Brooke and Jeffrey: Second Date Update - Second Date Update: Long Distance Surprise

Episode Date: January 7, 2022

What do you do if your perfect match lives 500 miles away? You fly to meet them for your first date! At least, that's what one of our listeners did...He hopped on a plane… And now he's going to hop on the phone with us, because thing didn't go how he expected....See omnystudio.com/listener for privacy information.

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You'll hear from Bloomberg journalists like Matt Levine. A lot of this meme stock stuff is, I think, embarrassing to the SEC. Follow The Big Take podcast on the iHeartRadio app, Apple Podcasts, or wherever you listen. People, my people, what's up? This is Questlove. Man, I cannot believe we're already wrapping up another season of Questlove Supreme.

Man, we've got some amazing guests lined up to close out the season, but you know, I don't want any of you guys to miss all the incredible conversations we've had so far. I mean, we talked to A. But, you know, I don't want any of you guys to miss all the incredible conversations we've had so far. I mean, we talked to A. Marie, Johnny Marr, Eve,

Jonathan Schechter, Billy Porter, and so many more. Look, if you haven't heard these episodes yet, hey, now's your chance. You gotta check them out. Listen to Questlove Supreme on the iHeartRadio app,

Apple Podcasts, or wherever you get your podcasts. Second date update. Think for a second. What do you think is the farthest you've ever traveled to go out on a first date? Oh, wow. A first date? I don't know.

One time I went all the way down to the lobby of my fifth floor apartment. Wait, that's the farthest you've gone? Yeah. They have a vending machine, a water fountain down there, cheap couch. I mean, what more do you need to have a great date? That's true. Okay. You're a simple man, Jeff.

That's right. But one of our listeners says he actually boarded a plane in order to take a woman out on their first night. And now he needs our help. So his name's Kirk. Kirk, what's your credit card number? Or no, sorry, that's not what you asked to start this segment. Kirk, how are you?

What's the person's name that you went to go see? The girl's name is Jillian. Jillian. Jillian. Wait, I have a question. Can we just know right off the bat, are you boarding the plane because you're going to see her somewhere, or are you both getting on the plane together?

No, I had boarded a plane to go see her. Okay. Oh, she lives far away. I've almost done this twice with listeners and fans from other parts, and I've never been able to pull the trigger. It's just too scary. You were going to go to England. I was going to England.

Imagine if it doesn't go well first day. Now I have a week in England or wherever. Oh, that sounds terrible. By yourself, by yourself. That would just be awful. And plus Jose flying without a chaperone on the plane.

It's just not a good idea for anybody. Good point. But Kirk, tell us more about Jillian. How'd you guys meet? Well, it was the typical online website thing and i was talking to her for like a month or so and it was weird because i started catching feelings for her like super quick yeah what do you think like what

about her so i was in a relationship for eight years prior and it was kind of like maybe a bounce back thing for me, but it was a little bit more than that. You know, I really, really started to love her. Yeah, you can rebound in your own zip code. Yeah. I mean, that's allowed. And you can do it like right after the breakup. You don't got to wait eight years.

Yeah. Did I hear you say you started to love her? What? I was beginning to fall in love with her for sure. Without even having met her yet. That's crazy, bro. I've heard that happen a lot, though. I mean, like, how often are you guys talking? Oh, we were talking, like, every night before we go to bed.

Oh, you guys were so excited to talk to each other. The chemistry, the chemistry was amazing. But the thing is that I've never video chatted her. So it was all just talking. So you may be a catfish. I don't want to say that, bro, but... Yeah, it's definitely a red flag. What was it like when you actually flew out to see her?

No, man. Let me tell you, I probably should have video chatted her. Oh, no, bro. Why? Because you needed to reveal something or what? No, no, no, no. It was just that she told me a week before I went out there that she was going to be at a hotel speaking for her job or something like that.

And I thought it would be a cool idea for me to just jump on a flight. And where she was at, I would just meet up with her. Oh, wait, as like a surprise? Yeah, I was just surprised, you know, because we've been talking. And I thought it was like something in my heart told me I could do this, you know? Oh, wow. Well, if you guys are that bonded, bro, and you feel that, I understand if you guys are kind of exclusive

and you guys know everything about each other. I mean, there's so much risk there. You have never been to this woman's hometown. She doesn't know you're coming. She's at a work event. But you actually flew out and you saw her. What was that like? I flew out there.

