Brooke and Jeffrey
Second Date Update Classics: 10 Pin Mixup + Pop Goes the Relationship
25 Oct 2025
Chapter 1: What is the main topic discussed in this episode?
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Chapter 2: How far would you go for a date?
So you made a pros and cons list for each one? Pros and cons list for each one. Yeah, you can't just make a pros and cons list for one. You got to do the whole thing. Make it fair. So who got the most pros? So Hannah did. Okay. Okay, Hannah won. Oh, the original. I mean, what is duh? Like, just even the way you've been talking about it, right? Okay, yeah. I feel like the list had one thing on it.
Potter. Yeah. Okay. So did you end up actually meeting up with Hannah finally? So we ended up going bowling. Good. And we had a good time. We would cheer each other on, and we made up, like, little jokey cheers for each other as we went. Okay, so super flirty. Yeah, and when one of us would make a good shot, we'd, like, tap bowling balls.
wow yeah okay that's funny though because it's corny to us but if as long as you two are having fun yeah yeah same wavelength beers i'm sure helps yeah that's true don't get me wrong it was corny to us too like we're not immune to the fact that it was very very corny yeah yeah all right okay that's why it's fun having a great time exactly
So, but somewhere in the night, her mood changed all of a sudden, you know, I was like, what's wrong? And then she's like, nothing. I just, I think they cleaned these shoes wrong or something. Cause my feet are all itchy all of a sudden. I would go with they didn't clean them if that was the case. I hope not.
I felt like mine were clean. So I'm hoping they cleaned them, but I don't know.
She was really weird about it. Or it couldn't have been like a line because sometimes women are like, oh, I need to get out of this itchy sweater. Come rub my feet.
Yeah. Is that not the case?
In the middle of a bowling alley? Yeah, maybe not. You can't think of it like what else could have changed her mood? Like, did you do something, say something? I don't think so. Okay. I was throwing out suggestions. I was like, well, let's get you some new sewers. Maybe they did clean them wrong. And she's like, no, no, no. I just got to go. Oh. So she, you know, started packing up to leave.
But I stuck around because we'd only been going about 40 minutes at that point. And I paid for a full hour. You didn't walk her out and leave with her? No. Oh, no. Oh. I asked her one time, I was like, do you want me to come with you? And she was like, no. But like, if you want to, that's cool. But like, no. That means yes. That means yes, yes, yes, yes. That girl says if you want to, maybe.
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Chapter 3: What embarrassing challenge did a listener face on air?
Well, that definitely went onto your cons list that she made for you. That's very true, Jim. We should ask what else is on it when we come back. We'll call Hannah and try and get you a second date update right after this, okay? All right, guys, thanks. All right, hold on. Second date update. Quick recap of the events of Connor's date night with Hannah.
There was bowling, laughter, inside jokes, Hannah's itchy feet, shoe problem? She leaves, Connor stays to get his money's worth. No communication since. Connor, did I miss anything from that lightning fast recap? Yeah, no, I think you got it all. Okay. All right. Feeling good. Now, have you heard from Amy, the other girl? I'm just wondering if you have a backup, if this doesn't work out. No.
Okay. We probably shouldn't mention to Hannah that we do have a backup girl in case she says no. No, no, no. I wasn't going to say anything. I just didn't know how much pressure we had on ourselves for making this successful with Hannah. Yeah. And I'm sure there's like seven or eight backups in reality that Connor isn't telling us about. Yeah, we're all very wanted. He's a man in demand. I see.
Yeah. But none of that will come up when we call Hannah right now. You ready to do this, ma'am? We'll just talk about her possible foot fungus issue from the, you know, shoes. We should ask to make sure she's okay. Ask for her itchy feet. Okay. Connor, you ready? I'm ready. Thank you. All right, us two. Here we go. Good luck to everyone. Hello? Hey, is this Hannah?
This is she. Who's this?
Hey, my name is Jeff. I'm a radio host on a show called Brooke and Jeffrey in the Morning. Hey, Hannah. We're all here. Hey, good morning. I know you guys. Yeah. What's going on? Are you guys pranking me or something? Isn't it weird so many people ask that? Yeah. Yeah, we do.
I'm glad you have this positive energy because we do want to ask you about I guess a little bit of an unfortunate date that we heard you went on recently with a guy named Connor and
Oh, God.
Yeah.
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Chapter 4: What happened when Connor asked Hannah out?
Well, you know, dating's hard, and he had a decision to make on who he wanted to spend his time with. You won. You have a lot of pros. You know, he's like a methodical person. Like, methodical people do that type of thing, you know? Can we ask why you were offended by it? cons. Oh, we're concentrating on the cons. No one wants to read your own cons.
I know.
That's wrong. Even if you know what it is. Yeah. And it's like you can have ten compliments and one negative and you're going to remember the negative. Please tell me the con was like way too pretty, way too smart. What types of stuff did he write?
