How To Have a Great First Date

Josh Felgoise (00:00.204)

Welcome to Guy's Set, a guy's guide to what should be talked about. I'm Josh, I'm 24 years old, and I'm here to find all the tips, advice, and recommendations for everything you're wondering about. Let's get into it.

Josh Felgoise (00:17.998)

Hi guys, welcome back to guys that a guy's guide to what should be talked about. Today's episode is a requested. I wouldn't say highly requested, but it's a requested topic by a couple people because I did an episode on this maybe a year ago and I think it's time for a refresher. I think this is a topic that should be probably revisited and redone every six months, every year or so just to come back and give some fresh.

Give a new perspective, give some more advice on. I think it's always a topic that advice is appreciated about and sorry, there's a sock in the middle of where I am. I think advice on this topic is always helpful and never goes out of style. So today's episode is all about first dates and first date advice. And it's just a refresh on first dates in general and how to approach them, what mindset to go into a first date with, what to do, what to say, what to text.

and all that good stuff. So that is what I'll be doing today. By the way, I am in no way a dating expert. I do not claim to be a dating expert and I will continue to not claim that title. Nevertheless, I have gone on a few dates, some good, some bad, some great, some terrible, and I am just here to share my experience.

and advice and what I've learned and what I've learned about myself and the mindset I've improved on in hopes that you can take something from it too and use some of what I've done, some of the mistakes I've made and prepare yourself for your first dates and any upcoming dates with new people. So here we go. Let's get into it. Let's start with the mindset going in to dates or dating. And I think this is probably the most important thing I'll talk about today. And I'll talk about it again at the end, because I really want to hit this part home.

is the mindset you have going into a first date. Now, if you're going into the first date thinking that this is going to be the person you end up with for the rest of your life, I don't think the date is going to go well because you're going to expect so much from that person. You're going to expect everything to be perfect and when there's something that's off or something that you consider to be maybe like a red flag or a beige flag or a yellow, whatever the fuck, whatever color you wanna decide on.

Josh Felgoise (02:30.954)

you will nitpick it and decide that that person is not right because of that little thing. So if you're expecting so much from this person on the date, you're setting yourself up for failure. So don't go into this expecting this to be your end all be all of everything and the woman or whoever you're trying to marry or going to marry and have your babies with. Like do not have that mindset going into your first date.

What I will say that I think works for myself is going into a date looking for a good vibe or going into it looking for good conversation and just a good time with that person. Not expecting the world from them, but expecting them to ask questions and ask you about yourself and to have like good answers and a good conversation and good banter and just be someone you want to spend more time with. That's what I look for. I think that's probably the best thing to look for in a date or when dating.

is that it's somebody you want to spend the next date with. It's that, it's just that. Having the mindset of like, do I want to talk to this person more? Am I really excited to buy them? Like, do I get butterflies when I'm around them? Am I excited to see them again? Like, that's what I look for when I'm going on dates. And that's what I think you should look for too. It's just, do you vibe with that person? Do you want to see them again? Do you like what they ask you? Did they answer your questions and have follow ups and were excited about what you have to say and support what you're doing and like think what you're doing is cool and

people dread the first date because there's so much anxiety and nervousness around a first date and as expected as should be and will be. I don't expect that any first date I go on or you go on will be very different that you're just like so confident one day like confidence definitely comes over time and you get more confident with going on more dates or get confident when you get more confident in yourself. You can build confidence but there's always an element of nervousness or anxiety going into a first date. You don't know the person.

And nowadays, especially because a lot of dates we go on aren't like set up from a friend of like the olden days with our parents, like not olden days, but like 20 ish years ago. Like people don't really set people up anymore. So you don't know that much about this person beside their pictures or what a friend thought of them from college. When you text them like, Hey, did you know this person from college? Like I see the, see that you went, they went to Michigan. Like, do you know them? And he's like, yeah, she was in X sorority. She was nice. Like, yeah, have a good time. Like you don't know.

