First Date Tips for Guys (What to Do Before, During, and After)

Josh Felgoise (00:00.398)

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.

Josh Felgoise (00:17.614)

Hi guys, welcome back to guyset, the guys guide to what should be talked about. I'm Josh and today's episode is a highly requested topic, which means that at least one person requested that I talk about it. Because when I say, let me know what I should talk about and I'll be sure to talk about it. I do actually mean that. So let's get into it. Let's talk about tips for going on a first date. Think about this as your first date guide. And I'm going to go in order from the start of like planning the date.

sending texts, figuring out where to go on the date, how I get ready for a first date and kind of prepare myself, what I'm wearing on the first date, two topics to talk about and follow up after the date. And I'm gonna get really detailed and transparent into really what I do because I don't think there's enough out there right now for guys to hear other guys talking about this type of stuff. And that's kind of the mission of what I'm doing. So yeah.

If you listened to episode four of the podcast, and if you haven't, you should go back and listen. It's called, Let's Talk Ghosting. it's kind of the aftermath, or it is the aftermath of what happens after a date or a couple dates or relationship situation, situation ship goes south or one of you stops talking to the other person. And I kind of wish I started with this one because this is a much more positive note about going on first dates and starting out dating, but

I didn't and that's because that's how I was or that's what I was going through that week and this is this week so I'm gonna stay honest with you guys always and I want to start with mindset and mentality going into a first date. I think it's really important to go in with an open mind and a fresh perspective when meeting somebody new and this starts with not googling the person not checking out their social media profiles

or doing a deep stalk of the person, their siblings, their family, their job. I think it's so much better to go into meeting the person for the first time, just seeing if it's a profile on hinge, just seeing their pictures and what they wanted to present to you. Or if you met at a bar or however you met, just knowing that piece of them. So you come in with an open mind.

Josh Felgoise (02:39.854)

and you don't think, oh my god, they went to that school, they're so much smarter than me already, or oh shit, they have that job, they're already doing better than me, and you have these preconceived notions of all these things that they either are better than you, or you're better than them, or just the things that you don't need to go into a date thinking. So my first piece of advice is to not do that. Because how much worse is it if you already know who their ex-boyfriend is, or what...

they ate for lunch today, like it's just, you don't need all that. Just go in with an open mind, go in with a fresh perspective, and be excited about it. Also, half the shit you're thinking is probably not even true, so you're making up things in your mind before you've even met the person. So I think you have to give them the chance before you make up all this shit about them. Also, I want you to know that when I say you, I also mean me, because I've done this shit too, and I've made stuff up about people in my head before I've even met them.

and that puts them back a step and gives them less of a chance. So I do this stuff too and I'm working on it as well. This kind of follows along with that piece of advice, but I think half of the battle is how you're feeling before. If you're excited about the date or at least excited about the opportunity or the possibility of the date, then I think you're already

in better headspace than half the people going on a first date. So come into it with a good mentality. If you think it's gonna go badly, it is going to go badly. That's called the self-fulfilling prophecy. If you think it's gonna go well, you have a better chance of it going well, or at least enjoying the time a little bit more than you would have. If you're going into a first date thinking, this is gonna be terrible, this isn't gonna be fun, she's not gonna like me, I'm not gonna like her, you're not even giving yourself a chance, you're not giving her a chance, you're not really giving

the date a chance. why even go on the date at that point? So first, would say mindset is most important. If you have this shift about the possibility of the date that it could be a good thing, it could be great. And you don't feel like it's going to be a shitty time and you're not so anxious and nervous about it. That's the start. Let's talk about when we're going to go on the first date. So I always prefer a first date during the week. I think it's so much less serious than a weekend.

Josh Felgoise (05:06.648)

I kind of reserve my weekends for time with my friends. I mean, look, like not every day it's gonna go so well. So if a day that doesn't go well, at least it didn't ruin your Friday or Saturday night. And if the first date goes well, then you can go on a second or third date on a weekend night because then you're really giving that your like your weekend to a date and that feels more special because it is. So I recommend going to a first date after work on the weekday.

