Brooke and Jeffrey: Second Date Update - Second Date Update: Standup Funny Man

Episode Date: January 5, 2022

Every once in a while we have someone on the show that is so unique they're unforgettable... And today is one of those days. We are so excited for you to meet Harold!See omnystudio.com/listener for privacy information.

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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,

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Second Date Update. Over the years, we've had people with all sorts of interesting professions call in for a Second Date Update. Oh, yeah, for sure. And we've had a few former pro athletes, a movie stuntman. Oh, yeah. And one time, we got a junior-level auditor at an accounting firm. I mean, that was interesting to me.

Was it? Like big numbers? Well, mostly because my parents do all my taxes, so I don't know anything about that stuff. It's fascinating. But today's phone call is pretty special because we have someone on the line who says they have one of our jobs, and that's a professional stand-up comedian.

Just like Jose Bolaños. Who do I know? Well, there's a lot of us out there. I don't know if you know. Are you guys going to out-joke each other? Oh, my God, it's Kevin Hart? No. His name is Harold, so please welcome to the stage, Harold.

Yeah, Harold. How's it going, everybody? Hey, see how natural he is? Is that a fake accent? Is that part of your shtick, Harold? Fake. Ain't nothing fake about me, dear, but my fingernails I got on. Okay.

Okay. Okay. Oh, all right. Can we laugh? No, I like this guy. All right. Harold. This guy's going to take my job.

Okay. Thanks for being with us, man. So before we get into your date, first tell us about the girl that you met. What's her name? Oh, her name is Ashley. Ashley, okay. How'd you meet her? I met her through this date nap, but, you know, that's a whole other chickaboodle.

Yeah. You never know how boring you are until you start filling out that darn thing, I tell you. Seriously. I feel like this is a setup. The whole thing. For his next joke. But I agree with you. I'm telling you, though.

But you know what? As I was filling it out, I kid you not, I realized, hey, wait a minute. There's millions. I'm talking billions of people out here who's not dating me. What the heck is their problem? Yeah. I feel you, man. I feel that way all the time.

I'm like, how come I only have 2,000 people dating me? Where are my millions? So did she hit you up? Is she the one that reached out to you on the profile? Oh, yeah. I feel that. I mean, you know, I just want to meet somebody nice and get into a relationship. Yeah, that'd be great.

A serious relationship to me is like freaking a marathon. It's all stupid. Huh? I thought you wanted to be in a relationship. Well, I'm just saying, I wouldn't mind being in one, but for the most part, you gotta go through all this foolishness. Can we just focus maybe a little bit?

I'm really enjoying your perspective on life, Harold, but can we get to your date with Ashley? Yeah, but I just figured you want to know how I came about doing all of this. We get the idea. You met her online.

What exactly did you do with her? We went out to go eat to this restaurant. Harold, how was the conversation between you and Ashley? Because if it's like this one, I may know why she's not calling you back.

Well, it was a 10-hour date. I tell you, I was going to make her smile and laugh throughout this whole evening. Are you saying that you ran a comedy bit on her? Yeah. Well, not really a comedy bit. I just told her a few things that I believed in. For instance, I told her, I said, you know what, Ashley? She said, what, Harold? been like for instance i told her i said you know what ashley she said what harold i said

you know you're like a jellyfish jellyfish and i said your body's rudimentally and i'm just i'm scared to get near it what that was a good one what they call a Harold-ism. Okay. So you're scared to get closer. We don't body. This is where, did she laugh? She chuckled after all get out. And then I followed it up with, I said, you know what, Ashley?

She said, oh, what, Harold? I said, you know, relationships are the darnest thing. They're 90% are trying to figure out where we're gonna go eat at okay yeah so i'm good on the heraldism over here i really i do appreciate though you reenacting ashley answering your questions because i really feel like i'm there can we get back just to the date again how do you think your chemistry was you feel a connection there i did i mean i was getting ready to walk her up to her door after we concluded a nice little dinner and

walk around the lake but i was telling her what i thought about doing i'm sort of glad i didn't she was like well what's that i told her i said i was going to wear a parachute tonight to our date. A parachute? Hold on, just play along. Why are you wearing a parachute? Can you just hear me out? Oh, I'm trying. I don't know why I was going to wear it, but I figured it was going to start up a conversation.