Josh Felgoise (04:49.686)

anything about this person. so it's normal to be nervous like it that is a very normal response to meeting somebody new for the first time. But if you can go into it with the mindset of I'm not looking for the rest of my life. I'm just looking to have a nice time tonight and have a good conversation and meet somebody new and maybe I want to see them again. Maybe they want to see me again. And I also think the best way to go into it is with the mindset of not judging them or expecting that they're judging you like this isn't an interview. This isn't a job interview. You're not

being judged and at the end of the day, like that's what a date is. If you look at it, like I'm going on a date with this person to decide if I want to date them again. There's not, they're going on the date to decide if they want to see me again. And that in itself is like a very judgmental and weird scenario where you're like, do I like this person? Does she like me? Back and forth, back and forth. But if you cut all that noise and go into it with the mindset of, I just want to see if they are a good vibe for me.

I think that's the best way to do it. So I'll talk more about that at the end, but that's the first thing is the mindset going into it. So part one of the episode is about the ask. So when I ask for a first date, I like to ask for a day and a time. Like I find when you go into the ask without a set plan, it's kind of just like lobbing the ball back and forth and everyone's like, yeah, do whatever. Like, I don't really care. doesn't matter. Like, that's just, but if I think if you're the one asking, I think you should have a set.

plan or an idea of what you want to do. what I would, and I don't always do this. Like I'm not always amazing or perfect. As I'm saying, I'm not an expert. I'm just giving you what my, the best of my, best of my tips are. So here are two examples of how I think you can do this smoothly. So the first one would be like, Hey, we'd love to grab drinks. How's seven 30 on Tuesday at this wine bar. And then they can respond and be like, actually like Thursday, Tuesday doesn't work. Thursday's better, blah, blah. And you can go back and forth, but you already have like one piece of the puzzle solved. Like you already have.

the place you're going. Now you just have to find a day and a time that works. But having one part solved, like relieve some anxiety from the ask. Or the other way I think you could do it is just being like, Hey, would you want to grab drinks sometime this week? Then you can wait for their response or the follow up and then say, how's Thursday at 730. Either way, it doesn't really matter. It's just like up to your preference of, of text, whichever you're more comfortable with. One's like a little bit more forward while the other one's a little more conversational, like

Josh Felgoise (07:07.79)

really up to you what you go with, but I think those are two good examples of how to ask out or how to send that like that first ask. And then the second step is the follow up. So we have the ask and then the follow up. The follow up is I like to send a text that day to earlier that day, like the day you've decided to if it's Tuesday, if it's Thursday, whatever, let's just go with Thursday for the example. So let's say the date is at

730 on Thursday I like to send a text like a few hours before and not like at like six or like five maybe at like two Being like hey like really excited to see you tonight looking forward to it or like hey really looking forward to seeing you tonight or hey excited for the date whichever one again like you prefer whichever you're more comfortable with exclamation mark the one out of smiley face like it's up to you just examples, but I like to give that like buffer period and reminder to like

One, remind her or that person that you're really excited about the date and you are looking forward to it. Two, that you're thinking about the person and three, just to make sure that you actually are still on. No one's going to be like left stranded there alone and stood up. So I think that's it's always a good move to send a text earlier that day being like, just really, hey, like really excited for the date tonight or really excited to see you tonight. OK, then part three is the getting ready.

We are very lucky as guys that we do not have to do like literally jack shit before the date list of things we have to do before a date. Go to the bathroom, maybe take a poop, sit off the poop later. Shower, put on pants and a shirt, cologne, deodorant, maybe brush your teeth. I don't usually before the date I do in the morning and the night, but I'll like use like mouthwash or a stick of gum instead. Maybe I'll brush my teeth too. Floss, make sure there's nothing in your teeth.

