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Brooke and Jeffrey: Second Date Update

Second Date Update: The Set Up

Montag, 2. November 2026 · 19 min

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Meghan told herself she’d only go out for “one drink” but that night spiraled out of control and now she needs OUR HELP to fix her mistakes in your Second Date Update!
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All right, brand new episode today.

Oh wait, maybe I should talk lower. Are people still hungover from the weekend?

Yeah, but we did get an extra hour to fight the hangover.

That's true.

So we should be normal.

Well, not all states. That's right.

Oh my God.

Or countries. Yeah, or countries.

Yeah, we do a weird thing here if you're listening in a different country where we set the clocks back an hour.

Someone in the Philippines is like, why are they off today?

So, welcome to it, and thank you so.

Much for all the love and the comments on our Halloween show.

Yes! What a fun week, guys. We had so many, I don't even know where to start with comments.

I was telling Brooke, it's like, We got, Brooke is enjoying this a little too much.

Not true. Brooke's enthusiasm. Brooke is all in. Brooke was great.

You were such a highlight, Brooke.

I have a sad hangover after Halloween. It's not an alcohol hangover. It's like, it's over.

Yeah.

And it makes me so sad. I know.

It feels fast this year.

October's such a good month.

It is.

It's so good. But hey, it's the eating month this month. And I can get into that too.

You were eating candy all month last month.

Now I'm eating more savory things.

Oh, great.

Yeah. All right, so let's get into it. Your brand new second date episode starts right now.

Brooke and Jeffrey in the morning.

Second date update.

Do you believe in second chances?

Yeah, for sure.

Like when your surgeon says, this time I promise I'll remember which kidney. You can trust me. What was a 50-50?

There's only one left now.

Still, I don't know if I would trust him. But one of our listeners, Megan, is hoping for a second chance after her date. because she says she's the one who messed up. Oh, we've heard that before. We've definitely heard about some pretty bad dates on this show in the past, but this one might be the worst yet.

What?

That is a wild claim. Can she hear us right now saying this?

Yes.

I hope she can. Megan, are you there?

I'm here.

Hello.

Would you agree with his assessment?

Yeah, how does that make you feel? Oh, 100%.

This whole thing was my fault.

Okay, good. No way.

I hope by the end of this, we can crown you as the worst dater we've ever spoken to on the show before. You have heard our show, and you are claiming this is worse than anything you've heard on the show.

Honestly, yeah.

Okay.

Oh, wow. I love it.

Let me guess.

Alcohol was involved.

Yeah. Oh, definitely. All right.

Beautiful. I love where we're going. Tell us all about this guy and how you met and how you messed up.

Okay.

So, from the beginning, I met this guy online. He's incredibly nice, very sweet.

What's his name?

So.

His name is Richard.

Okay.

He asked me out to dinner.

Okay.

Nice.

It was a Friday night.

It was 8 o'clock, whatever, so.

Okay, he gave you prime time. I was going to say.

Yeah.

Prime time for dating.

So it seems.

But so what happened was I got out of work at five. I was with some of my girls.

They wanted to go to happy hour.

And I was just like, okay, I can pregame a little bit before this date.

Just like settle the nerves kind of thing. I'll have a drink, whatever.

Yeah. What's one flight of tequila before a date? Like, that's fine.

Yeah.

And it is always those nights that you do not have one.

Yeah.

Okay.

So what happens? You're at happy hour with your girls.

I got... so wasted i lost track of time oh yeah i was obliterated like i i wouldn't i would tell you then that i was.

Fine and your girlfriends who are there with you they're not discouraging you from going and meeting up with this guy after all the.

Drinking oh i was hoping you were so late you forgot Well, okay.

So what happened was I look at the clock. I'm like, oh my God, it's like nine o'clock. So I realized this.

I immediately like.

Sober up for 20 seconds.

My friends are like, oh, see if he's still there.

Like whatever.

So I'm like, okay.

And I pay my tab. And I go to this place an hour and 20 minutes late and he's sitting there.

No!

He's waiting for you?

Yep.

Wow.

That's the worst case scenario.

Oh, he is a nice guy.

I'm thinking you just showed up so you could say, I tried. I'm just like, I'm so sorry.

I'm a mess.

I lost track of time.

Like, whatever.