The cons were like forced
smile and not as attractive as the other girl i'm talking to oh god okay uh here's a con is right jose yeah hannah you know that that's connor on the other line he's been listening to this It's just haunting him really badly right now. Connor, did you not notice that a list was missing from your pocket when it fell out? I didn't. I didn't even know it was in my pocket.
I honestly, I'm super embarrassed because I didn't mean for you to see that. Yeah, obviously. You should have had it in the first place. Like what? That's weird. Hang on. But here's the thing. That list wasn't about you. What? What? No, no, no. I had started talking to this other girl because it took so long for you to get back to me.
You remember how there was, like, that long, like, gap between when I asked you out and you finally said yes?
I was traveling. I think I told you that.
I know that now, but I thought you just ghosted me at the end. So, like, I made this list to decide which one of the two of you to go out with, and you actually, you won. That was, that's the, that's the conflict. For her. Oh. That list was about the other girl? Not about Hannah? You're the cute one, not her. Hannah, he did tell us about the other girl. Her name was Amy. He told us all about her.
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Chapter 5: How did Connor's date with Hannah unfold?
Miami, maybe.
Okay, well.
It was my grandfather's and then.
Yeah, Brooke was right. This is like freaking Apple or something. Tiny shack in Maine on the beach nearby. But look, we're running out of time. Yeah, sure. We're running out of time here. We got to ask you, Hannah. And before we even ask, like, clearly that list shouldn't make that big of a deal because he chose you despite all of these things. And he never thought you were going to see that list.
I mean, he's so much worse.
Yeah, he would love.
He sounds pretty earnest. Would love to go out with you one more time and prove himself and we'll pay for that date.
really would i mean connor's super he's very nice and very sweet but i have two words and that's hell no really okay do you have any like friends from a wealthy family that maybe it may be cousins yeah it'll take anybody brooke and jeffrey in the morning oh that might be my biggest regret of the entire year right there not getting him a date yeah not getting her to say yes Oh, man.
She was going to say no even before she asked for the cons list. I think she just wanted to hear them. She said she was having fun. It's just I'm thinking how cool would it have been to do a second date update update with an adjusted pros and cons list. Oh, yeah. Could have heard hers that she makes about him. Actually, this is a great idea for a date night.
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Chapter 6: What unexpected issue arose during the date?
Write it up, do it on separate pieces of paper, scatter them all across the table. And then you take turns picking up one pro or one con and reading them out loud. Oh, your kids could read them out loud for you.
Oh, that's cute.
Get the whole family involved. We're going to go with a hot no. Con isn't willing to work with her family. Oh, well, I think it could be romantic. You should give it a shot. You should also give us a shot. If you need some help getting a hold of that person who isn't calling you back, we'll call them for you.
Brooke and Jeffrey in the morning.
In the dating world, we tend to put a lot of importance on the first kiss. Well, we do, actually. Tells you a lot, right? It's kind of a big deal. It could tell you everything you need to know about your chemistry together, where things might be headed between you two. Confirm, yes, she likes me.
She's touching my lips.
This is a pretty good hint.
Things are going well.
It could be a great thing. But one of our listeners was a little surprised, to say the least, by what his date said to him right after they locked lips at the end of the night. And spoiler, it wasn't, wow, that was so amazing. I can't wait to see you again so that we could do that more. Oh, shocking. It probably wouldn't be on our show then. Yeah, it's usually what people say afterwards.
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Chapter 7: What was the reaction to Connor's pros and cons list?
Do any of the other two guys pretend to hug you through the phone, Elizabeth, while giving you compliments? I don't think so.
Uh-uh. Well, I don't know if those guys are as weird as he is, but you're right.
No one's done that. I think the word you were going for was sweet there. Weird can be good. Yeah. Weird can be fun. Would it make you feel better if maybe Jeff and I hugged for you? That's just Jose really desperate for like a hug. I haven't had a hug in a long time. It's also his love language. We just want to help. Come on. You guys should go out again. One more time.
See if he can move up to number two. Yeah. I bet Nick would be a really good boyfriend. Again, she doesn't want that. A really good guy to date. Okay. One of many. Amended. Yeah, I don't think so. Sorry. All right. If it's about like... Not knowing if I'm good enough. You talk about dating other people. I've dated other people. I give you references with my exes. No, no, no.
Don't do references, bro. Actually, I would like that. No, Jeff.
Let's do that.
Let's call some of Nick's exes on the line right now and have them sing Nick's praises. I'm down. Let's do it. No, Nick. You don't want that. I don't think you want to know what your exes are really going to say about you, buddy.
Please, Nick. You don't need to do that. You don't need to do it anymore. Yeah.
I don't want to give up. How about I send you something? What's your address? I can send you an edible arrangement. What's your address? Nobody wants edible fruit as a flower arrangement.
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