And then you're literally out the door. Like it is that simple. Maybe shave wherever you want, personal preference, shave anywhere you prefer. It is literally that easy. Like there is nothing for us to do before a date. And I would say that takes me like 10 to 15 minutes. Like really, like not long at all. Like I've had a date at like 7, this is making me sound bad. But no, what I'm saying is you should get there early, but I'll get there. But I've had a date at like 7.30 and

Josh Felgoise (09:24.878)

I was sitting on the couch with my roommates doing literally nothing. We're all just scrolling our phones. And I was like, oh, I should probably get ready. It's like 7 10. And I was out the door by like 7 15, like there five minutes early still. Like it is that simple and stupidly easy for us. So all this to say is that girls don't have it as easily as us. So you have to be there a little early. Like it is, it's a nice thing to do. It's the gentlemanly thing to do. Be at the date early. If we can do one thing to start off the date right, it would be getting there early.

and making sure you have the table and you're set. And it also gives you a chance to like look at the menu. If you're like an anxious person, you don't know what to order and you're gonna like panic order when the date starts. And you're like, I don't even know what I'm get. I'm gonna get like a fucking cucumber mojito because that's the first thing I saw. And then I panicked. What happened to me one time? I don't even like cucumber mojitos, but I got it. And I was just like, no, she got it. So then I got it. And I was like, what was I doing? Why did I do that? I just panic ordered.

I saw something on the menu, which is like, yes, I will have that. So I don't have to be like, can you come back? And we're like, hmm, actually you first. I'm not ready. And like, have to like scope out the menu. So that gives you a chance to do that. So that's always a good thing. But yes, be, be there early at least five or 10 minutes early. And in my experience and the dates I've gone on, I think the girl has always been late and like texting me like, Hey, like running late, like be there in 10. I still think it makes sense or it's a good thing to be early. So even if you're sitting there waiting for a while, text your friends, do the word or whatever, like

scroll through Instagram, can be go poop at the restaurant. Like, you know, just get all your shit done, but be there early. I think it's a good look. Okay. And this is a sidebar on ordering while I'm already on the topic of ordering. We put a lot of pressure on ourself on ordering, but I really do think you should order what you want. Maybe don't order like a Long Island iced tea, but definitely order like what you want. Like, don't be so worried that the person's going to be like, Oh, he ordered a gin and tonic. Like he must be a psychopath. Like, no, like just order what you're actually going to enjoy. like,

cut out all that anxiety and worry about what it is, just make sure you don't order something that's gonna make you like fart everywhere. Like that's the only thing that don't do. But everything else, just get what you wanna order. Okay, but back to getting ready. So what to wear. And this is just what I wear. So I'll put together some guides and I'll put them in this week's newsletter that's coming out on Thursday and they'll also be on my website, guyset.com. But what I would wear on a date is pants, probably not jeans on a first date, I just feel like pants look better. That's my personal preference.

Josh Felgoise (11:47.66)

I wear what I call a fancy t-shirt. I don't think they actually are that fancy. It's just like a plain t-shirt, something without just like a big fucking design on it. Not that I have that many of those, but just I wear like a plain t-shirt, maybe like a light casual jacket, which are hard to find. I'll also put a guide together of those, of what I like or I go for and have bought before. And then like a belt that matches. And then again, with the word fancy, but like fancy sneakers, like white sneakers or something that just like looks good with the outfit.

And if I'm not wearing that, I'll wear like a button down with like an open button down with like a shirt under it or a button down in general. It depends on the weather. think summertime it's harder to dress for a date because it's so fucking hot outside. So you can take off that jacket and just have the t-shirt on. But like I think it's pretty casual. I don't think you have to look like I don't think you have to overdress so much, but just wear something that you feel comfortable in and that you would be happy like presenting yourself with. if

If somebody saw you in it, you'd like, yeah, they're on a date. Like, it's not just like you're going to the movies or just going to like sit on the couch and jerk off all day.