He... And he was just like, yeah, let's just.

Eat, like, whatever.

And he forgave me, like, immediately.

And I was like, oh, amazing, because I am so hungry.

Okay.

So does the night get better from here, or does it get worse?

Oh, not, no, not great.

So I proceed to, I think, order, like... Seven things off the menu.

Please tell me the server was like, no. You're going to get two things maybe.

No, the server's probably like, yeah, you need it.

Yeah.

And this whole thing happens after I rush in an hour and 20 minutes late and bump into the table and spill his entire glass of red wine all over him.

Oh, no.

Yeah.

And then they bring out the food, and I start eating, and obviously I don't feel great.

No.

Uh-oh.

Uh-oh. I stand up to go to the bathroom.

Oh.

Okay.

He's got a plate of pasta in front of him.

No, you do not do what I think you did.

Oh, yeah.

Red sauce all over the place on top of the red wine.

Oh, you spilled it.

I thought you were nauseous.

Yeah.

No, no, no, no.

So you're just like tripping everywhere. Yeah.

I cannot stand guys.

Oh, my God.

What does he say at this point? Like, let me get you an Uber. You need to go home. Not even he's so nice.

Like, we had most of our food at that point because I ordered 17 things.

And he's just like, oh, no problem.

Like, whatever.

Just, like, go to the bathroom.

Take a minute.

Like, this whole thing. And I was like, oh, my God. Mortified.

Well, that is what a nice guy would do. He would be patient with you and finish the date and then just never talk to you again.

I could get you out of there ASAP. Yeah.

So what happens when you finally get out and you go rejoin Richard? When I finally get out, which could be.

An hour to a day later, who knows.

He had paid for the entire bill and left.

What a gentleman.

That is nice.

He paid.

He didn't need to.

Please tell me you didn't also text or call him while still drunk that night.

I actually did. But luckily for him, he did not pick up.

Lucky for you.

Yeah.

So I just want to apologize.

I made such a mess.

It was just worst date ever. And he was such a nice guy. And like, if it were me, I would never have paid for that bill.

I bet your girlfriends are just like, girl, what did you do?

Maybe if we get him on the phone, you need to offer to take him to dinner.

Yes.

Don't even give a gift card. Like, you owe him, Carla.

Oh, absolutely. I feel like, at this point, I feel so guilty that I would, like, offer to pay for his dinner with, like, someone else.

Well, that's great.

On a date with someone else.

Yeah.

Perfect. That takes all the pressure off of us.

Aw, I like this.

When we come back, we can reach out to Richard. Hopefully he picks up and you can apologize for what has been one of the worst dates we've ever heard of on our show. It's pretty bad to start.

I'm sure he's told all of his friends, too, about what happened.

We'll see what he has to say when we come back and do your second date update right after this. Hold on.

Brooke and Jeffrey in the morning. Second date update.

Text in to 78592. Do you think this is one of the worst dating disaster stories that you have heard on our show? Because I'll try to quickly list off all the mistakes that Megan said she made that night. One. Pre-partied way too much and showed up an hour and 20 minutes late completely wasted.

Yeah, that was the biggest one.

Then immediately bumped the table and spilled a full glass of red wine onto her date Richard's lap, followed by a full plate of pasta.

Mind you, he was still wearing his work clothes, so they were expensive stuff he had on.

And then she rushed to the bathroom. where she stayed for who knows how long. She doesn't remember. By the time she finally reemerged, Richard was gone after he'd paid... hundreds of dollars for all of the food she had ordered before the bathroom.

Seven plates?

Something like that. Okay, hold on. She keeps saying seven. She was wasted, guys. It could have been three.

It's true.

If she did not take the leftovers home, I'm disappointed in.

Her.

I mean, you can still be drunk girl smart, okay?

But then the final cherry on top, she tried drunk dialing him later that night, which thankfully he didn't answer. And that brings us to here.

Yay!

Being on the radio, you're absolute rock bottom.

Are you still hungover?

I'm not hungover, but I really need to apologize to him.

I like that stop of mine for you. Okay, and so before we call him, I wasn't clear with the first part. You said you didn't even want to redo with him, right? You said you just wanted to apologize and send him out with someone else?

I mean, I, yeah, I was being generous, but like, I obviously would love to see him again if he doesn't want to though. Like there's no argument.

