The Truth About Dating in Your 20s with Luke Lenny

Speaker 1 (00:00.206)
Welcome to Guy's Set, the guy's guide to what you should be talking about. I'm Josh, I'm 23 years old, and I'm here to find all the tips, advice, and recommendations for guys in their 20s. Let's get into it.

Speaker 1 (00:18.104)
Hi guys, welcome back to guys said this is part two of my interview with my friend Luke Lenny. So if you haven't heard part one yet, go back and then come back here or if you don't want to do that, that's fine too. This part is great on its own as well, but I recommend listening in order. I split them into part two and part one because it was a really long episode we recorded for so long and it was really great. So I didn't want to cut it. I believe that part two of this interview is one of those episodes that really captures the mission of this podcast. And that is to talk about what should be talked about for guys in their twenties.

And we just have a really genuine and honest conversation about first dates, how to wrap up a first date and what to say at the end if it's going well and if it's not going well. When to text them after that first date, his recent worst first dates, one of his recent best first dates, advice for first dates in general, not putting pressure on things like a date or two. We also talk about finding confidence, which I really loved and the balance of

confidence and cockiness, I think people can get stuck on and it's a really important like differentiator. We talk about breakups, fashion, skincare, shaving. Luke also just bought his own apartment and moved out from his two roommates and is now living on his own. So he takes us through the steps that it took to buy his own apartment and how he's feeling about living on his own for the first time in his life, which is really cool. And this is just a really genuine good episode filled with very honest banter about

dating and life as guys in our early twenties. And I really respect Luke for being as honest as he was. You'll see in this episode that we actually get into the topics that can be super uncomfortable for guys to talk about. at one point, like you'll hear me mumbling a bit and trying to kind of stumbling over my questions as I did just there. and that just showed that like I was a little uncomfortable asking some of these questions and having this conversation. And to me, that just said that like, I don't have these conversations that often and a lot of guys don't and we should have them more often.

So again, just mad respect to Luke for being so vulnerable and being comfortable putting his experiences and what's going on in his life out there for the world to hear and just show that guys can have these conversations. without further ado, please enjoy part two of my episode with my friend Luke.

Speaker 2 (02:38.37)
I like I can tell pretty quickly in a hinge conversation if we're gonna get along.

Speaker 2 (02:44.455)
to like pinpoint because you know what I say that but I've also had really good text conversations with people and then I meet them in person and it's a complete

total dud. Yeah, let's talk about that. Thank you for thank you for transitioning. Yeah, next question. Okay, I want to talk about first dates. and let's, I want to let's start with a good one. Because let's start with start with the good. So good one. What let's let's hear about like a recent good first date that you've been on. And that like you've planned.

First dates, okay?

Speaker 2 (03:12.526)
Okay, I went on a first date. We walked around the East Village. We got a 7th Street burger. Yeah, shout out to 7th Street Burger if you want to sponsor. We got a Rowdy Rooster sandwich, which you're now familiar with. Shout out EatsCon. A little food tour. We got one sandwich from each and then we went to Ray's Candy Shop. Got some fried Oreos.

Shut up.

Speaker 1 (03:34.84)
So it's like a little food torso.

Speaker 1 (03:41.422)
Dream first date.

We were gonna go I can I'm three

hahahaha

We were gonna sit down in Tompkins Square Park and eat. I brought a little towel I bought a bottle of wine. I had a backpack on I look like a schoolboy

Yeah. But it's like a really nice plan. you had an idea.

Speaker 2 (04:03.014)
Yeah, I was cuz I can't remember she lives in Little Italy I don't think she tried a lot at East Village place. I was like, I'm gonna take you a couple of my highlights and Yeah, we're gonna we're gonna sit in Tompkins Square Park, but it was getting kind of dark I have to burp hold on. Sorry

Cool. Sounds like great first date.

Speaker 1 (04:19.959)
Okay.

Disgusting together you're on a podcast

and It was getting kind of dark out and that park is a little bit sketchy your evening, so we actually went to Such a shame. I don't know the name of this brewery. It's on 8th Street and You can sit down like outside they got a nice like outdoor area heated if it's cold out You can sit down and bring your own food and just have to buy Yeah, we just sat down there ate everything tried everything

Yeah, yeah, absolutely.

Speaker 1 (04:42.849)
Okay.

Speaker 1 (04:51.64)
Sounds great.

Speaker 1 (04:58.478)
Sounds like a really good first date, but I will say like it sounds like a very unique first date because Like a lot of first dates I think are like Go to go get like a couple of drinks and like let's know them or like yeah Is that is that your usual like thinking of something that is fun or something more? No That's a really good highlight first date, which I did ask yeah, I want to hear about like other like Yeah, cuz I want to get like

That's not that was more unique

Speaker 2 (05:22.03)
standard classic

The point is like here to give advice to people who have no idea what to do for a first date.

I mean, think that drinks, like drinks is safe. I think that like, especially if you're nervous, like have a drink or two, like you feel a little bit, you know, a little bit better, but.

What do you recommend like a wine bar like a speak like a cop?

I do a wine bar that I really like it's called BB wine bar 4th Street Yeah They do $30 bottles from 5 to 8 p.m. Every weekday Absolutely fantastic if you're somebody that's gonna go on a lot of first dates like you want to just meet some people It's a good spot. Yeah, find a spot with a deal because you will go broke

Speaker 1 (05:53.144)
Great deal.

Speaker 1 (05:59.416)
find a spot like that.

Speaker 1 (06:03.534)
100 % no, it's something in the last step then like the guys that took an episode somebody asked about budgeting Yeah, and I was like going on first dates like it's really hard to budget. It's so expensive

I think the second first date I went on in New York, I spent $140 on espresso martini.

Holy shit. Yeah, that sucked. Well, there you go. But like, yeah, that's your good literal broke like you were. You can't hold that up. So that's a that's a good tip. Like finding a deal. Yeah.

We had like four espresso martinis each. I didn't go to sleep. Five hours after.

Speaker 2 (06:32.664)
Don't want to do that.

Speaker 2 (06:39.294)
Agreed. Other than that, I mean, I will say the reason that that date was a little more special is I hadn't been on any dates in a while because I've been traveling so much. Like when I was traveling for work, it was Monday through Thursday, which is normally when I would go on dates. I was traveling, obviously, and then I come back Thursday night exhausted, go to sleep. Friday, Saturday, just want to see my friends who I haven't seen all week and then Sunday pack for that. There's no there's no time to do that. So

Great.

