Second Date Update: Best Date of My Life

Published Jun 18, 2025, 3:14 PM

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 new Second Date Update!

Second date up date, Brooke, I want you to think about the best date that you've ever been on. I know it's probably not with your husband. Nobody here expected it would be. What's the thing that happened that made you say this date tops them all? A big question.

Honestly, it's just the person I'm with, Like, I.

Come, you're talking about yourself again. The fireworks are like the chef made me a seven snail, the three way kiss at the end. That's it. Okay, Yeah, that makes sense. One of our listeners emailed the show saying his most recent date easily ranks number one all time, and I'm just assuming he's been on more than one otherwise that statement really doesn't say much. Let's talk to Chris about it. Chris, Welcome to the show Man. How you doing.

Hey, guys, thanks for taking my call. I really appreciate it.

Yeah, like you're putting a lot of pressure on this first date.

Yeah, you have been on more than one date in your life, right, Yes.

No, I've been in a lot of dates in the last few years, and honestly, none of them really hit at all, Like I didn't feel like there was any connection. But this last girl, Kendra it was like the date of a lifetime.

Okay, why are you saying that because of Kendra or because of the activity in the environment.

I think it was a combination of the entire The huntire night was kind of great. You'll see, you'll see by the end our dad.

Lives will look paltry in comparison.

Oh yeah, yeah, let's get right into it. Tell us where'd you meet Kendra?

Okay? So I bought her flowers? We went to a restaurant.

Question that I asked her. You're really eager to tell us, and I appreciate that.

But.

So excited about this story. Where where did you meet her?

Oh?

We met online?

There understand why that.

Was an confusing question.

Yeah, I see. And now where did you two meet at a restaurant? It sounds like.

At a restaurant.

Yeah, I'm he bought her flowers, okay, And.

I bought her flowers, which is an important part of the story because she was so shocked by the guy, because no guys buy flowers anymore, That's what she said at me at least.

Oh, no guys buy flowers.

Well, they are pretty expensive. I've got in trouble. Like the girls like flowers and they like them after That is a good point, Alexis. I mean, what did Kendra do with the flowers after you gave them to her?

Well, that was part of the story. The server even complimented the flowers. When the server complimented the flowers, she offered to let the server put flowers on everyone's tables.

So she accepted your gift and immediately gave it away to the Okay.

Which, when you say it like that, it doesn't sound so good. It was really nice to watch that happen and the people happy with these flowers. It was a really nice moment.

Yeah, you bought everyone flowers.

Well, everyone in the restaurant doesn't get it.

It is a really good move, though. I feel like it looks good in her eyes, and I assume it must have led to some good conversation, to some good moments.

It really did. In fact, I'd say it got a little cheesy and so good that I got myself a little vulnerable, you know what I mean.

Oh, the plants came off that quickly.

Say it like that?

Yeah, did you say I cried?

Is that what you just said?

We didn't cry, But I'm sort of as a twenty six year old I gave up on meeting anybody at this point.

So twenty six isn't that old?

Just so you know, she's twenty nine, and she said she was going through similar stuff, so it was like we kind of hit on the same subjects.

Wow, what happened At the end of the night.

We went back to her place. We walked to her place. She didn't live that far from the restaurant, so it was a really nice romantic walk.

Did you hold hands?

We held pinkies?

That's even better.

I don't know.

That's the friend finger. Yeah, wait, you have a friend finger. Yeah, that's the one you do pinky promises with your friends. Oh, I thought you were going I thought anyway, did you after the pinky hole thing? Did you get a kiss?

So it was kind of a funny situation. She lives in a community that has a wall around it, and you have to it's not easy to get into, you know.

A biodome or a prison or some sort.

I think it's just an apartment with a gate is what you need, which are pretty common.

Okay, I like bio prison. I'm not familiar, but okay, I get it. There's a gate.

So there's a gate, and she didn't have her key, so you're locked out.

Or maybe it's a move that she's pulling where she's like, oh, I can't find my keys up.

Do you need me to strip search myself?

Maybe I was more like, maybe we should go back to your place instead.

Maybe that I don't think she.

Need to pull a move to go back to a guy. Yeah, I'm standing naked.

State. So so what happened, Chris?

I know this sounds ridiculous, but so I decided to jump the gate so.

You can open it on the other side.

Yeah. Yeah, I had to climb it and pull myself up over it. As I'm pulling myself up over it, I get stuck. My pants get stuck on it. When I get gone, I'm hanging upside down.

No spiky fences, right, Yes.

What did she do?

Well? She kissed me.

The man kiss upside down upside down.

Man, and she kissed you.

I was just as shocked as you were.

I guess she likes her mobile vulnerable.

But now I can get him pounce. Did you like it?