Josh Felgoise (12:50.637)

Okay, um Just be put together and then we're add some cologne on make sure you're wearing deodorant like make sure you're matching and not clashing if you want to send a friend a picture and be like Hey, like how does this look? That's always a good idea. If you have a sister always a good idea or a girl That's a friend in your life very hard to do but a girl that's a friend is you can send them a picture too me You can send me a picture I'll answer if you want to send DM me a picture of your outfit. I'll be like, yep I like it or I'll yeah, but I'll put together some first date guides of like what to wear shirts

these fancy t-shirts that I call a fancy t-shirt, like light jackets, pants, belts, shoes. I'll put all that together. So you can find all that on guyset.com and on like my, all that stuff. I'll also shave. Like I think it looks, it's a good look to shave. It's a little bit more put together. It looks like you put a little bit more effort into it and your look. As I said, I'll put on some cologne, make sure I'm wearing deodorant, floss, like all that good stuff. Just to make sure, like just so it looks like you gave an effort. I think that's.

The least we can do because we really have not, we don't have that much to put in effort wise. So I put in the bare minimum of shaving teeth and like cologne smell good. Okay. And then part four, the date. Now that you've arrived early, ask questions, make sure you're asking questions that you're not just sitting there saying nothing. Here are some questions that I have that I think you can always use and have in your back pocket. What do you do? Do you like your job? Do you like your boss? What's your favorite food? What's your favorite TV show?

What would you bring on a deserted island? What's your living situation like? Do you like your roommates? Do you like where you live? What's your favorite restaurant you've been to recently? Do you have siblings? Where do they live? Yada, yada, yada. Like you can talk, you can ask so many different questions, but like try and let the conversation go wherever it will go and ask follow up questions about it. Be like, do you like that? Or, like how do you feel about that? Just to continue the conversation. Don't worry or don't try and.

check all the boxes of like, I learned that she had siblings and I learned that she has living parents and I learned that she likes her roommates. I learned blah, blah, blah. Like don't worry about checking off all the boxes. This is a hour and a half to two hour most likely time with this person. So you're not gonna learn everything and anything there is to know about that. But you're just looking for a vibe and you're just looking to see if there's attraction and a good energy between you two and that you wanna go out with them again. Like that is what you're looking for. So.

Josh Felgoise (15:10.338)

The things you're talking about are really just to get to know the person a little bit and to see if there's a vibe there that you want to go out again, not to learn their life story in the two hours. So again, the goal is to see if this is somebody that you see yourself with, somebody that you want to see again, like next week, not the person you're going to marry next week, because literally how the hell could you know that from an hour and a half to two hours with somebody that you did not know two hours ago? We will talk about my favorite term, future tripping in just a second. But before we get there,

It is now time for part five, the after. If it's going really well and you feel like you've exhausted all your time at this place, ask if they want to go walk around somewhere or find another drink spot or go to a different coffee spot or wherever you're at right now. You don't have to do this, but it is an option. So you don't have to like end the date because you're at one spot. But if you're feeling it, why not? And then I always like to offer to walk them back or make sure that they're safely in a cab or Uber before leaving. I don't think you have to call the Uber for them.

But I think you can make sure that like they have an Uber and it's on the way and they're in the car before you've gone your separate ways. I think that's just another like gentlemanly thing to do. And I also think saying like text me back safely is also a nice thing to do. So those are just some quick things that you can do after and just to take any stress off like you don't have to worry about having a first kiss after. Don't worry about if did you hug them correctly like don't take all that anxiety off. If it's going well it will continue to go well and if it's not it will not.

Like it's, it's as simple as that. But I do think those are just like two blanket statement, nice things to do after any date, if it's gone well or if it hasn't, like make sure that they've gotten home safely and they're in the car or the Uber or subway or walked back home or whatever. And then, make sure that they've been back safely. So like a text saying like, Hey, did you get back safe? Or just to make sure you got back safe, like wanted to check in to something like that. I think is really nice. whether it's gone badly or great.