Speaker 1 (07:03.35)
No time.

Speaker 1 (07:07.182)
So let's say that date went well. Did it go well? The food tour one? If a date is going well, what do you do? At the end, let's say it's like a two hour date. What do you do? How do

Pretty

Speaker 2 (07:22.208)
Is this like like a do you lean for the kiss kind of question? I personally say no. If a date goes really well.

Yeah, 100%. Okay. Okay. Which is by the way, something I never, we have never talked about, I don't think. Really? No, I don't think we've ever talked about this.

Really? Okay, well that's my official stance on the matter.

is no, do not lean in for first kiss after the first date.

Because if it really went well, well first of all, could have gone really well in your head, might not have gone really well in her head. You don't know. So I think that the best way go about it is just like, I had a really great time, I would like to do something again sometime, I'll let you know. I think that's a great way to wrap up first date. Give a hug. Because if it really did go well, you'll see her again.

Speaker 1 (07:46.638)
Okay.

Speaker 1 (08:05.262)
100%. So which is by the way, like a very good answer to that question.

as simple as that.

Speaker 2 (08:11.278)
Like take the pressure off you and her. Don't, don't. Try it. Yeah. Don't, don't try and romanticize. Don't do that.

Don't put it on a-

What it doesn't need to be. Yeah. Will you attempt to like walk her to like a cab? okay.

No, walk her to the subway. Wear whatever subway she's taking. I think that that's just respectful to ns. Especially if it's n. Don't send off your first date or-

Yeah, star. Yeah, 100%. Yeah. I'm not saying that I do. I'm just Josh. Okay, let's say it goes badly. Let's talk about like a what's your worst first date or a recent bad first date.

Speaker 2 (08:38.446)
doing that.

Yes.

Speaker 2 (08:48.494)
I think the worst first date I had I'm not gonna get too into specifics of it. But okay, the general gist is it was somebody who Had recently gotten out of a relationship and she was not ready to date yet, but decided to go on a date

it did you know that she had gotten a relationship recently mid-date yeah that's really bad

No. But I found out. Yes.

was not fun. We had a bottle of wine at my wine bar and the waiter came over and asked if we wanted another to which I was going to respond no we're okay thank you but like a date experience you had right they decided to say yes we'll take another bottle yeah so

Okay, bye Widenberg.

Speaker 1 (09:33.492)
my god. Without consulting you. Which is something, it's such a crazy move. It doesn't happen all time. A hundred percent. By the way, she knew that you were paying.

Especially when I'm paying.

Speaker 2 (09:47.438)
Yeah, from how everybody knows.

Right, we don't have to like act like it doesn't know that when we came back at my date and was like one other drink and she was like Absolutely. Are you fucking kidding? Yeah, it's like we're not you're simply spewing at me. Like this is not a like whatever the date but go ahead so she

was fine, it was fine before that. So we're a bottle of wine in. alcohol, depressant. So if you're sad and you drink, you're just gonna get more sad. That's how works.

100 make it happy for like a minute. Yeah, 30 minutes might maybe leading. It's a fleeting feeling happy. Yeah

Get out.

Speaker 2 (10:23.546)
But yeah, we ordered another bottle of wine and at this point I'm like, oh god, I don't know what I'm getting into here But they're like no real red flags yet. And then I don't remember how her ex came up but he came up and Whatever I did the conversation went back to him for the rest of the night. Oh And yeah, this is like getting teary-eyed It was not good. It was very bad

I'm uncomfortable hearing that.

I cannot imagine what the rest of the wine bar was thinking at us at this table. Like not full-on balling, but like yeah, like it was not good. Yeah, and at this point I'm like just slamming cups of wine trying to like finish this bottle very quickly. And I walked her home.

She was crying.

But she was crying.

Speaker 1 (11:11.79)
How did you leave a bad date? or how do you end it? Because in this one, like you couldn't end it. Okay. And then were you like, all right, let's go or like, all right, like we've had.

I did it by finishing the bottle of wine. Yeah, I was...

The waiter came back, was like, can we get the check? And at this point, I think she kind of realized like, wait, I probably shouldn't be on this date, Very specific.

got it yeah but it's maybe another one that's like not as insane of like it's it's going okay but you know it's nothing nothing's gonna come yeah like how do you end it there

to check.

Speaker 2 (11:52.576)
in that you owe them the standard time of a date. Yeah, if you misjudge someone's vibe over text, which is hard. Yes, exactly. But I've been on a date where, and this was tough because I think she was just nervous. She was the year below us. So I wouldn't be surprised if it was one of her first dates in the city. This was over the summer.

Totally.

Speaker 1 (12:03.434)
It's hard. You have to meet somebody to get to know-

Speaker 2 (12:20.142)
She just like kept talking over me like asking me a question I'd start to answer and then we just like start talking Like I just I could not talk and it felt like nervous to me Right to the point where I was like, I kind of just gave up like I was just drinking my wine letting her talk. Yeah, and But again, like if you ask somebody on a first date like I think it's just you kind of owe them that time So if it's not going well, like suck it up

Again?

Speaker 1 (12:47.886)
And when you say time, what, like an hour and a half, an hour? An hour and a half. Yeah. Yeah, no, I agree. Like you do have to suck it up and just like be like. Like.

Between an

Speaker 2 (12:55.208)
Don't be an asshole and just leave or something. No, don't make something up and like I just it's not yeah, I don't know

Okay, do you think me saying that like, ugh, I have to get up early tomorrow is making something up?

No, if it's been that long. Yeah. I think if you've done the hour, hour and a half long of first date, then I think you can, I mean, yeah, then from there you can make up any excuse to go home.

And then, then like, I want to run through this like specifically, because I've had two now that have just been like, I don't know what to do at the end. Yeah. Take a sip of twee. Yeah. After the date, like, let's say I've gotten the check, like, what do you do now? You're like, all right, like, really great to meet you. Nice knowing you. Like, what, what are your words at that point?