Like?

Was that awkward or was it romo?

Oh? No, it was a nice It's a very nice romantic moment. But it's been a couple of days. Since that happened, we texted for a couple of days, and then since then she hasn't gotten back to.

Maybe you're a man ups Yeah, it can be confusing because usually you put your tongue this way, but when you're upside down and needs to go that way.

So we found another man suspended on a fence and took.

Yeah, maybe that's her thing. Some guy working on the phone lines. Okay, well we're gonna we're gonna come back. We'll call Kendra for you and try to get you your next most romantic date ever. When we get you maybe a right side up kiss. Let's not get crazy. We'll do it with your second date update, next second date update. If you're just joining us, we've basically got the real life Peter Parker on the phone who received the rare coveted upside down kiss during his date with Kendra.

You didn't see the sequel where the Spider Man got his pantst Okay, yeah, we're.

Still in the Toby Maguire University.

Toby would totally get his pants stuck on a fee. Yeah.

It happened after Chris fell while scaling the security gate outside of Kendra's apartment, as you do a lot of dates and hard to climb, though, pants got caught when he fell, and it was there in that embarrassing moment when animal instinct took over and Kendra walked right up to him and smooched him in the face, Which.

Is such a good sign because that really could have been an ick moment for her. Yeah, you know, and obviously she thought it was.

Adorable, So no wonder Chris is describing it as his best date ever. But weird that she's not texting him back since she's the one who initiated that moment.

You know, we never asked, Chris, did she ever get back into her apartment, because maybe that's why she hasn't responded that adoint.

Yeah, somebody came by a few minutes later I let her in.

Oh okay, guys, that long I didn't even take about just waiting until somebody else showed up.

We're gonna call Kendra. We'll see if she picks up.

And God, I hope this works out for you. I mean, there's so much pressure on this one. You know, it's like his best date he's ever been on.

Well, I felt pretty relaxed until you said that. Now all of a sudden, I'm stressed out for no reason. Don't screw it up, jeff Oh god, okay, here we go.

Then, Hello, Hey is this Kendra?

Yes, she said, who is this?

Yeah?

She said, sorry, kend Yeah, we're a radio show. We're called Broken Jeffrey in the Morning.

How many?

How many of you are there?

Too many? Yes, it's a whole show, Kendra.

Okay, all right.

So we're reaching out to you because one of our listeners has asked us to get a hold of you a guy that you went on a date with recently named Chris.

Oh, okay, yeah.

So this is all part of a segment we do call the Second Date Update, where we're trying to figure out if there's a reason you have stopped texting him after the date.

I mean obviously, yeah.

Obviously the reason should be obvious.

No, no, no, just like it's obvious that yes, I have a reason.

Yeah, okay. We just want to know because we spoke to Chris and he told us about your date and it sounded actually much better than we ever thought it could have been given the circumstances.

Honestly, I'd love to hear your side of the story.

Yeah, okay, it was a good date. Like, it was a really good date, honestly, so cute.

Okay.

I mean I wouldn't have kissed him at the end of it if it was a bad dated.

That's where you and Brook differed.

But he told us about that first kiss, like that was crazy, the upside down one.

Yeah, I mean, when you have a movie moment, you have to like take it right.

Oh you felt like it was that magical too, like it really was a movie moment.

Well, yeah, it was.

A spider Man kiss.

Okay, yeah, that's the first thing we jumped to as well. Well, yeah, if that's the case, then why after your movie moment aren't you calling Chris back?

Well, I mean, I don't really know what he told you besides that we kiss, but I mean that was.

The majority we know that you guys went to a restaurant. He told us about.

The flowers that he brought you flowers, and you guys passed him out among the other tables.

Immediately gave gift away.

Oh yes, I didn't think he would mind.

So it was really sweet.

Oh okay, okay, okay, yeah, yeah, here's the thing. Chris is great, but he lied to me, and I mean he lied about something pretty big and I did.

Big, like what like his name or something?

Dude, I mean, no, it's not his name.

He said that he was twenty six and he's like, forty two is what?

Yeah? Ware again, wait a second, you had a good time. I had a good time. Why does it matter? What is anybody? Okay?

Okay, wait wait Chris, that doesn't sound good. Kendrick, you didn't know this, but Chris has been listening on the other line. Maybe yeah, my god.

That because I'm forty two. But that's all.

You are? Forty two? Chris, you told us that you were twenty six.

I'm kidding, bro.

But age doesn't matter. It doesn't matter how old I am. Again, we had a.

Good fund lie about it, so it doesn't matter.

Why do you lie?

That's only thirteen years different?

Okay, okay, that is my so long And Chris, if age isn't important, then why did you lie about it?

