The Art of Talking to Strangers
Aug 19, 2025
TRANSCRIPT
This is my new apartment. Welcome, welcome to the new place. I am sitting on the couch that I told you about last week that I was freaking out about that I was not gonna be able to return because if I customized it, which I apparently didn't, but I thought I did because I added this ottoman right here, which I don't think you can see.
If I customize it, I can't return it. And it is literally the itchiest thing I've ever sat on. Like I don't I should be wearing sweatpants right now because I am so like I feel like my legs are to break out into hives. It is so uncomfortable. It is so huge. Like if I sit back all the way, if you're watching on YouTube, by the way, you can now watch all episodes on YouTube. So if you want to do that, you absolutely can. Or you can keep listening, whatever you prefer. It's all up to you. But if I sit back like I am, that's a bad angle that I am laying like flat and
It's so itchy, like it is so itchy. And outside of the apartment, it sounds like the Avengers are coming to save New York. it is, I have heard sirens, I've heard like bangs, bombs, like not bombs, that's a little crazy, but I have heard every sound you can hear. So if you hear all of that in the background, I'm still figuring out the sound. This is the first episode I've ever recorded in here, in this new space. So I, I don't know what this is going to sound like after. If you hear loud noises, sirens,
The Avengers are fixing it outside. I'm doing the best I can in here and I'm sitting on the itchiest couch on planet Earth. So they should be saving me from that. that is to set the scene for you about this week's episode and what the state that I'm in in doing it. So if I'm fidgeting a lot and you hear a lot of shit going on, like that's what's happening. But what I'm going to talk to you about this week is my Uber ride.
from last week, the Uber drive that I took from the hotel to the airport after my work trip last week. And it really stuck with me for a multitude of reasons. And I'm gonna tell you about all of it. And it may sound like another normal Uber ride. I mean, I'm you've had some crazy Uber rides. think we all have. Like we've all had those memorable rides. And this one was seemingly not a memorable ride. And that's why I think it was so memorable to me. I'll get there.
Josh Felgoise (02:40.13)
But I first wanted to talk about the Uber etiquette between guys and girls and how much easier guys have it than girls in terms of thinking about safety on a day to day basis. Like I have, I'm setting the scene. I've never in my life thought about my safety in terms of getting into an Uber. Like I've never thought about that. I've never thought that like, if I get into this Uber, like
this person may take me somewhere that I'm not supposed to be going or like this, like this is a weird situation. I've always thought that Uber is the safest situation because like someone is taking you from A to B and like I don't have to drive a car. This is like the easiest, best thing. I've never thought about the safety of it. And I was with my coworker who's a girl, I guess woman, who's like 32. I probably shouldn't.
be assuming her age, woman, I'm going to say woman, and I was with her and she, sorry about the age thing again, she like was super cautious about checking the Uber because she was the one calling it and she said that she never really takes an Uber if the driver has had less than like 50 rides and I have never thought about the amount of rides the Uber driver has given before me. In fact,
The week before when I was on my way to the airport, I found out that it was my Uber driver's first ever ride and I congratulated him on the new job. was like, congratulations on the new gig, like how's it going so far? I did not think about my safety whatsoever because I just thought like, I just never thought that I would have to. Like I just never think that I have to.
And I thought it was like exciting that he got a new job. was like, I'm your first rider. Like, how have I been? This is so exciting. He's like, get the fuck out of my car. And she thought I was crazy for that story. And I was like, no, like I was that was so exciting. And I was like, well, looking back at it, I guess that is really crazy that I I don't know. Like, I just never, never thought about that. I think that's how shows how much easier guys have it than girls or just that I'm like really stupid when it comes to safety.
Josh Felgoise (04:54.47)
either way, that's neither here nor there. So, she's always cautious to check the Uber driver and the ratings and the reviews and how many rides they've taken. And meanwhile, I'm trying to find the first person to drive Uber so I can congratulate them on a new job. And she orders an Uber XL and the guy has like 31 rides under his belt. So she's kind of debating canceling it, but because we had a
quick turnaround time to get to the airport. She was kind of just like, it's fine, like we'll keep it. And I was like, 30 rides is like pretty good. Like it's better than my guy with the one, like that's pretty good. And she was like, okay, fine. Like we'll take this Uber, it's no big deal. And I don't know, I just thought that's like a total aside from the rest of the story I'm gonna tell. I just thought it was interesting that I don't think about that stuff. And I'm sure a lot of guys listening right now have been like, are probably like, I've never thought about that once in my life. Like my safety when it comes to an Uber.
and that girls have to think about that. So I just thought that was like something interesting to share as part of this whole realization journey. So whatever. So I got in the Uber and I looked at the time to the airport and it was like 55 minutes. It was like a 55 minute ride. And it was one of those like, ugh, like I'm already pretty tired. Like I'm exhausted. I didn't really sleep that well the night before. We got up early to do work stuff. And seeing that extra long ride to the airport, I was just like.