I think I'll say something along it's like you ready like to head out right and then I'll ask Like what subway you're taking like I can walk you back to the station

Speaker 1 (13:43.404)
Okay, and then when you get them there, like, nice knowing you or, really nice to meet you.

yeah, I'll give him a hug. Great meeting you. I go back and forth on this, like saying like, let's do something again soon because especially if you know you're not going to do something, like I think it's fine to just say like, it's great meeting you. Like, yeah, get home safe or like, have a great rest of your night. Yeah. Or if anything happened on the date, like if they told you about something at work tomorrow, like that's something good luck on this. Yeah. I think that's a good way to end dates. Okay.

Yeah

Speaker 1 (13:57.563)
Right.

Speaker 1 (14:04.866)
Get home.

Speaker 1 (14:13.902)
Yeah, that's a good.

But I do think if it went well, it's important to say like, let's do something again soon. Yeah. Switch, honestly, I'm kind of settling that debate in my head. I think you only say that if you actually, like don't say that. Just be nice. Great. Because it's easy to say that even if you know. Because you want to, because you don't want to be mean. Like you want to make them. Like we're not trying to make people feel bad, but also like don't put some, don't be like, I want to see you soon if you're not. Just suck it up. Yeah.

It's so.

Speaker 1 (14:34.306)
We're all good people here.

Speaker 1 (14:41.358)
Not gonna see the video, it is kinda fucked. When do you text, this is the one you wanna see again, version A. When do you text that girl again and be like, hey, when are you free or hey, would you wanna do something Wednesday night, whatever you're say.

This is something I think I got better at. Yeah, I actually think you should not, unless they text you after the date, I think you should not text them. Yeah. Maybe check in, no, no, no, I mean like that night. Yeah, maybe check in to make sure they got home safe or like even like when you're letting them go, say, hey, just let me know when you get home. Because then you'll hear from them, you'll be like.

with time.

Speaker 1 (15:13.814)
Okay, okay, so yeah

Speaker 2 (15:24.832)
Again, you can reiterate it over text, like, I had so much fun, let's do something again soon. But give it time. You just spent an hour and a half.

You give it to like tomorrow morning, tomorrow afternoon.

No, think yeah, I think you could wait till like the day after work like cool honestly, you could probably wait a little bit longer in fact I Would argue it's like not the worst thing in the world to wait till you want to see them again Like maybe the next week. Okay. Yeah, and that's something that I feel like I've done more recently I think that I've realized more and more that like texting doesn't Really mean anything. Yeah, like and I think it means you kind of have to gauge it out by person

Like I think texting frequency means different things to different people.

Like you don't want someone to think you're ghosting them.

Speaker 2 (16:09.11)
Exactly, but you also don't want be like bombarding them with texts if you just met them So I think you kind of feel out kind of where they're at

Right, I feel like there's never like a, like this is a rule, like text them like.

Text them 48 hours and 30 minutes after. No. I think it definitely varies by person.

Not

Okay, so get their vibe and then either text them like, I want to say I want to give like not like a blanket like maybe like the next afternoon next couple days within that time period time.

Speaker 2 (16:37.47)
I that's fair. Okay. Yeah. And I think maybe circle back on something they talked about on the date, like show that you were listening. Okay. And then maybe bring up like, are you free next week for something? Right. Yeah. Okay.

Okay, so let's say this date is going well. We've gone to like maybe one or two dates. How do you like gauge when you should like sleep with this person now? And it's not there's again not like a blanket statement, not like there's no rule.

I don't know. think it's really, like it just kind of depends. It's like such a lame answer, but like, yeah, sorry. I think that, I kind of think it goes the same. It goes in the same like way of thinking that I said with like kissing somebody after the first date. Like if a girl wants to sleep with you, like she's going to let you know. I don't know. I think that like,

I've again, this is something I've realized more now is just like don't force anything. course. Like I think that like a good way to gauge it is just like if you're going out on Friday and like she's asking what you're doing and you can ask what she's doing. Like, are you doing anything?

She's meeting that text back.

Speaker 2 (17:58.616)
Yeah, yeah, like I think it's really just kind of feel it out from there, but Yeah, there's like no real Hard wait, no. No. Yeah, you kind of that's one you kind of just have to feel out

I think, but like when you say feel out, mean like if she's meeting back your texts, like if she's responding back and it's going well and it seems like it's going in that direction.

I I think that for the most part, and this isn't 100 % a rule, but like if it's a Friday night and you're going out to bar with your friends and she asks you like, oh, where are you going? Or like you ask her where she's going and she's like, oh, like, do you want to meet up? Like, I think that that's like a sign. It's not a guarantee, you're drinking and like she wants to hang out with you still. Like, I don't know. I think that again, it goes back to the same things like

That's a good-

Indicators wrong word.

Speaker 2 (18:47.832)
meeting girls at a bar too. like, don't tailor your night around it. Totally. Like go do your thing. Go have fun with your friends. It'll happen. Yeah. If it's gonna happen, you know, I think that's kind of the best way to go about it.

Something comes up.

Speaker 1 (19:02.392)
No, that's a good piece of advice and it gets a great tip and like it's an important conversation for like, I think guys to have. Cause feel like, I feel like weed as our like friends, like don't really talk about like that topic. Do we? What are you? Or like any of this type of thing, like.

How do you know? Yeah, I think it yeah, it can only help right like there's an especially like if you're not sure

Totally. think you can always ask a friend for what they think or how they can read on that situation. Cool. for answering. Anything else you want to add in there about dating, dating advice?

data.

I have one thing that I think is really important. First dates. Because I think first dates, like that's like the hardest thing. It's like breaking through that barrier.

Speaker 1 (19:50.594)
by the by far farthest part. That wasn't English.

Yeah. No, not really. I'll pretend like I understood it though. Yes, it is. I think that the most, well, two most important things. One, be confident in just who you are. Like I think that the more confident you are in yourself, the better you'll be at dating in general. But I think that that's something that I've realized is

You know what I meant. I probably the hardest part is what I meant.

Speaker 2 (20:23.906)
Like girls can respect that. Like if they see somebody who's maybe, and this goes into, I think we're planning on talking about like dressing and how you dress. yeah, okay, cool. If you're confident in how you're coming across or like yourself, like I think that that's kind of how you break through that initial barrier of like being intimidated, whether it's a first date or whatever it is. So be confident. Yeah, which is like a heart. That's the easier said than done, obviously.

