed by Lukas

Something caused the woman in today’s Second Date Update to abandon her date during the middle of an overtime hockey game. What was she running ...

Awkward Tuesday: Cut, Color & Flirt

16 Feb 2025

Contributed by Lukas

Our listeners love dysfunctional relationships so much, we didn't wanna deprive you. Here's a segment from our Full Show feed that may have even more ...