Because she wouldn't have woun out with me if I said I was forty two. I had.

When I was in my twenties. I wouldn't date somebody in the forties either.

Yeah, it happens in Hollywood all the time men and women are older than the significant others.

Actually normal, a lot of healthy relationships and hold.

Yaps, and it's people having the information to make that choice. Right, So she you lied to her.

Yeah, Kendre, what are your thoughts on this?

I mean, here's the thing, Like, I'm not entirely truthful my age on the apps either.

What Wait, I.

Say that I'm twenty nine, but I'm actually thirty one.

But that's not like a wait.

A second, Wait a second, you lie about your age online? That's dis shocking.

Wait okay, chancastic, you don't really have a leg to stand on. I think he's being sarcastic. You're being sarcastic, right, No.

It's the same. A lie is a lie, whether it's twenty nine or forty two.

So you're not upset that she lied about her age because you lied about yours.

I'm upset that she's upset about me lying about my age if she lies about hers.

Somehow, you think, no matter what it is, the lies should cancel out and you should be on even playing field.

Yeah, a lie should cancel out a lie.

Okay, Okay, I kind of messed up that you lied.

No, here's my thing, It's like when people are like looking for people who they want to date and they go to my age bracket. They're looking for people between thirty and forty, and I don't want to people like I'd rather use someone who's a little bit younger.

So you aged out of the age bracket you're interested in, is.

The problem, Yes, but not by sixteen years.

It's thirteen.

Yeah, it's sixteen. He doesn't know how to do math. It's literally sixteen.

But he's doing the same exact thing that you're doing. He's lying about his age to open up his options the same way that you are.

But he's opening it too far.

Yeah, okay, I mean I don't think what she's doing is right, but I can see her point, Like, you have a generation gap between somebody, Well, I guess you're thirty one now, so now you're only eleven years apart in age, So now it's not as big.

A gap billions of years old. What's the difference between thirteen years.

I can't tell who side him on him?

Yeah, and technically the age gap is just eleven years now.

Yeah, that's what I just said.

But I wasn't listening to you Brook because you're older I have my cutoff at age thirty five, So Alexis, if you have anything to say, feel free to jump in.

I'm so confused.

My question is when you kissed him, did you know he was forty by then?

I had suspicions.

I mean, I knew he wasn't twenty six.

But that means you guys got along so well, even you were bending your rules a little in your right exactly, I.

Wasn't bending my rules eleven years.

No, you're right, you are right, But I'm just saying that a point you came to a conclusion almost and.

You still I think Jose's onto something you both can you get over this? Is that that's really the question is not the only problem, because if you guys just get along, great, Just a big lie about.

That age is just a number. It shouldn't matter if the connection is real. And if that connection is true, we'd like to offer to send you to out on another date, and we would pay for it.

That would be nice. I like when people pay for my dates. I do it. I'm down, yeah, cheap.

Cheap, old man, I see waiting for that senior discount. But Kendra, we will pay for it.

It's up to you look, if we would have met organically and had the connection we had, then I might have been able to forget that he's forty two. But the lying is it's just bother.

Your lies don't bother. My life is fine, you know, Chris, I'm sorry, man, it was the best state of his entire life.

Well, if that's it, guys, I'm gonna let him know the truth that I'm not actually forty two, I'm forty six.

What is that why you wore the baseball hat backwards on our dates?

Like you're literally adapt and that's.

Why you couldn't get over the fence.

No wonder he knows who Toby maguire is. Rook Jeffrey in the morning. Man. I know this happens all the time on the dating apps now, where people lie about their age. But I don't know if I'm ever gonna understand the thinking behind it, because at some point the truth about your real age is gonna come out.

Yeah.

Well, I mean maybe it's like one of those things where you feel like you'll just be so connected by then it won't matter. Yeah, that's what you hope, right. I don't think that that's ever true. A lie always matters.

But yeah, because eventually you're gonna have to explain why your high school graduation photo has a watermark that says Sears portrait student in nineteen eighty six, and everyone's gonna be confused. I thought it was bold that he tried to play off that he was younger than her. Yeah, I'm Jesus, okay, I'm thirty two, or like, I'm a few years older. He's three years younger than her. He's overcome twenty years different.

All I need to know is what filter he's using on his photos. I need I don't need it for personal use, I swear. Yeah, it's just a curiosity got Okay.

So just to be clear, we're not saying don't lie. We're just saying lie smarter. Yeah, okay, to do that, jeff.

We're saying, don't lie.

I'll make it believable, okay.

Yeah.

If you want some help with your dating life, lies or not, email the show. We'll call that person who's not calling you back and go find out all of our second dates. They're up online wherever you get your podcasts, yea to search Brook and Jeffrey