I went to the hotel. I blended in with the crowd. And I've never seen her before, so I didn't know what she looked like. You didn't i went to the hotel i blended in with the crowd and i you know i've never seen her before so i didn't know what she looked like you didn't even have to blend in she has no idea what you guys look like because you guys video and like what are you doing just in the crowd asking like hey you know who jillian is no i was just gonna be like waiting for them to announce her oh she's gonna go up on stage and do a talk. And then you run on stage. Jillian! It's me! I love you! That would have been so cute, right? Maybe. Not very fashionable.

Those thoughts all ran through my mind. I played it cool. I played it cool. And the thing is this. When I heard her voice, I knew it was her. And going back to what you said earlier, she wasn't who she said she was.

She didn't look anything like her. Oh. Like maybe she was using a different person in her pictures, like that much difference? Yeah. Oh. Because sometimes it's Photoshop and it's like, oh, you know. Full-blown catfish. So now you've taken a flight to go see this woman.

You're in a completely different town. What do you do? Do you stick around? Oh, man, of course I stick around, man. I had so many feelings. I was angry. I was lied to. Yeah.

So I had to speak to her. It was like, no way I was going to leave without talking to her. And I saw her and I just said, surprise. Oh. Ugh. I'm cringing just thinking about it. What is her? Did she recognize your voice right away?

She recognized my voice right away. She turned around and it was so awkward because she started crying. Oh, sweetie. Oh, no. So now I'm like from anger to like feeling bad. Yeah. I mean, she's doing it because she's like self-conscious right i mean why else would you pretend to look like somebody else well is she prettier was she just like a

way prettier or were you like holding some onions right up to her face is that what was happening it's not usually because you're a victoria's secret model in disguise after she started crying i was like man let's. So I went to the car and we started talking, told her how I felt. And I said, if you want, give me a call later on tonight. We'll have some drinks or something at the hotel. Okay. So you guys ended on a good note then. That's good.

Yeah, we ended on a good note. Just like the same connection we had when we were talking in the beginning. It kind of like filled in again. That's how you know it's real, bro. Yeah, and then we talked a few times when i got home but she really doesn't know how i feel right now you know like i said i still want to talk to her so she doesn't know that okay okay and so now we're gonna call her and let her know how you feel that's perfect man do you want to see her and uh maybe you know if

we do see each other she can fly out to see me this time. We don't have any plane tickets in the radio station's budget, though, so that's going to come from you. Oh, bus, though. We could bus her in. Oh, yeah. I mean, that's our budget. We could get a greyhound over here if you want. In two weeks, it'll be so cute. Oh, this is so cute. I'm so excited.

She flies to see you guys fall in love and have babies. We'll play a song. I'll go talk to the radio station accountant to make sure that we can finance this thing, but then we'll call Jillian for you and try and get your second date update, okay? Oh, perfect, man. Alright, hold on. Second date update. Catfished

by a woman who lives a full plane ride away. He shows up to surprise her and discovers she looks nothing like her profile pics. Oh, man. But he's still DTFIL. What is the IL?

Down to fall in love. Aww. Welcome to the life of our listener, Kirk. I'm DTFIL. Who's asking us to call Jillian today. Brooke, are you in love? I know, but I'm so excited for Kirk. I'm just so excited about this. I think Jillian's going to be over the moon when we call her. Brooke, you're already in love. I know, but I'm so excited for Kirk. I'm just so excited about

this. I think Jillian's going to be over the moon when we call her. Okay, no pressure now. Good work, Brooke. But according to your email, Kirk, the reason that you want to do this second date is because with the whole long distance thing happening, you only talked a couple times since you've been back from that trip over the last two weeks. Like, is that

worrying you? Kind of, because we used to talk every day so if you haven't told her that you are okay with like her not being the person she said she was originally you know she probably just thinks that you're still mad at her she may be still embarrassed you know yeah you know what it took me a little bit of time to process everything so i get what you're coming from dude that's valid's valid. And maybe there's a chance that she's not DTFIL. She's just DTF.