You're

Speaker 1 (20:50.566)
Don't forget your second tip, have a question on that. How do you balance cocky and confident?

Okay.

Speaker 2 (20:56.109)
Hmm.

I think I sometimes am not confident enough.

Think I have a good way. Okay. Okay. I think that I will make a cocky comment But then follow it with like kind of like a laugh like okay Like be a little bit too much and then acknowledge that that was a little bit too much, right? Right, right. That's a good Yes, like I think that's a good way to come across as confident because you might be saying something you believe but say it in a way that's like a little bit arrogant but like but like

Yeah.

Speaker 2 (21:27.934)
obviously a little bit arrogant and then like laugh about it.

Right, so if you're saying it in like a jokey manner, it's not cocky. Yeah. Totally.

Yeah, I mean it might even be, I think what makes it not cocky is like the follow up after of like, oh that was cool. Yeah. Okay. No, like an example. I? Maybe, okay. Let me give you an example. Let me give you an example.

That was cocky. Missing it? I feel like I'm missing it.

Your eyes are saying, your eyes are like, no, no, that's not what saying. You're like, actually, that's not exactly what saying at all. Yeah.

Speaker 2 (21:52.25)
I'm trying to think of a good example. Especially, think especially with compliments. Okay. Like if somebody compliments you.

Are you saying you're giving the comment? No, no.

Somebody's complimenting you on it like someone says like you have like great eyes Okay, like I feel like am I just you were dangling. Okay. Sorry. It's all the tweet. Yeah, Like yeah, I know and then like kind of like laugh. Okay, know what I Like, okay, I'm just messing with you like thank you and then say thank you obviously cuz I just gave you a compliment that Cuz you're you're like you're acknowledging like yeah, like I kind of think I have nice eyes too in like a cocky way, but then you're

That's a good one.

Speaker 2 (22:31.746)
you're, no, I'm not actually like that. I don't actually mean that like, my God, I'm so cocky in my eyes. But like, I kind of agree with you. You know what I mean? I think that's super, like especially with compliments, I think that's a good way. To like be a little, like to come off as a little more comp.

actually mean that.

Speaker 1 (22:47.778)
How did you build up to the confidence you have now?

I don't know. I actually don't know. I think so.

You are a very confident person. Yeah. think you're very confident in yourself and like you'll, I think that shows off on like what you wear. Like right now, if you're watching YouTube, you look very nice, but like you'll wear something like very random and like not give a fuck what anybody thinks about. Yeah. Which is something that like most people won't do.

Yeah, it's funny. actually, I feel like I went through a crisis of confidence last year. After college. Yeah, it was like early last year. I think part of it too is like post-grad, just like kind of figuring out new city. But I feel like I kind of lost the like persona I had in college because we weren't in college anymore. I like, wait, like what am I?

after college.

Speaker 1 (23:34.392)
Who am I?

Yeah, like I whatever image I for better or for worse, whatever image I had in college, like I had some kind of image, and now I'm in a city with bunch of random people around, I'm like, I don't really know anymore. I like I kinda had to build that back up.

What do think your image was in

Yeah, I don't know.

I think by the end it was just kind of like, it's like kind of all over the place, like kind of a mess. But like in kind of an endearing way. You got a little bit of charm.

Speaker 1 (24:08.789)
Act

A little witty? Yeah.

think that was kind of my image. Okay. Yeah. Not really, no. Okay. We're doing a little introspection here. I'm gonna have another sip of tea.

Have you ever thought about that?

Speaker 1 (24:22.088)
have a chug, have a chug. No, but I think it's important to get into that because like, when when what you saying like, be confident on a first date is like me saying at a bar. Yeah, because it's much easier. And that's why I wanted to dive into it.

Just go talk to her. much easier said.

No, you're so right. And I'm trying to like, there's no moment where I was like, wait, I'm confident. You know what mean? I think a lot of it is like, well, one, gym routine. think just being confident in your like physical appearance, feeling really healthy, I think is important for confidence. That's a really good one.

One of the reasons I go to the gym, like to feel.

Mentally, it's so important. 100%. I think it's so, so important. Even if it's not lifting, even if it's just going for a run, getting in a routine of like, that is, and there's, again, I'm quoting science that I don't know, I know we did this earlier in the pod, but that's real thing. Yeah. Feeling healthy and getting exercise consistently. Totally. Yeah.

Speaker 1 (25:19.406)
Okay, so that's one. Yeah, that's one. You sounded like you were like on like a and then you're like, okay, next thing.

Um, yeah, this is again, zeroing it and this is on realizing I'm confident.

Speaker 2 (25:35.63)
I think having things go well a couple times and even getting humbled if things don't go well. Even if it's a first date or whatever it is. Or even meeting new people, even if it's not in a romantic way. I think meeting strangers and feeling... Because when you're confident and you meet somebody, I feel like you can just lean into conversation. Totally. I've been in situations where I meet people and I feel more reserved after.

Uh-huh. And so I think like having like success, I'm gonna say successful, but like experiences where you're like, like I think I came across how I wanted to. Right. You know what mean? Like having experiences like that kind of builds it. Okay.

Does success, and I'm saying success is like a loose word, does having success with girls previously lead to confidence for you?

Speaker 1 (26:32.876)
Like you've had successful meaning like good dates or no, I'm saying like you're long like a relationship. Yeah.

Like dating I don't I don't think so I because I genuinely believe that like confidence comes from you. Okay, I Mean, I think you can I think you can I Think that's where cockiness comes from. Honestly, okay is like good differentiates Like how you think others perceive whether it's like a relation like what did other people think of this relationship? Right, right, you know, I think that like confidence is between you and you

You don't think it can cover anything else.

Speaker 1 (27:07.086)
Yeah. Yeah. I think that's great.

Yeah, cool. Like I think that you got to do a little bit of like, yeah, introspection. Like I think it starts with like, what do you care about? Like, what are you passionate about? Yeah. The more you know about yourself, feel like.

work on yourself to

Speaker 1 (27:21.474)
And I think the more time you spend with yourself, the more you become more confident. Cool. Good answer, by the way. Yeah. Where were we? I don't know.

Yeah. you.

You have the mystery text or question list

I missed my mystery notes app. I want to talk about we I mentioned relationships briefly and I want to talk about like breakups. How do you? How do you deal with a breakup and what advice do you have for somebody that's going through a breakup?