Wait a minute. You didn't have a punchline? There's no joke. Harold, Harold, you asked her, wait, hold on. Where's the improv? You told her you were going to wear a parachute and when she asked why, you didn't have an answer?

Right. I showed it to her in my trunk. I said, if I got here and I didn't feel my mojo and I didn't feel like myself, I was going to strap on this here parachute and walk in this here restaurant. Wait, there was actually a parachute there? That's what he said.

He said he had an actual parachute in the back of his truck. Follow along, bro. I thought it was a figurative parachute. You never know when a good parachute joke is going to come up. No, but think about it. Somebody was going to have to ask me. She was going to have to say, now, Harold, why are you wearing this

here parachute? But she didn't say that. Well, I didn't wear it, but I'm telling you, I felt good about myself and I had my mojo. Well, I feel like I've gotten a pretty good idea. It sounds like you guys had a lot of chemistry. Is that what you got out of this? Jeffrey, that's what you got out of it chemistry maybe let's fast forward to the end of

the day how did the night end with you and ashley i thought he was walking her to the door well i'd like to get to the very finish what's the last thing that happened was there a kiss was there a hug i'll tell you what now and i'll be very forthright with you okay for the first time when i went there i went went in for that little kiss, and I was ready to embrace this. You know, like how they show on television, just a long, drawn-out thing. Yeah, romantic. While you were wearing a pair of shoes.

No, Brooke, don't sing it out. My God, it's nothing to happen. I mean, heck. But I tell you, I mean, I said, thank you, ma'am. And I walked about four feet and I turned around and I said, you know, if you want, you can call me CB. CB. CB. I say, yes, it stands for coffee bean. And then she says coffee bean. And I walked another two steps to my car and I turned around and I did a thrust. I said, yes, because I grind so fine.

I told her, just like Maxwell House, I'm good to the last drop. Yeah. Well, that sounds like a pretty great time. to the last drop. Yeah. Oh, boy. Oh, wow. No drops. Well. Oh, God. Harold, that sounds like a pretty great time. I am. Wow. For one of you.

Jeffrey. In your mind when you look back on the date. Yeah. Don't ask. I don't think we should ask more questions. Listen, stop. You don't think I should ask if there's any moment that could have gone wrong? No, no.

Please. We'll be back. We'll be back. We'll be back. Okay, let's play a song. Thank you. And we'll come back, and then we'll try and get you your second date update. All right, CB? We'll try.

Good, because I got a whole plethora of a short list to tell you guys about. All right, all right. We're going to take a short intermission. We'll be back with more of Eric. Second Date Update. If you're just joining us for the Second Date Update, we've been talking with one of our listeners named Harold about his first date with a woman named Ashley. Now, Harold is a stand-up comedian, and he went into a lot

of detail about their night. But here are the main points that I took away okay they went to a restaurant he drove her home yes he pulled a parachute out from the trunk of his car and he even got a short peck at her doorstep even though he was kind of hoping for a longer sloppier kiss you were missing the very end he said swap and spit what's the very end he wanted to grind on the cb the coffee bean oh well he has a nickname he likes to go by cb which is short for coffee bean because he grinds so fine yeah yeah that i feel like is a really important last ending shot of his day one thing was abundantly clear to me though and that's that he had a really nice time with ashley

and he's bummed that she's not calling him back. That is true. Now, Harold, about ready to make your phone call here. How you feeling? I'm just so appreciative of you guys doing this here for me. I mean, I went jogging the other day, and man, I saw this couple holding hands, and I just started thinking about this little filly, and I'm like, oh, man, this makes me hopeful that one day I can find the right person that will hate that couple just as bad as me

i'm just hoping it's gonna be ashley that's what i was thinking you can roast people together i hope that for you too harold harold we didn't hear i mean have you reached out to ashley and she hasn't called you back i said her a couple of texts and I even called, but I got nothing. Okay. So you reached out to her a lot is what it sounds like. Okay. Not answering your texts. Well, maybe we'll have better luck here because I'm ready to dial her number and we're going to try and get you your second date update.