I personally prefer a Wednesday or a Thursday night, but that's just me. But take that if you want. And otherwise, Tuesday is fine. Monday, I feel like everyone's tired on a Monday. We've talked about our mindset going into the date. We've talked about which day might be best during the week. Now let's talk about where we're going on the first date. So personally, my ideal first date is going to grab drinks. I think it's super easy to send a text saying, Hey,

Would you want to grab drinks this Thursday at 730 at X place wherever and I like to try a new bar either by me or by where she is I think it keeps it fun by going to new places. It gives you a new conversation topic It doesn't keep different dates feeling stale or boring Plus that's already a built-in conversation topic if neither of you have been there or it just gives you it just gives you a conversation topic right off the bat

We'll talk about a lot more conversation topics and things you can talk about on a first date later, but we'll get there. And the reason I think drinks is a great first date is because like the mentality of a weekday, there is no pressure behind it. If it's not going well, you had one drink, so what? It was 30 minutes to an hour. And if it is, you get another drink and you get to get to know the person and relax and just have a good conversation.

but there's no pressure of sitting through an entire dinner and an appetizer and an entree plus the amount of money that dates cost. Like I've spent like 70 bucks on a date with just getting two drinks each and this is in New York city. And I called my friend after that date and was like, holy shit, I just spent so much money. And he was like, how much you spent? I told him that amount. And he was like, and I was like, fuck, I'm, I'm in for a ride here. But the amount of

Josh Felgoise (07:29.092)

money it would cost if you got dinner at every single date that would be absolutely fucking crazy. So the money element plus the lack of pressure is why I'd recommend getting drinks on a first date. It keeps it casual and chill bro so like yeah. Other alternates if you don't want to go grab a drink I'd recommend going to grab a coffee or going to some sort of like chiller food thing. I did a like walking

cookie tour with this one girl and I thought it was a really good date. was my friend's suggestion. We basically walked to like four different cookie places and tried them out and compared them. And yeah, I something like that where it's not so much pressure as sitting down for a four course meal and wearing a top hat, like something relaxed, chill. I was gonna add in that like you could go for a walk on a first date, but I feel like that doesn't give off the right vibes.

and could be perceived as weird. I feel like adding in that element of going to do something like go test out a couple cookies or go try a new coffee place or check out a museum or something that you can walk around and talk, not something that you're sitting down like a movie where you're not going to get to know the person, but finding a common ground that you can talk to the person with the backdrop of some museum or statue garden. I don't fucking know.

Ultimately picking a first date spot is really hard. think you go with your gut. If you want to grab a drink and do something casual like that, it's great. If you guys bonded over something that you could go walk around and do or see, that's also great. I think like a mini golf type of thing is really fun. Bowling could be fun. An activity that you guys would both enjoy and can get to know each other through. That's great too. I think any of those are good options and that's a good starting place for you to start.

Drinks is just easiest for me to get to know somebody, but maybe that's why I'm getting ghosted. And maybe I should do more of these activities that I am talking about here. For anybody listening, let me know what date spots, what first dates you go to, what places you recommend, and I'll share them with the rest of the community here, because I think this is something we put a lot of pressure on and realistically shouldn't because we haven't even met the person yet.

Josh Felgoise (09:54.318)

But understandably so because we want to give a really good first impression. yeah, I also like to be confident in when I ask for a first date. I kind of laid it out before, but I'm going to do it in another way. So here's how I would phrase the text. Hey, Anna, how's bowling Thursday night at seven thirty question mark. I think that kind of gives a confidence to you. It feels affirmative and it's not like, hey,

Would you wanna do drinks or would you rather grab a bowling ball or we could go bowling on Friday or grab sushi on Saturday or eat a sandwich on Sunday or blah blah blah blah. I think this gives off the perception of confidence and that you know what you want early on and you're already setting yourself up as not the guy who can't decide between pizza and sushi. So it's a good start. Now we've talked about possible first date options.

and a way to phrase a text asking to go on a first date. So let's talk about how to stay excited and in a good mindset after a work day or going into the date after a long day. I feel like a lot of the time after work, I can feel pretty depleted or tired and my energy levels are much lower at like a five or a 536. But the way that I kind of keep myself going is I will

think about it during the work day and try not to fall into that depleted or tired state. I'll maybe walk home from work instead of taking the subway. I'll put in some like pump up energy music and I'll kind of keep that going until the date. Usually I feel like a first day is probably what seven or seven thirty. So there's not so much time that has to pass between work and the date.

but during that time, like I wouldn't go take a nap. wouldn't, you don't need to like go sit on the couch and get tired, but yeah, stay in that energized state. Let's talk about drink before a first date. I personally like to have a little Bev before a date. I think it eases my nerves a bit. And this is nerve. This is, it's a nerve wracking thing. We haven't gone into that yet. I will get into it more, but going on a first date.