I can't imagine why he wouldn't, but okay.

I'm sure I could still argue with him actually on that point. So I got you.

Well, let's see if he will even answer the phone for us. Cause I'm going to dial his number and we'll see how this goes.

Okay.

Hello?

Oh, hey. Sorry, is this Richard?

Yeah, who's this?

Hi, Richard.

Hey, man. Hey, good morning.

This is a radio show called Brooke and Jeffrey in the Morning.

Did I win something?

Hey, maybe.

Kind of.

Yeah, I don't know about that. You won in love. I don't know about that either, Brooke.

What?

I don't know.

How many people are there?

I swear I'm sober.

Yeah, Brooke, don't ruin this. Good morning. Hey, there's four of us here. There's a lot.

Okay. What's going on?

We're doing a segment on our show. It's called The Second Date Update. Basically, we're trying to get in touch with you on behalf of one of our listeners named Megan, who you went on a date with the other night.

Yeah.

You remember?

This one's a little different for us, too, because.

We know why. Yeah. We heard it may not have been like a totally flawless date. Yeah.

That was an unfortunate night.

Yeah.

That's how Megan actually phrased it, too. Yeah, okay. More than unfortunate. Disaster. Yeah, she knows that she messed up pretty bad.

Dude, I don't fully trust all of what Megan told us about the date because it doesn't sound like she probably even remembers everything.

Yeah, well, I kind of feel like she's not normally like that. I kind of feel bad for her, honestly.

Aww.

Well, you'd hope most people. That's so nice.

Yeah.

Obviously, she overdid it that night.

I mean, but some people, like, she's really a stranger to you. Some people would be angry that she wasted your time.

Oh, yeah.

You know, that's like a kind way to look at it.

That's true.

You could feel disrespected.

Yeah. I feel like I did the best I could. And, you know, I feel sorry for her, but I'm not, I don't need that kind of drama in my life.

Well, I mean.

I wish her the best of luck, but that's not something I want in my life.

You mean just like the drunk girl energy drama? Babysitting?

Uh-huh.

A hundred percent.

You're like, that was on the first date. That's the first impression she's giving away.

That's true. That makes sense, I guess. But Everybody makes bonehead mistakes when they're on dates sometimes, but let's forget about those. Go back to the very beginning when you first met her. Do you remember what you liked about Megan? What attracted you to her initially?

You mean before she walked in the restaurant?

Yeah. And spill all the wine all over your lap. We heard about that.

Forget about that. Let's go back to before. Tell us about that.

I don't know. She seems like fun and like, she's like a lover of life. You know, I'm attracted to her, but.

Good.

Let's keep that energy going.

Okay.

Yeah.

That's a pretty nice one already.

Yeah.

What are you guys doing? What's going on?

Well, I'm just saying, like, if there was a good connection, good vibes at the start, and then a sincere apology came in on top, that would feel pretty good to hear, I imagine. Right, Richard?

I guess, yeah. I mean, and you.

Always want to be with someone that can admit when they're wrong.

I mean, she was wrong.

Yeah.

Jeff can admit it.

It's so many ways.

I'm going to go out on a limb and say that.

Yeah.

Way to be vulnerable, Jeff. I know.

That's big of me to do, but it's even bigger of Megan to do it because I don't know if you realize this, Richard. She's on the phone with us right now waiting to.

Apologize to you.

Hi, Richard.

Hi.

Yeah.

I don't have a lot to say.

Except don't f * * * ing ghost people.

What?

What?

You being got?

You were got.

Do you remember a girl named Annie?

Wait, who?

Hold on.

Wait, wait, wait.

What? What do you mean got?

Richard.

Richard, do you remember a girl named Annie? What are you talking about?

You went on a date with her like a couple months ago, and then you ghosted her. What? Yeah, that was my sister.

Oh.

Wait.

Oh my God. Wait, hold up.

This is like a weird revenge for him ghosting your sister.

Richard, you didn't recognize it was her sister?

No.

What?

I mean, some sisters look really different. Why'd you ghost her, Richard?

Wait.

I didn't feel the vibe. What is, how old are we?

You didn't?

You didn't feel the, that's how people say they're not interested.

They just don't respond. This is revenge?

This is sick.