Okay. You're like, okay.

Speaker 2 (27:52.552)
Ooh, how do I deal with a breakup? That has evolved over the four relationships I've been in in my life.

Which is a really good amount. Is it? I mean, I don't mean that in like a, you know what I I don't know. I think it's like a, the word's not impressive. I feel like trying to this. I'm trying to say it correctly, but like also mean what I'm trying to say. I've only been in one real relationship.

I don't know

Speaker 2 (28:13.25)
Love watching you just struggle

Speaker 2 (28:21.08)
think I understand what you're saying. So it's hard to gauge what went wrong. No. No, I'm kidding.

Yeah, I agree like I only have my takeaways from that one relationship and like realize there were things I did in that relationship that were wrong Yeah, and bad, but that was like four years ago. Yeah, like Yeah, I've changed so much as a person since then a lot of it from that relationship, which I always say like Any like time you spent with somebody like whether it's like a year six months like you always learn something about yourself from it I learned so much about myself, but that was four years ago. So like

and you haven't learned anything about yourself since.

Not one thing. not one thing. Damn. No, but I mean like so okay, you've been you understand what I'm trying to say at least.

I understand what you're Yeah, dealing with them

Speaker 1 (29:08.236)
And which one was your favorite? I'm kidding. And who do you hate the most?

We're not gonna do that. No, honestly, talking about dealing with them, my high school relationship absolutely crushed me. My first relationship. And I think honestly, like a lot of it was, I didn't have like the closest knit group of friends in high school. I had some, I have people from high school that I'm still close with now. They were kind of in different groups of friends. Just didn't really have, and I think that like,

That's never a good recipe to go into a relationship with if you don't have like that core group of friends. You know? Senior year. Okay. 18 years of age.

age was this and what year of high school?

Speaker 1 (29:51.064)
but like senior year to college.

Okay. Yeah. I think that honestly the most important thing in dealing with a breakup is kind of like what you said. Like you need to do some retrospection on one like what went wrong. What did you do wrong. Right. Because every relationship anyone's ever been in both people have done something wrong. 100 percent. No one's perfect. There are things that both people did incorrectly that kind of led to it. Totally.

But I think that it's like a good time to just like focus on, again, like kind of goes into the confidence conversation too, but like, what are you passionate about? Like find something, especially if it's, if you were the one that gotten broken up with and like you're feeling really down about it, I think the toughest thing is like, I spent so much of my time talking to this person and like having this person in my life, like how do I fill that time? Cause it's like, it's like a void there.

And so I think whether it's like, think the gym is a great one or like going for runs. Like we said, like I think that's a great way because it's two birds, stone. You're doing something that's benefiting you and you're also not, is that a timer? That's the camera. the camera.

Keep talking. It's such a good conversation though. Keep talking. Hold the mic. Go ahead.

Speaker 2 (31:08.79)
Okay, but I think it's a good time to just think about What you're passionate about what can you improve about yourself Whether it's the way you approach relationships or just in general I think that that's a good way because it's so cliche I was actually just talking about this with a co-worker of mine It's so cliche, but it's the most true thing ever The only thing that heals the pain of a breakup is time right like literally that's the only thing

The camera might have died, that's okay. They lost the vision. Bye YouTube. It's been real.

No, that's okay. It's fine. We did our best. We did our best. could. No, but go ahead because this is a really good conversation.

Yeah, I mean, I think that that's that would kind of be my biggest thing is Oh my god, don't pull up the questions on now. You're see them. can't see Okay, my gosh was that just pointed at my crotch like this the whole time Okay. Well, we'll get that in post-production

I'm gonna film on my phone now.

Speaker 1 (32:06.734)
Okay, it's a little low. Should I raise it?

Sorry.

I'm like covering night Down goes down goes the light. Yeah, that is good

hold on. Quote this, one day I'll be in a real studio.

Yeah, that'd be cool. Next apartment have like a little studio.

Speaker 1 (32:29.742)
be like this makeshift for now for now it's janky as hell and I kind of like it's okay we were talking about relationships you were you say what you just had

Now we're

Speaker 2 (32:40.69)
Time of introspection. Yeah. Well, I think it's important like I think it's a it's a good Like breakpoint in your life to be like, okay, let's check in on me. Where am I at professionally passion-wise? Right physically like health-wise. Yeah, I mean like I think it's a good time Especially if you're like eventually gonna go out and start meeting people again

That's true. Are you comfortable going into the high school relationship or no?

There's not much there.

Were you, like you said, like if you were one broken up with, can I ask why or like what, you're like, you can say no to.

Yeah, I got broken up with.

Speaker 2 (33:17.27)
Yeah, I mean, just, I feel like there's not really a lot, like to me that's the least relationship out of all my relationships.

But like, why was that one the most gutting, you said?

Cause it's first one. Okay. And also, like I said, there was no fallback group of friends. I felt really like I had some people that I could talk to, but like it wasn't like, like now I feel like I have the support system. Like I have the support system I needed. Right. For that.

So it was like a very obviously lonely isolating like. Yes.

That was more of a situ- it really had nothing to do with the relationship. It more like the situation that I was in after.

Speaker 1 (33:48.97)
Was there one relationship that you learned the most about yourself from or learned about like that? did something in that you wish you hadn't you know what mean? Or go stay with the first one like what you learned

I don't know it's hard to put like a number on it. You know what I mean? Right like I learned X amount

I don't mean like I mean something not like what you learned. mean like

I think that the most, you learn things about who you're compatible with. Like, whether, or if it's things that don't work for you compatibility-wise. I think you get that out of every relationship. Like, these were the parts that I liked about it. Like, this is what I need out of a part. Because it's a back and forth in a relationship. And like, these are things that I can't.

Okay, that's a good one.

Speaker 2 (34:40.928)
if this is something someone's going through or like, not even gonna say like personality traits, but you find like what's compatible with you and what isn't. Like I think that's kinda.

Is there something you realized that wasn't compatible with you? Or that you weren't compatible with?

Speaker 2 (35:02.382)
I don't know specifically, I also don't know, I don't wanna get too- No, it's okay. Okay. I don't wanna get- It wouldn't be a podcast episode if you didn't spill something.