Josh Felgoise (12:13.25)

is a nerve wracking thing. It's always going to be you don't know the person that well. And yeah, just meeting somebody I said this in the ghosting podcast episode, but meeting somebody for the first time and just putting out everything you have to offer and talk about yourself for them to kind of judge you and decide if they like you and they want to fit into that into what you're presenting. It's when you when you put it that way. And when you think about it that way, it it's scary.

But there's no need to think about it that way. Think about it as a fun experience to get to meet somebody new, get to learn something about yourself, learn something about the new city that you're in or wherever you are, learn something about a new restaurant, a new drink spot, go try a new drink, talk about something different. There's mindset shifts that you can bring into it that take you out of the, fuck, I'm gonna go tell this person all about myself and then they're gonna decide if they like me. Shit, I don't wanna do that, but.

Instead, think about it as a new experience and if anything, a new story to share with your friends. So I'll personally have a beer or like a half shot, just something small, nothing that's going to like get you overboard. If one of my roommates is home, I'll ask them to take the shot with me. If not, I'll do a solo shot, whatever. It's just something that eases my nerves a bit. Doesn't have, you don't have to do that. I haven't done that before every single date. I'm not an alcoholic.

But yeah, it's my, I like it, whatever. I wanna share these things with you to be transparent about what I do before a first date. I feel like there's not enough of this out there and that's why I'm sharing. And I have made a playlist on my phone called Predate. And some of the songs in there, this is incredibly embarrassing, but some of the songs in there are I'm a B by none other than the Black Eyed Peas and.

demeanor by pop smoke and do a leap and you get the picture and not to share anymore but the recommendation here is to make a playlist of songs that you love that hype you up to get you pumped to just get you excited for the first date. Side note this music hype up thing also works for any other date as well as like a big presentation at work or something that you're worried about and nervous about you got to hype yourself up for this works for me I can recommend it more. I love it now on to.

Josh Felgoise (14:33.332)

The question I always wonder about and I always like I'm nervous about and worry about is what we're wearing to the first date. So I personally think you can never go wrong with a button down pants and like white sneakers, some sort of like casual shoe. I am lucky enough to live with two roommates who I can run out into the hall and be like, does this look good or does this look stupid as hell?

But I think I mean I've also sent pictures like a friend or something and been like hey like how how's this fit? So I recommend doing that too just to like check it up with somebody But I think you can't go wrong with that sort of fit. I think it looks good. It shows that you put in some effort You're not rolling up in a t-shirt. I think that's a bit too casual, but this is just my preference This is what I think I would love if any girl is listening to this to let me know what they think

of a first date fit for a guy. But yeah, I think this is a good look. Also for the guys listening, let me know what you're wearing to your first dates. I am always wondering what I can be, like how I can be elevating my style and I think other guys are wondering the same thing. So I'd love to make a kind of fit guide for first date outfits. To get even more detailed, I usually wear a navy button down and khaki pants or

A like white button down with dark jeans something like that that just looks clean Easy it's simple. We I know it matches so that I'm not gonna clash and Yeah, it looks like I put in some effort. I said I also don't button the buttons all the way up to the top like I'm to go fail a job interview So I'll usually like unbutton a couple a couple buttons. So Sexy if I have enough time, I'll also shave before the date

I feel like again it looks clean and that I've put in some effort to the date. I'll spray on some cologne, I'll put on deodorant just to smell good. Probably chew a piece of gum or two on the way there so that my drink tastes like shit but my breath smells good. Yeah, those are a couple more like little detail things that I do. So now for when you're going to the date, I usually try to get there.

Josh Felgoise (16:53.718)

10 to five minutes early. I won't try and get there so early that I'm sitting there anxious about when she's gonna get there. I feel like girls, or at least in my experience, are always late to the date. I feel like I've always gotten a text that's like, hey, I'm running late, forgot my wallet, or hey, like running five to 10 minutes late, and they usually show up like 10, 15 minutes late, no matter what. That's at least in my experience. I did have one date that she got there.