Just a good like dating karma thing, which we will also get to again at the end. It just shows that you're a good guy. And I'm sure if you're listening to this, you are a good guy. So do those two things at the end to continue to prove that about yourself. And then part six is the after after. If it did go well, I would text them the next day asking to set something else up. So what I would say here is like, hey, I had a really great time with you and would love to see you again. Are you free next Tuesday?

Josh Felgoise (17:31.246)

And I don't think you'll have to say like, are you free next Tuesday for a drink and this at this time? think you just, now that you've already done that once, I think it's better to be conversational now and make sure that they respond that are excited about going to see you again before you give an actual finite plan. So I think a text like that is perfect. It doesn't have to be exactly that. That's just like a format for what you can say. The wording doesn't matter. I'm just giving you like a structure to work with, but be yourself in your texts. And the last section is the dating appendix.

A few more things to keep in mind. One, this is not a job interview. Like I said in the beginning, remember not to worry so much if you think they like you. Don't spend half the date thinking, well, if I do this, then they'll think that. The point of this date is to see if you're a good fit, to see if it's a good vibe and you like them. Was the conversation good? Did they ask you questions about yourself? Do you think they cared when you answered? You are just as much

trying to see if you like them as worrying about if they like you. So cut out all that worrying or try to a little bit more and spend more of your mindset on how is the vibe or how is the vibe? Is the conversation flowing or did the conversation flow? Do you think you want to see them again or do you want to see them again? Two, don't future trip, also known as anticipatory anxiety. But I think the term future tripping is much more fun to say.

Future tripping is seeing the forest before the trees, thinking or overthinking so far ahead about what the relationship is before there's even a relationship to begin with. Example, well, what if this doesn't work out? What if this all ends up in shit and we never see each other again? How is this going to work if she's from California and I'm from Philadelphia? One of us will never see our families again and the kids are never gonna see the grandparents. You don't even know her middle name. So why are you thinking about your kids already?

or who's going to be your best man at the wedding. This is probably the best advice I can give you is just to take this one step at a time. Stop worrying about what is going to be or what could be or what will be. Worry about how you're feeling in the moment. Are you happy now? Is she making you happy or is the person you're seeing making you happy? Are you excited to see them? Like those are the biggest questions. Use how you felt on the date and how that person made you feel to determine what you do next, not about all the future potential possibilities of what could happen or what will happen.

Josh Felgoise (19:53.772)

Seriously try to avoid the made-up and impending doom of the non-existing relationship The future will come so like just don't rush it I do this all the time and I find it almost nearly impossible not to do and not to think about the potential future But when you start doing that remind yourself of how you actually felt with that person how they made you feel Are you excited to see them like the questions that I brought up before? Are the questions that you need to remind yourself and bring yourself back to?

when you start future tripping about what could potentially happen or what will be. Remind yourself to come back to the present moments. How did you feel? How do they make you feel? Do you want to text them again? Do you want to see them again? If all the questions that you answered are somewhere along the lines of good and yes, then chances are you do want to see them again and you should. I find that it's not always easy to find people who make you feel that way, so don't push that away and don't self-sabotage by future tripping.

And if the answers to the questions that I just asked of how did you make, how did that person make you feel? How did you feel with them? Like, are you excited to see them again? Do you want to text them again? If those answers are not great and like probably no, then here's what I would do. I would send a brief text saying something along the lines of, Hey, I had a really nice time getting to know you or Hey, I had a really great, right. Hey, I had a really great night with you, but I don't see this. I don't really see this going anywhere. I'm going to say that one more time because I just stumbled over it the whole time. Hey, I had a really great time getting to know you, but I don't see this going anywhere.

or hey, I had a really nice time with you, but I don't really see this going anywhere. I think it's as simple as that. I don't think you need to be like, see so much for you and I know you're gonna do great things in your life and you have so much future ahead of you and you're gonna do amazing things and be an amazing person. Like no, just keep it short and sweet. Like chances are if you are sending them this text, like they don't really care if you think they're a great person and they don't care if you had a really great time with them because you're really probably not gonna see them again. So don't.

like overdo that, but I do think a nice quick text does always go far and adds to my last point of dating karma. So dating karma, what goes around comes around. I'm a big believer in this idea of dating karma and that there is positive dating karma and negative dating karma. And this may sound stupid to you, but it's the way that I, I like this idea because it helped me reframe from the bad thoughts and the bad.