Would that be okay? That's more common. Yeah. Down to fall? Wait. What are you talking about? Actually, I don't know what I'm talking about.

But either way, I know we're all rooting for you here. Yes! I can't wait. I'm going to dial Jillian's number right now, right? All right.

All right. This is so fun. Here we go.ian's number right now right all right all right this is so fun here we go let's get the plane flight ready hello hi is this jillian speaking hey jillian my name is jeff from the radio show brooke and jeffrey. Do you have Brooke and Jeffrey in the Morning on the radio where you live? Oh, yeah. We didn't ask that. Yeah.

I'm sorry. Who is this? Hi. That's a no. Yeah, it's fine. That's all right. We're Morning Radio Show, and we're doing a segment called

The Second Date Update that we'd like you to be a part of. Well, actually, too late. You're a part of it. Yeah. Congratulations. Welcome to our show. We're really excited to talk to you, Jill a part of. Well, actually, too late. You're a part of it. Yeah. Congratulations. Welcome to our show. We're really excited to talk to you, Jillian,

or I am, anyway. Okay, well, I'm glad you're excited, but I don't know you. Okay, yeah. That's true. You don't know us, but you do know somebody that listens to our show and that asked us to call you,

and his name's Kirk. What? Yeah. Yeah, right? Remember seeing Kirk not too long ago? Yeah. Okay. Was that exciting?

He flew out to see you? Is this like payback or something? No. Oh, no. No. No, it's not payback or anything. It's Kirk. We talked to to him and he just told us the story about how you guys met online and you talked for like a month or so then he flew out to surprise you and that's when he found out you weren't quite the same person as you put in your profile

pictures um i'm just wondering now how did you feel when he showed up that day and saw you i was mortified yeah oh you know i didn't know he was coming yeah and he was there like in my face yeah it was i mean i would feel almost ambushed i mean because you you had been betraying you know somebody else and totally right i guess i want to ask like has your feelings changed since you saw him because he said you guys sat down for drinks afterwards and things seemed to go pretty well they yeah i mean my yeah i would say my feelings have changed a little bit so i mean he he okay he obviously had to process the whole physical part was different right than he expected and you can understand that that would be a pretty big shock i I was taken aback as well. Yeah. Do you mean like by his physical appearance? Totally.

Absolutely. Oh. Oh, wait. Kirk looked different than you thought he was going to look? I mean, in his picture, he didn't have glasses. And he's got glasses. Okay. That's a big change. but you can take a lot.

A lot of people, like I wear glasses sometimes and sometimes I don't. But we do make fun of her a lot. Yeah, I do prefer Brooke without the glasses. So I can understand that. No, we're kidding aside. Is that a joke? Like Clark Kented you or something? I mean, when he had his glasses on, he kind of looked older.

And like that character, there's a south park character i can't remember his name mr mackie yes the guy who's like okay oh that guy yeah he's older he wears glasses yes yes he wears glasses and he reminded me of that character it's a good picture to paint i was like projecting your own feelings like on him oh hey i am not blaming him but he didn't look like his picture either okay that makes me laugh sorry he said that you used a completely different picture on your profile like it wasn't even you at all yeah and we've been through that already and but you're asking me how i felt about him and i'm telling you he looked older maybe like eight pounds heavier that's so specific okay not even 10 so okay wait are you saying that you

like you aren't attracted to him? It's just different. Oh, wow. We had a big connection on the phone. Yeah. Yeah. Okay. Okay. And so glasses and eight pounds ruins that.

It's not what I think we were expecting when we called you at all. And look, Jillian, I know that Kirk already surprised you once, but he's actually going to be surprising you again right now because he's been quietly listening on the other line and he wants to talk to you. Hello. Oh, come on. Yeah.

What are you doing? What, what am I doing? I cannot believe you just said all that glasses and eight pounds heavier. And I mean, it's still me. It's still me in the picture. The picture that you had wasn't even you. But I, I was remorseful for that.

Oh, she can feel bad. She knows she did something wrong. Yeah. And I know that. And that's why we talked afterwards. Remember? And we, we spoke about that and you shared your feelings with me and I, we, I know we haven't spoken for a while. But I was hoping to keep talking to you. And now I'm kind of, like, confused. Well, I'm just being honest with you.