You ready to do this, ma'am? Yeah, let's go for it. Okay. Remember, I feel like I have to say this. Wait until it's your turn to talk. Jeffrey will handle it from the beginning. I'll call you in when I think you should talk to her, okay? I tell you guys, that might be a little tough to do because, hell, I've got a lot of heraldisms I need to get rid of.

Okay. We're trying to get you another date, Harold. So just dampen the heraldisms just for a couple minutes. Less is more. Less is more. Let me try and get some a little bit, okay? Less is more. Let me try and get some answers from her, all right? All right. All righty.

Okay, here we go. I'm going to dial her number right now. Hello? Hi, I'm looking for Ashley. Who is this? Hi, Ashley. My name's Jeff from the radio show Brooke and Jeffrey in the Morning. Who did you say this was going to be? I'm sorry.

It's okay. We're a morning radio show. Okay. We're called Brooke and Jeffrey in the Morning. And we're reaching out to you today because we heard that you love comedy. I'm sorry. What is this about, though? I'm confused. Well, we're a comedy radio show and we have a friend of our show who also does comedy.

That's not, that's your friend. No, no, no, no, no, no, no, no. She knows. Is this about that guy Harold? Oh, girl. It might be. Oh, no, I'm okay. Thank you.

No, no, hold on, hold on. I'm sorry. I am fascinated to hear your side of the night. Yeah. He told us about your date. And what we're doing here, it's called a second date update. We're trying to help Harold understand what went wrong during your first date. Because believe it or not, he doesn't know.

Yeah. Wow. That's amazing that he doesn't. Yeah. Yeah. So we need your help. Yeah, because we all understand that Harold is a one-of-a-kind type of character. Yeah, he sure is.

You know, so is there something about him or about the date that was a problem for you? Well, you know, to be honest, some parts of it was fun. Because he's a comedian and so his jokes were even a little bit fun. Okay. But some of them I didn't even have a punchline, you know? Like, I just looked at him. Yeah. And then, you know, he just talks a lot.

Yeah. I'm not sure what you mean by that. Yeah, of course you do. I mean, did he ever take a second to, like, ask you questions? No, that's the thing. And that's the thing that made me kind of go like yeah this is not gonna work because for me the number one thing i need is a phenomenal list well i mean sometimes people talk a lot when they're really nervous because they're out with someone that they like yeah but that's okay 70 percent of the time okay i get it get it. Get a glass of water, you know? Like, take a second. I understand how you're feeling,

that maybe you don't know if there's a bond there, but I don't know if Harold would necessarily agree with you on everything. You know, he probably would make a joke about it to me. Or try to. I mean, there may not be a punchline, but he'd try. He sounds like a sweetheart in his own way. Does he? How long can you last with that?

A day? A day? A week? No, I wouldn't even give it five minutes. See? Well, maybe just give it five more minutes because I need to let you know that Harold is on the other line listening and he does want to talk to you right now. Oh my God. Are you serious, man?

He has not spoken one word this entire time. Harold, are you there? It's been hard, I must say. But I just want to clarify something real quick. Now, Ashley, I hope you know when I talked about putting one arm around you, getting my other arm, putting it around you, and squeezing you tight and just tackling you. I'll be honest. I was talking about relationships.

Then my mind went to football, and I just went right there's a distraction that doesn't make any sense well that's what that's what happens when you're in love like things don't make sense anymore things start running together can i can i ask ashley was there any jokes that made you laugh of harold's and you said one about a pop-up i'm trying forget. I don't even want to think about that to be honest. I don't think we heard that one. I can't discuss that one on the radio. That's a live joke. It's a live one? Okay.