Josh Felgoise (22:11.448)

dates thinking like, that was a waste of time and like, what a waste of time. I shouldn't do that again. Or that person goes to me. So that means I'm a bad person. Like I think, I think when you're going on dates, that type of stuff can really hurt and make you feel really bad about yourself. So this idea has helped me a lot in reframing and going back to that like positive, confident mindset of this idea of dating karma. So the idea that like what goes around comes around.

that how you handled previous dates or situationships or relationships comes back to help or haunt and I believe I will be haunted and helped by both the ways I've acted in both previous relationships and situations and dates I will be haunted and helped by both of those things like I don't think my dating karma is not 100 % I've been shitty and I've also been great and I've been bad and I've also been good like it's a learning experience like you're not you're not always gonna be perfect and it's not always going to be great and you're not always gonna handle every situation perfectly

You're not expected to and I don't think anybody does handle it all perfectly. So, like, you will fuck up here and there, but do the best you can to handle it with, like, respect and by being a good person. An example is having the decency not to ghost is always better than ghosting. Sending that text, I think, will lead better things to come your way than not sending that text. I believe that it's all in the small things and in the little acts. So don't overwhelm yourself with first dates. They're not a test.

You're not being graded on performance. If you don't like them, so what? You put yourself out there and you met someone new. Like it is all a part of it. If they don't like you, so what? Not everybody will and not everybody has to. If it doesn't go well, that doesn't mean they're all going to go terribly. And if it does go well, that doesn't mean they're all going to go well either. I believe this is all about living and learning. And I really do believe that you learn so much about yourself through dating and through your experiences and meeting other people.

and how you handle yourself and the questions you ask and the confidence you can form by doing this and by putting yourself out there and going for it and having the mentality of if you don't try, you'll never know. I believe all of that makes you a better person and you learn a lot about yourself through it. So it's all about living and learning, not about testing and practicing. So if you're going on a first date soon, try to get into this mindset that I'm talking about through this entire episode.

Josh Felgoise (24:34.734)

I hope you use some of these tips and I hope that they are helpful to you and any date you go on. I think they're good for any date, not just first dates, but this is like a first date refresh or a first date guide refresh. And have fun with it. Like, it's supposed to be fun. It's not supposed to be so nerve wracking and anxiety inducing. It will be, it always is and it always will be, but it is supposed to be fun. So try and have some fun with it and go do things you wouldn't do with friends or things you wouldn't do otherwise. And go for it.

Why not? That is the episode. If you have any other questions about this topic specifically, feel free to reach out to me personally. You can reach out to my email. It's josh at guyset.com, J-O-S-H at GUISET. No, that's kind of like a esoteric way to reach out to me. You can DM me at the guyset, T-H-E-G-U-Y-S-E-T, or you can go to my website. It's guyset.com and there'll be a question box. You can just like submit something right there and I will answer it and give you an honest answer about it.

But you can also email me if you want if that's if that's your preferred method of communication. If you like this episode, please give the podcast five stars at the top of the podcast page. Give the podcast a thumbs up. Subscribe. Follow. Leave a review. All that good stuff. You can follow me at the guys at T H E G U Y S E T and then below in the show notes, you can leave your email to subscribe for a newsletter that is coming out this Thursday and send anything you want to talk about and it should be talked about to my email to my DMS.

Thank you so much for listening to Guy Set. I hope this was helpful and I will see you guys next Tuesday. See you guys.