Fine, that's fine. Sorry, sorry,

Speaker 1 (35:12.994)
Good time to switch topics. Okay. Thank you for being vulnerable. I appreciate it. course. It's important. I think it's like, it shows that like we can have this conversation. So like if another friend or somebody is feeling the way that you had felt or yeah, it's important to get into that type of shit. Absolutely. It really is. Okay. Where, talking about confidence, like how do you dress? Where do you shop for clothes? yeah. What do you, what do you look for in an outfit and how do you, what do you wear on a first date? I asked you like four questions.

Absolutely.

Speaker 2 (35:41.856)
Wow so many okay first question is Okay, that was the last question, but know It's evolved okay, it's evolved. I'm sure you've noticed I've become gene guy Yeah, I never wore jeans I just thought they were I thought they were uncomfortable So comfortable and then I went to Levi's and I got straight jeans because I just didn't like the skinny jeans I think that's what it was

What do you wear on a first date?

I'll start first.

Speaker 1 (35:54.594)
Yeah.

Speaker 1 (36:01.058)
There's.

Speaker 1 (36:06.582)
I think it's it's it's finding like your fit. Yeah

Yeah, it's really important. I went a little bit up in the waist and wear a belt. Which is great. Yeah, I will probably wear these on every first date I go on from now.

So jeans and like what's the top?

It varies, depending on the weather.

Let's say it's like now, right now it's fall, fall slash winter. how'd that go? Where'd you go?

Speaker 2 (36:29.954)
I went on a date today. went well. I wore... We walked along the Hudson River. Yeah. It was a walking date.

Okay. So it was like a walking date. What number date was this?

Okay, and then we got food Went to a diner. Yeah But I wore I didn't wear this well I wore the jeans But I wore a staple Outfit well, I guess staple general fit which is jeans and a shirt that I bought on Etsy. Okay. Yeah, I wore my Justin Bieber mugshot

And what'd do for the first day? Nice.

Speaker 2 (37:12.982)
On a date? On my date today, Did you?

That was second date and like she got to know you more. Yeah, right

She knew I was a little I don't it's not gonna say weird but She saw me in that and actually didn't question it at all She just kind of like looked at it laughed and was like yeah that that makes sense

Hahaha

Speaker 1 (37:29.006)
in the first date.

Speaker 1 (37:33.178)
If you're going on a date tomorrow, would you wear? First.

something similar. no, I wouldn't wear a t-shirt. I haven't been going on a lot of first dates recently, so I'm-

So I think I would wear like a button down shirt or a button down shirt like with a t-shirt.

do that. Now that I think about it, I might go weird t-shirt. Really? Yeah. I think that that's another thing I wanted to mention in the first dating section too is don't take it too seriously. Yeah. Yeah. And it kind of goes in because I think that's how you like manage feeling confident and like not being nervous. Right. It's like, wait, you don't know this person. If it goes horribly, it doesn't matter at all. Like it's and it's so much easier said than done too. But like

It's such a good-

Speaker 2 (38:15.104)
Really, like, you're just meeting somebody for the first time. It's not, you're not going on a, well I mean I you could be going on a first date with your wife, but like, I don't know, I think that if I go in with some wacky fit, like that's more of representation of me than anything.

like you, like why should you like that?

Like if they don't if they don't laugh at that shirt and make a comment on it like we're probably not gonna get along So I think I think it comes down to and this is like kind of going into your other questions as far as like dressing like Looking in the mirror before you go out and be like this is how I want to present myself. I look good Let's go get it. Yeah

person for you,

Speaker 1 (38:57.176)
Yeah, love that. Yeah, yeah, that's really important. Where do you shop?

kind of all over. I mean, I've been on the Etsy t-shirt grind recently. I've got quite a few of them and I think they're fun. This is Malbon. Nice. Fun brand. Golf brand. Way too expensive for me to like it as much as I do. It's a good fit. Thank you. Levi's pants. You were with me when I bought these. where else do I shop?

Pants

Speaker 2 (39:27.758)
That's kind of it. I did a big Nordstrom run. It my mom's graduation gift to me. It's a good one. It was just a bunch of professional attire from Nordstrom. She got me a tailored suit.

Oh, what do you want to work?

college shirt

Not button down. You don't like required.

No. No, it's pretty casual. I wear Jordans to work. I wear some form of khaki, like black khaki colored or gray pants, like some form of khaki material probably.

Speaker 1 (39:49.247)
Yeah, yeah

Speaker 1 (40:04.686)
Any of the odds on the fashion tips? Fashion advice?

no, I think that's kind of it fashion wise. Okay.

So Luke, this is the fast question section, which is a new section for this podcast specifically. How excited are you that you get a new section? First question, do you have a skincare routine? And like these questions are supposed to answer like one minute-ish.

Okay, the answer is no. Yeah, but I also, this is such a, I'm not gonna say cocky, but annoying thing to say. I have very good skin. Like I don't really break out ever.

Ever. Well, I wish I could be you. Yeah.

Speaker 2 (40:48.862)
but I should, it's funny. I have an article, I have a browser or a tab open on my phone. Okay. GQ article skincare routine. Cause I've been meaning to do it. Cause I think as I get older, like there's no reason to not have one and like, don't want to wrinkle. Yeah. It's going to get skins important. It's going to, it's going to not, yeah, it's not going to be good forever. Right. Okay.

Gettin' skin like, yeah.

Speaker 1 (41:06.722)
Do you like give a shaving routine? What do you use to shave?

I go back and forth sometimes I use a blade I go clean shit

What brand of sh- like what stuff?

Harry's. Harry's razors. I got a bunch of them for Christmas. Just standard shaving cream, nothing crazy. I have an electric razor I'll use on my face if I want to have like some stubble. Okay. And not go clead shave, but...

What do you use to shave your member? You're down there. You're downstairs area. Manscaped. Manscaped? Yes. 2.0? 3.0? 4.0. It's 4.0? Okay. I also use Manscaped. No, that is like a really great brand and like...

Speaker 2 (41:33.602)
My member. My downstairs.

Speaker 2 (41:43.438)
Yeah, I just upgraded. 2.0 died. sponsor.

Speaker 2 (41:54.03)
Advertising's funny too. The power of marketing.

Also, it's funny the power. But also the flashlight on it, I think is really important. Like if you use that. Yeah. Okay. You don't think it's like, I think it's like a revolutionary.