5 minutes before which you can't control that's gonna happen but I think a good rule is like 5 ish 10 ish minutes before the date is called for I mentioned before time for a date but I do think the best times at least for me have been like 7 7 38 because you usually have one drink to two drinks if it's going well and it's about like an hour and a half to two hours and I think yeah by like 10 on a weeknight is a good time to end

When waiting for the date to arrive, I try not to be on my phone when I'm at the restaurant. If in the case she walks in and I'm on my phone, I feel like it already sets a bad vibe or a weird vibe because I'm not thinking about the date. I'm thinking about whatever I'm scrolling on. I also feel like the mindless scroll for me just like takes me out of that head space. I've already like worked hard to put myself in and I'm thinking about someone else's like

corn salad they made on Instagram and I don't really want to be in that mindset. So I'll try to stay present, like look at the restaurant, maybe look at the menu, that type of thing. Of course, if she's arriving so late or you're waiting for a while, I think it's fine to go on your phone, but try to keep looking up and being aware of when she's going to get there. Now let's get into what to talk about on a first date. When I on my first date,

I feel like my first New York City date after I moved, feel like it was around like November maybe. I texted one of my friends, was like, what the fuck am I supposed to talk about with her on this date? I just like, for some reason you forget that you're human when you're meeting somebody new sometimes. So I think easy topics that you can always go back to are talk about the area she lives in, talk about her job, your job, your roommate situation.

Josh Felgoise (19:16.404)

what restaurants you've tried in your area, what asked her what restaurants she loves the most in the city or wherever she is. The bars you both like, TV shows, movies, music, podcast, books. Those are always good topics to bring up and like can get a conversation going whenever. So when you feel like you're nervous that there's too much space or that you're gonna run out of something to say, always remember those things in the back of your head. Come with like a TV show that you've

watched recently or something, a movie you saw, just something that you can talk about or recommend. I have found that the conversation usually flows in some sort of direction. So I wouldn't like rush to change the direction to be to talk about the topic that you prepared. like these aren't like things that you must say or things that you must know about her after the date. You don't have to leave knowing what her middle name is or how many siblings she has. But this is all just things to have in the back of your head.

Cause I know for personally, I get worried that there's going to be an empty space or I'm going to out of things to say. So I like to come knowing that I won't run out. Other good topics to bring up are family, siblings, what they do, where they work, where her friends work. You obviously know this, but I wouldn't bring up like anything that's going to stir the pot. wouldn't bring up this is dumb, but you're not going to do this, but like politics or

anything like controversial, don't bring up Kanye West, like shit like that. You don't need that on a first date. I don't care if he's your favorite artist, she'll find that out later during a karaoke night, but if you guys like each other enough, you'll learn all this shit about each other later. It's not a today thing. So after the date, my advice is to reach out and if it went well, reach out and say, hey, I had a really great time with you tonight. Would love to see you again.

and then maybe in a next message say like, how's 730 next Thursday at your favorite sushi spot. This is also a good time to remember something from the date that you guys talked about. I mentioned also in the ghosting episode that I took that girl to a taco place because she mentioned that she liked tacos. So I think it's a good time to recall that and think about something that you talked about on the first date and bring that back up and go there.

Josh Felgoise (21:36.958)

Maybe during the date you guys talk about something that you want to do for that second date and that's even better. That gives you already a leg up. So bring that back up. But I think when you send this text depends on how well the date went. I've sent this text either if the date ended it, let's say nine 30. I've sent that text at like 11 or I think the next morning is always a good bet. You're not going to go wrong with that. I think you can also send just the first text of

Hey, had a really great time with you, would love to see you again and wait for her response if you're not sure. You don't have to throw in the second option of the date already. Of course, it depends on how you're feeling, your thoughts and feelings after the first date, but just wanted to throw in both options for you to have. I'm also not great at texting in the meantime, like the...

Hey, how's your day? How's work? What'd do? I think it gets like a, gets really bland and repetitive quickly. So I like to, this is another, another reason I like to set the second date and then hold a couple conversations in the meantime, but not have this continuous back and forth that doesn't really have any substance yet. and wait until the second date to get to know her more. Again, that's a personal preference thing. I'm just not great at

the random conversational texting. That's just me. I'm sure some of you relate to me there and I'm sure there's people out there that are really good at it and actually enjoy it. So another personal preference thing. I also tend to read way into texts because you genuinely have no idea what the fuck someone's saying over text and I don't want to have to read into something and think about it or overthink about it. So I like to keep it kind of short and sweet.