But I tell you, I mean, I would love to spend some more time with you so we can go over a few. That was funny. No, no, no, no. Harold, you're missing the point, dude. Are you not listening to her? I'm going to make the next thing all about her. That's what I'm trying to tell you now. How, Harold, how are you going to make it all about her? I'm going to just sit back, relax, put my feet up, have my guitar,

and just sit alone while she's talking away. Wait, guitar? That's nice. Give her a little background track for her to talk over. I wouldn't be able to hear the answers if you play the guitar harold yeah i mean because you put me on the spot that i talk so much i'm not saying a thing i'm just gonna listen to you no that's not what she wants that's exactly what she wants she wants a man who is a very very deep listener you're not listening if you're playing guitar. You can do both.

You can play guitar and listen. Harold sounds like a very multi-talented person. You darn too. Tell him, Ashley. Tell him exactly what you want right now. Like, just listen to what I say. Ask me questions about me.

Don't make me feel like you're testing out your jokes. Okay. Do you want to give it a try right now, Harold? Why don't you ask her a question about her that has nothing to do with you? right let's practice do you like whipped cream ashley i yes i do okay now do you like the little whips what whips like a leather whip now i'm just trying to find out

about her guys yeah okay he's trying to find out about what types of foods you like ask her real questions like about what she likes what motivates her in life what her so picky it's like oh now there questions? Okay, okay, let me ask you this most important question of them all. All right. Do you like Cinemax after Dark or HBO Plus?

What? I like HBO Plus. Okay, okay, now we getting some way. We're not going anywhere, Heather. Are we getting to the end? That's what we're getting some way. We're not. We're not going anywhere, Heather. Are we getting to the end? That's what we need to get to.

Yeah. I'm going to be honest with you. I'm feeling some synergy here, guys. I am too, Harold. And you know what? That's why I would love to ask Ashley, would you like to go out on one more date with Harold? We will pay for it.

Dinner's going to be free, and so are the jokes. Yeah. Free comedy. The dinner sounds Dinner's going to be free, and so are the jokes. Yeah. Free comedy. The dinner sounds great, but to be honest, I don't think I can stand the headache of not being listened to. That's really a big thing for me. That's not shocking. You want me to leave the guitar home?

Oh, my goodness. Or I can put it in the trunk in case you change your mind on the date. With the parachute. With the parachute, yeah. With the parachute and the guitar together. Will you bring your ears today most certainly will i have no problem with that i just need to spend some more time with you it's really sweet actually dude don't i mean you're jokes were funny some of them some of them i'm gonna be honest with you you know if you just eat a peanut butter sandwich, it's all good.

But there is nothing like peanut butter, jelly, and banana. And Ashley, you're that banana. Oh, boy. And you're the peanut butter and the jelly? Where's the bread? I don't think more romantic words have ever been said. Wait, are you actually changing your mind on this, Ashley? Are you actually turning?

I don't know. I mean, he is kind of cute. Oh, my God. Oh, my God. This is working. I mean, boys and girls, do you hear that? She said it. There's some synergy up in this here air.

Oh, I feel the synergy, too. Okay. All right. Ashley, we're sending you out one more time. Even if you change your mind, you're going out on one more date with Okay. Oh, my God. Ashley, we're sending you out one more time. Even if you change your mind, you're going out on one more date with Harold. Okay. Oh, my God. You have to update us on this because I need to know how the second night went.

Harold, are you feeling happy right now? I'm a little speechless. I can't even tell. Oh, that's exact. Keep with that. Stick with that. Go with that feeling. Brooke and Jeffrey in the morning.

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plus special financing for a limited time. Only at Sleep Number stores or sleepnumber.com slash podcast one. Sleep Number, the official sleep and wellness partner of the National Football League. Subject to credit approval, minimum monthly payments required. See sleepnumber.com for details. Catch Jon Stewart back in action on The Daily Show and in your ears with The Daily Show Ears Edition podcast. From his hilarious satirical takes on today's politics and entertainment to the unique voices

of correspondents and contributors, it's your perfect companion to stay on top of what's happening now. Plus, you'll get special content just for podcast listeners, like in-depth interviews and a roundup of the week's top headlines. Listen on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. to give you the context you need to make sense of it all. Every day in just 15 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.