No, I don't think it's... Like best thing since sliced bread. The manscaped flashlight.

I like actually think it's- what condoms do you use?

Trojan Ultra Ribbed Yellow Box

Speaker 1 (42:17.718)
And have you ever tried different ones or is that always the one you've gone for? That's what I said in the last one, I said I've always used it.

is the one I've used. If it ain't broke, don't fix it. You know?

If it ain't broken off, is it? Literally. Okay, how often do you wash your sheets?

Speaker 2 (42:33.89)
I just made a comment about this after your episode. I don't watch them as much as I should. I should watch them like at least like once every two weeks. I'm probably closer to two and a half, maybe three. It's bad.

I'm the same way though. Like I'm sorry. Let's be honest. It's gross. Let's be real with ourselves and How you want to do apartment? is this is a different section now about it Move departments did which is the kind of final thing we're gonna talk about. Yeah, so let's get into it. Okay Let's rip it. So you lived with three two roommates free Shout out Kenny and Pat Patrick and You decided to move out what made the decision to move out?

Yeah.

Speaker 2 (42:55.214)
I did

Speaker 2 (43:05.966)
Tourbates. From school. Shoutout Kenny and Barb.

Speaker 2 (43:16.91)
Yeah, well, yeah, so as you said purchased an apartment Yeah, which kind of fueled the decision to move out. I probably would have stayed another year if I wasn't gonna do that. Okay and the reason I purchased an apartment is because I Realized I want to live here for a while right in New York City, York, New York, I realized I want to live here and obviously makes more sense to Put equity into a place. Yeah rather than

Yes.

Speaker 2 (43:46.222)
because rent is essentially setting money on fire. I don't agree with that, but... No, it is.

they know I know but I okay we'll talk about your years and then we'll talk about me okay this is about you this is your

This is my episode. I'm the star.

So how did you go about buying a place?

So four steps, four main sections. First is a search, you gotta find one. And that took me about two and a half months to find one I liked that was in my budget and in the area I wanted. I was pretty much only looking at doorman elevator buildings because they hold their value better.

Speaker 1 (44:33.16)
nice amenity to have in the city especially when you're getting older.

Really is nice. It really is. I made fun of people for having a doorman in an elevator. I was like, I can climb stairs. And then you climb stairs all the time. You're like, damn, this sucks. And doorman is great for packages and stuff. Also saying hi to somebody every time I walk in is really nice. All my doorman are really nice. search. So I actually found an apartment and

with grocery bags? Yeah.

Speaker 1 (44:58.913)
Yeah. one.

Speaker 2 (45:05.71)
like picked one out that I liked. had this like really cool street level outdoor in. It was awesome. was the garden was so, so.

Skated. Okay, okay. Yeah, no, it was nice. It looked really well maintained. Okay. And I don't really see any rats by where I live. I think that's just down here,

Yeah, I really hate to break that to you. it's grimy down here.

Yeah, no, yeah But so I found this apartment it needed a lot of work, but it was pretty cheap, okay and That comes to step two which is negotiation Which was an interesting process?

Yeah, I'm just gonna say numbers because it makes it easier to talk about. But so I was looking for stuff under 400,000. Okay. That was kind of my goal. And there's not a of doorman buildings with an elevator that are under four fat. Yeah, like that's pretty rare. And so there were two that I found. So I found this first one with a garden that I really liked. Okay. It was listed at 395 and it was kind of a piece of crap.

Speaker 2 (46:16.674)
So my realtor and I were like, we're gonna come in a little lower than that. Okay. And we'll work our way up to around 350, 360ish. So we came in at 330. They countered in negotiation with 390. So we're very far apart.

Got it.

Speaker 1 (46:29.998)
Very very far apart

it was just not, you could tell that the vibes were not good in the negotiation all the way. Like we jumped a lot more after that. We were like, okay, 350 and they did like three, three 80. They were not moving at all. Yeah. So we wound up agreeing on, so I came back, like there was a back and forth, back and forth. cause again, it's still a good deal.

so they weren't budget

Speaker 2 (46:58.862)
Like under 400,000 for the building that I got still felt like a good value, but it was like kind of sour in the negotiations. Like it was just not great. And the real estate agent was kind of a slime ball. And we wound up agreeing at 380. My real estate agent wanted to get to 375, like 5,000 as like a gesture of good faith. Like we came in at 370, they were at 380. He's like, let's just meet in the middle. And they were like, no.

Yeah, it was just it was just

like for 5,000, which is a lot of money, but like in the grand scheme of things of what we're doing, like as far as my mortgage payments and everything, it's not that much. Like it's just a matter of like, yeah, like we engaged in negotiations. Let's meet in the middle here. So then step three is the co-op. Okay. And it's a co-op building. Most buildings in New York are co-ops and condos. Co-op essentially just means that the building is owned by like a corporation. Okay. And so they handle like,

Cleaning the building they pay the doorman like all the maintenance around the building is handled by the co-op They pay your property taxes and in return for that you pay like a monthly HOA fee homeowners association fee And so that kind of goes towards your taxes towards the building being maintained whatever got it And you need to get co-op approval a lot of them you have to apply how's that work this you

I'm just gonna keep telling it in the story of like my experience. So the building that I originally agreed with the garden, they wanted my monthly mortgage payment plus HOA, so my total monthly payment for all my living, to be 25 % of my income, which in New York is pretty hard. Like rent and like the mortgage is expensive. Like I'm not making a ton of money. So to get to 25 %

Speaker 2 (48:53.486)
Like that's pretty difficult. Yeah. So my real estate agent and I were trying to find ways to like kind of game that a little bit. Okay. And at this point I was kind of getting fed up. Like it was pretty crappy negotiation and now they were throwing another hurdle at me and I was like, this is just silly. So then we looked at the other one, which is the apartment that the other one under 400,000, 400,000 that had the elevator in a dormant. Okay. And which is the one I'm in now. And that one was listed at

when you're in

Speaker 2 (49:24.382)
350. Okay. And we came in, we were like, let's go in at three 40. Cause we were like, that's good value. Honestly, let's come in at three 40. They'll probably meet at three 45. We came in at three 40. They said deal. Oh great. So immediately vibes better. Yeah. So much better. Yeah. But as far as the co-op application from there, 60 pages of every

bit of information on you ever. my god. Bank accounts, paychecks, 401k, background checks. Everything. Right. Literally everything. So that process took a bit. I interviewed with the co-op. Basically I think they just wanted to find out that I wasn't some crazy person. Yeah. Okay. Very chill. Yeah. I applied my interview tips from earlier. Yeah? Yeah. No, I just...

crazy

Speaker 1 (50:04.494)
Was that like on Zoom?