And this is if the date went well. If not, I think it's always nice to send a text maybe the next day saying, hey, it was really nice to meet you, but I don't see this going any further and I wish you all the best. I think that's just a nice thing to do. Again, you don't have to do that, but you never know what could come of that in the future. You just never know. Also, I struggle with this myself, but if you can, I really think it's important to stay present and not...

Josh Felgoise (23:57.13)

think so far ahead about the next couple dates or the future with this girl. Again, you just met each other, so don't get so attached that if it ends up not going in your favor that you're not so heartbroken and devastated and that you know you can get back up and try again and go on another date. But if you've gone on a few and they haven't gone well, I think it's okay to take a step back and take some time off and then get back to it. So at least for the first few, I would say

to have the mindset of, if it was a good date, that was a really good date. I'm excited to see where this goes and what the next one's gonna be, but not that she is my future and we're getting married because it was such a good date. I've had really good first dates that haven't, or first and second dates that haven't gone anywhere after that, and that's okay. It's still something I do all the time and I remind myself to take it date by date and see how I'm feeling.

see how we're vibing together. It's also about how you're feeling. It's not when you change the mindset from does she like me to do I also like her? There's a shift there that can really help put everything back into perspective and it's not all about her deciding on you. You have to also like her, which is something I have to remind myself of a lot of time on a first date because I get really heady about whether she likes me or if I'm making a good enough first impression.

So this is a good kind of mental reset for me or for you if you kind of catch feelings easily or if you fall quickly after a couple dates, which I tend to do. This was kind of my comprehensive first date guide. I hope if you're going on a first date tonight, if you're listening to this, if you're going on one soon, I hope it goes well. And at the least you learn something new.

And if you aren't going on any dates soon, I hope this got you excited about the possibility or motivated about the opportunity to go on a few soon and try it out. Because why the fuck not? I know this is always said, but if you don't ask, you're never gonna know. If you don't try, you will not find out. So there is only one way to do it and you will fall on your face sometimes. You will get rejected. It's all part of it. I'm gonna do a whole other episode on rejection.

Josh Felgoise (26:15.667)

because it's something we all face and we do not talk about enough as guys. So yeah, that's, that's going to be a whole other topic. I do want to add in that I have been there and I have been extremely nervous to go on a first date to the point where I think it's just easier or better not to go on it or not ask to go on it. But really like the worst that happens is

you get rejected or she says no and the best that happens is you go on a really good date or you build more confidence in yourself for even trying in the first place and allowing yourself to take that shot because realistically at the end of the day there's so so many more opportunities out there for you and you just have to remember that and be in that positive mindset about it.

After recording this episode, I feel like this episode is the essence of what I was trying to do with this podcast in the first place. This is exactly the type of content I envisioned creating when I thought of this idea a year ago. I wrote down in my notes, first date guide for guys of in May of 2022. And I'm so happy that I feel confident enough to make an episode with

informed advice and hopefully give you a look into my dating experience because that's what we need more as guys in our 20s. That is exactly what I was looking for and couldn't find when I thought of this idea. This is the content I envisioned creating and this is the content that I will continue to make. I plan to and I commit to sharing more of these experiences with you genuinely and

openly and transparently so that you don't feel alone in all of this shit you feel validated, can't think of word, in this experience. We're all going through this alongside each other. We're all going through this together, but we're just not talking about it enough or giving each other enough advice or recommendations for each other. So that is my purpose here.

Josh Felgoise (28:32.467)

That is the point and I think this episode really encompassed that. As dumb as it sounds, I'm really proud of this one. I hope you get some good advice from it. As I said, I plan to continue doing this type of content for the solo episodes. So please send in any topics that you want me to talk about or you're wondering about or just have questions about and I'll talk about it or I'll find the people and have them on as guests that have more informed.

perspectives on these types of topics. If you liked this podcast, I really hope you did. Please give it five stars and leave a review and send any questions, topics, things you want me to talk about or things that just should be talked about to my email, josh at guyset.com, j-o-s-h at guiset.com and I'll be sure to talk about it. Also follow me on Instagram and TikTok at the guyset, T-H-E-G-U-I-S-E-T and check out the website guyset.com, guiset, guyset.

for so much more content. shit sorry I think I forgot to say to leave this podcast five stars and our positive review. Thanks again for listening and I'll see you next Friday. See you guys.