Wait, did you actually go on a date with Richard? Did you purposely get drunk?

100%.

Oh!

Wait, Megan, you didn't mention any of this to us. No, because why would I?

You never would have told me.

Yeah, there's a reason we wouldn't have done it, because this is wrong.

Why is that wrong?

If you want to talk about being an adult, you would have called my sister and you would have told her that it's not working out.

You had a nice date and you walked away. You broke her heart. She gave me creepy vibes and now I know where she runs the family apparently.

She gave you creepy vibes.

That's hilarious.

Joke's on you because you paid a $ 500 bill to.

A girl who showed up.

That's why you ordered all those Trace, you knew what you were doing. It all makes sense. Jeez, Megan. Oh my God.

Megan, how could hurt your sister's heart be broken after like a date or two with some dude?

She was down and out.

She was putting herself out there for the first time in a while.

She had a horrible breakup and you just.

Confirmed for her that there's no point in dating. Thank you very much because men are trash.

Men are trash. You spilled wine on him and pasta and ordered all those things and he still took care of you the whole night. Yeah.

And you know what?

I loved every.

Bit of it.

I feel like this is just like some vicious circle that men and women are going to do until eternity if we keep.

Acting like this. That's why you've got to just stop dating. Everyone listening, just stop it.

Honestly, that's how I feel right now. I don't ever want to go on a date again. Oh, no. You don't have to go on a date again. Two sisters back to back, and this is what happens.

This is crazy, guys.

I always say that sister fantasy is way overrated.

No, no one was.

Okay. Hold on.

Can we let the dust settle?

Yeah.

I can't even comprehend this right now. And Richard, we did not know that this is why Megan was calling us to reach out to you. I don't know.

Honestly, I don't know who to believe anymore.

Shouldn't we be asking why you ghosted her sister?

I wasn't into her. It's really simple.

Then why did you hook up with her?

Oh, no, brother. Yeah, that's not a good look on you.

You hooked up with her and ghosted her? Maybe she wasn't very good.

Okay. That doesn't matter. I didn't say it.

I didn't say it. Oh, wow.

This is awful, though.

That's mean.

This has really gone off the rails. I thought we were starting to go towards, like, we're going to apologize and have a forgiveness thing. This nice guy who stood up for a girl one night, but it turns out to be a huge big plot to get revenge for a sister that got ghosted.

And we helped!

But incredible that you were able to get so drunk and stay with the plot.

That is true. That's very impressive. I would have lost it.

You're giving her credit? What is happening?

I mean, honestly, you guys aren't that different of people. I mean, you're ghosting people. She's getting revenge.

I don't know.

Maybe they are perfect for each other.

I know this is kind of crazy, Richard, but we'd love to send you and Megan out.

One more time.

Hell no. Fine, you and Annie then, her sister. She sounds like she's still hurt.

No.

No, you are not calling my sister ever again.

You stay away from her.

You stay away from both of us.

Okay.

Well, this was fun. What a fun ride we've all been on.

Yeah, that was crazy.

We didn't even do anything.

So glad I picked up the phone.

Brooke and Jeffrey in the morning.

Oh, man.

I understand that feelings get hurt in the dating world. Sometimes it's ugly and it's unfair. But I feel like maybe there's a better way to handle it than planning to publicly humiliate someone over the radio.

It's just so much energy into a person that doesn't matter to your sister.

A whole Friday night. Oh, my God.

And don't get me wrong. It's entertaining. But is it? healthy for you?

No.

When have we ever promoted healthy, Jack? Get a grip.

Or if you're going to do it, at least have us in on the plot. That way we're not humiliated and blindsided too. Yeah, but she's right. I mean, if she would have told us, we wouldn't have called her. We would have chosen this one. Yeah, and then I wouldn't have had Brooke's Carlo Rossi spilled all over my lap.

It was a whole jug.

Yeah, that was kind of a silver lining for me. And I just sat there the entire time. I didn't even move.

Those tiny little handles on those legs.

You got good wrist strength, Brooke.

Yeah, I'm impressed.

But clearly that was never going to work out, even if we had tried. But it doesn't mean it won't work for you. You can always email us, and we'll call that person who's not calling you back. Go check out all of our Second Date Update podcasts. They're up online wherever you find yours at Brooke and Jeffrey.

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