Speaker 2 (50:13.656)
treated it like a conversation. And then I got approved. And then the last step is the closing, which is the part of this that took the longest by far. Essentially that co-op needs to provide the bank information, the bank that's giving me my mortgage.

Which is important. It was very, very chill.

Speaker 2 (50:42.648)
basically that shows like all the co-op's expenses, like the co-op's mortgage on the entire building. And getting that information from the co-op took forever. Shout out our friend Steve, who moved into my room in my old apartment. I was subletting from him while this took forever and also traveling four days a week for work while trying to do this, which was horrible. No.

That's not.

Speaker 2 (51:11.958)
So shout out Steve, you're the man. But I brought a prop. It's the closing, the actual closing. I had to sign a ton of stuff and I get copies of everything. my real estate agent slash attorney put this together for me.

Oh! We have a prop.

Speaker 1 (51:35.767)
I've never seen this before. is never before.

So this is everything I had to sign. I'm showing it to the camera for YouTube. Yeah, he laminated and bound it for me and put together a table of contents. Did you read it? I mean, I signed a bunch of it. And as I'm signing it, he's basically explaining it in simple person's terms what I'm actually signing. Like I very well could have. That's the reason you need an attorney for all this because the amount of-

Holy shit.

Speaker 1 (51:51.116)
all this?

Speaker 1 (52:03.56)
stuff. How did you go about finding your real estate agent? Holy fuck.

Family friend. Okay. Has a lot of property in New York. He was amazing. He was my real estate agent and my attorney. does both. Amazing. Yeah. So he was absolutely fundamental to the process.

And then how did you go about getting the money to put down the place?

Yes, so New York apartments 20 % down. Okay, that's a lot of money No, okay, that's way more money Considering how many drinks I buy every weekend at st. Infant how many dates the eight rum and Cokes I have at st. Infant as every weekend would not have allowed me to save 90 grand in a year, right? so I'm very lucky my parents Once they found out I was serious about it

be able to put that on your own.

Speaker 2 (52:49.782)
Yeah, like they wanted to know that I had a plan that like I was really doing like I was finding a value like I wasn't just impulse buying an apartment right right right like and you know me and Some people listening to this might know me. I'm a terrible impulse buyer Bulls by us of all time, but I did I put a lot of work into finding this place and making sure that it was What I thought was a good deal and what he thought was a good deal So once I kind of presented that to them, they were fully on board and the very supportive and thank you

you guys are listening.

Your mom doesn't listen. She's gonna email me questions before I told this about Deb Okay, yeah that sounds like an insane process how how is living on your own because that's something like I've thought about that I want to really get into honestly Like living alone versus living with two roommates and in craziness like how's that?

Yeah, it's nice. Yeah, I really like it. Yeah, it's I think it's something that I've it's kind of changed about me since college. I think like as far as recharging my social battery, like when I'm like tired from like a weekend out or whatever. Right. In college, I would want to do that by like lounging around with my housemates. Yeah. And like watching football, right. Doing whatever and like bantering. But I think post college, I think I found that I like to kind of do that on my own. Yeah. Recharge.

And so it's been really great for that just to have my own space. Also living in New York, when you have roommates, chances are you're living on top of each other because these apartments are so small. Like this apartment is fantastic compared to our apartment. Like our apartment is just so goddamn small. And yeah, I think post-grad I've come to realize that I...

Speaker 2 (54:39.707)
like having my own space, like just by myself a lot more than I did in school.

think the biggest thing like post-grad versus in college is realizing that type of stuff by yourself. you need more time to recharge. I mean, let's talk about like the amount of we used to drink in college versus now. Like now we drink maybe, or go out. I'll say go out because whether you're drinking, No, but like drinking aside, like you're going out Friday, Saturday, maybe Thursday with coworkers, maybe Wednesday with coworkers. in college, like.

As I kill my twee.

Speaker 1 (55:13.43)
Every day was something. So the life is just totally different now. And like, I think that transition period was a wake up call for everybody. Like, I think I transitioned well, but like, there's still moments where I was just like lonely or like, thought it was like, gonna be way different or like thought there was always be things going on or people to see like, it's not how life is anymore, which is okay. like,

Yeah, there's something going on.

Speaker 2 (55:22.798)
episode.

Speaker 2 (55:36.034)
Yeah, that's definitely different.

Anything else you want to add to the people? That's all my questions for you. We've gone off for a while. It was a really good conversation.

Yeah, we've gone over so Lee yeah, no, I think that we touched on a lot of stuff. This was a lot of fun. This was great. Yeah, I had a great time Yeah

being on no this is like really really good yeah very conversational as you said about an interview feel like an interview at all no I said did it feel like I was like no no Luke did you hear what I you grill

That's yeah, this was yeah, it did totally. For two and a half hours. Get me out of here. No, it was a lot of fun. This was great.

Speaker 1 (56:13.026)
Thanks for being on here. Yeah. People are gonna love this one.

Do I get to like hear the outro music or does that come on in my ears or anything? I'm kind of disappointed that we didn't get it beforehand like... BOMB BOMB like I was gonna get all hyped up.

later.

Speaker 1 (56:29.166)
I should have played it you before. If you didn't have as many technical issues, would have that. Part two, when you come back. So that concludes part one and part two of my interview with Luke Lenny. Thank you so much for listening. I really hope you enjoyed it and thought this conversation was as good as I did. If you liked this podcast, please give it five stars and leave a positive review and like it and subscribe wherever you're listening and come back next Tuesday. I will see you guys. Oh, wait, sorry. I think I forgot to say to leave this podcast five stars and positive review.

I had to that in. Also check out the Instagram and TikTok at the guy set and send it any questions you have for me to my email. Josh J O S H at guyset.com G U Y S E T.com Josh at guyset.com and I'll be sure to talk about them. Thank you so much again for listening and I will see you guys next Tuesday. See you guys.