And I can't get that South Park character out of my head every time I speak to you. Are you wearing your glasses right now, Kirk? Maybe you should take them off. I'm about to put them on right now. Don't do that. I'm great with put them on right now. Don't do that. I can't believe this. Jillian, do you think that there's any way... I mean, you guys just had a

really bad first meeting. There's a lot of surprises, a lot of big, huge emotions. Large glasses that came out of nowhere. I mean, maybe you're just making this as an excuse just because it was just icky. Yeah.

Is this embarrassment on your part, Jillian? As I've said before, I am remorseful. Yeah. But that doesn't excuse what he did. Well, this is crazy because this is two people who just a couple weeks ago was saying that they loved each other. Yeah. And now they're on the phone and I can sense all this tension. And Brooke, I think you would agree.

We can fix this. Yeah. If Kirk would just apologize for not sending her a photo of himself wearing glasses. That was his bad. Kirk, can you own that? Can you say I'm sorry? Hey, look, I sent you guys an email so I can talk to her. And now I'm the one who's apologizing to her for wearing glasses?

I'm just saying, Jillian apologized to you. No, Jeff, will you stop? She is being sarcastic, Kirk. You don't need to apologize. I mean, I do think you could say something nice to Jillian if you still even want to go out with her again. You know what? That's the thing. Like, I wanted to go out with her again.

I wanted to continue to talk, but after this, I don't. And she wants to go out with you, too, as long as you lose the glasses and the wig. So with that being said, Jillian, we would love to send you guys out on a second date, and we will pay for that. I mean, I'm not happy about this. I'm just letting you know that's why we haven't been talking. Well, that's how most married couples are. They're not happy with each other most of the time.

I think that's a very, very good thing. But they still love each other. They do. I mean, I'm worried about bad habits. Bad habits. Oh, like catfishing. Like bad vision? No, I mean, I'm just saying, like, it could be a poor diet that leads to poor hygiene

and then maybe, you know, bad eyesight. Guys, you know what? Just stop because I don't even want to do this anymore. No. Dude, you don't mean that. No, I do. I do. This has gone totally left.

Oh, man. Oh, wait. So now you don't want to go out with me? What? Stop. What? Wait. You just said you would think about it.

I'm lost for words. I was going to actually pay for you to come see me, and now it feels like that would be a waste of time. Yeah. And money. But I didn't say that I didn't want to come see you. What? Well, you never said you wanted to either.

But didn't you read between the lines? Oh, my God. Just hang up. Hang up. We got to be done. Oh, no. Oh, no. Who knew that a catfish across country could turn out like this? This is the most romantic story that I think we've heard all year.

We don't do very good romance on this show. This is the best that we have to offer. I wanted to DTFIL, Jeffrey, and it's ruined. I think we all were DTFIL, but instead we're just SOL. Oh yeah. Got it. Brooke and Jeffrey in the morning. I think we all were DTFIL, but instead we're just SOL. Oh, yeah. Got it. Brooke and Jeffrey in the morning. Jon Stewart is back at The Daily Show,

and he's bringing his signature wit and insight straight to your ears with The Daily Show Ears Edition Podcast. Dive into Jon's unique take on the biggest topics in politics, entertainment, sports, and more. Joined by the sharp voices of the show's correspondents and contributors. And with extended interviews and exclusive weekly headline roundups, this podcast gives you content you won't find anywhere else. Ready to laugh and stay informed? Listen on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. minutes, we dive into one global business story that matters. You'll hear from Bloomberg journalists like Matt Levine. A lot of this meme stock stuff is, I think, embarrassing to the SEC. Follow the Big Take podcast on the iHeartRadio app, Apple Podcasts, or wherever you listen.

People, my people, what's up? This is Questlove. Man, I cannot believe we're already wrapping up another season of Questlove Supreme. Man, we've got some amazing guests lined up to close out the season. But, you know, I don't want any of you guys to miss all the incredible conversations we've had so far. I mean, we talked to A. Marie, Johnny Marr, E., Jonathan Schechter, Billy Porter, and so many more. Look, if you haven't heard these episodes yet, hey, now's your chance. You gotta check them out. Listen to Questlove Supreme on the iHeartRadio app,

Apple Podcasts, or wherever you get your podcasts.