And I get car sick really easily so I couldn't like check my phone or whatever and then the uber driver goes so where are you all from and I was like, Fuck like and you know when you're really tired and the last thing you want to do is converse with the uber driver and like start getting into a conversation with this stranger that you're you've never met before and you're probably never ever gonna know again and you're just like
Please can we not like can you just like turn the radio off and like can I put the window down and like just try and fall asleep? Like I do not want to talk right now So when he was like, so where are you guys from? I was like, Here we go Like can you tell me something that you would rather do than have a conversation of small talk with an uber driver like fuck? That is the last thing I wanted to be doing so my co-worker like very politely responded like I'm from here and then I politely responded like I'm from here
Josh Felgoise (07:10.348)
And then he was like, so where are you guys off to? Like you're going back to home, you're going back going to somewhere else, like where are your flights taking you? And I realized I was like, I was in for it. Like this was not like a one and done question answer session. Like this was going to be a 55 minute conversation. Like we were going to be talking the entire ride. And you know when you can just tell, like when you're either in a car or you're in a conversation and like, it's not going to end anytime soon.
And if it's going to end, it's going to be you ending it. Like if you've ever been at a party and you're in like that moment of small talk with somebody and they keep asking questions and like, you don't want to be rude, but you're also not really interested in the conversation. So you stay for as long as possible and then you either be like, oh, hey, oh, like look over there, like, oh, have to, I have to go to this person. Ooh, like the shrimp look really good. I don't know what there's no shrimp at the parties I'm at, but like, I don't know why I thought of them. Like, ooh, the mini hot dogs look really good or whatever. Oh, I'm going to get another drink. Like, do you want a drink? And then like.
you're trying to get out by saying, you want a drink? And they're like, yeah, I'd love a drink. So they come over to the table with you and you're like, like, fuck, how do I get out of this conversation? So that was me in this Uber. And I realized that this was going to be a 55 minute conversation. This was not going to be a one question wonder. And he was also one of those guys who sounded super high. You know what I mean? Like he was like, what's good, man? Like, yeah, like what's up?
like where you guys off to? Like where are you headed? And to set the scene, was in, I've set the scene a lot, sorry. To continue setting the scene, I was in LA. So like people there are like chiller and like they're by the beach and like the water and like blah. And that was what this guy was. Like he just had that like really chill tone of like dude, like that's super suck. Like that like kind of.
I don't know, like, ugh, don't have the right word for it. It's like that really, blah, intonation, if you know what I mean. And he was really nice, like a very nice guy, but that was just to give you the way he was asking the questions and the way he was following up. Like, that's that's really, child man, like, blah. And I told him that I was headed back to New York and he was like, bro, like I love New York.
Josh Felgoise (09:26.444)
What area? And I was like, like I used to live in these villages. I'm moving to here. And he was like, like what were your cross streets? And I was like, this guy, like this guy knows like we are going to get into it. And I was like, yeah, like I used to live here. And he was like, dude, like I stayed here one time and like was super conversational and nice. And we were just kind of getting into all of it. So like, then I felt the need to kind of continue the conversation, which I guess I didn't have to, but like,
He was being super nice and it was very obvious that like this was going to help pass the time for him. And it turned out it was going to pass time for us as well. So then I said like, how long have you been Uber driving? Like I shot with the classic question that I think everybody asks, like, how long have you been driving Ubers? Like how long have you been doing this? And he tells us that like he owns a farm in Oregon and that he wants to make some extra money and shows us like a red light. shows us like the tomatoes that he's growing and the
how they're going to like a farm stand in Oregon and like he's gonna go back there the tomatoes and the watermelons and like all this stuff we heard a bit of his life story and then he asked another follow-up question he was like what was the best thing and I'm gonna stop doing his accent because I feel like it's either offensive or like I don't know he was like what was the best thing what was the best thing you got no what was the best thing you guys ate while you were in LA and I told him this amazing sushi restaurant that we went to that my friend recommended called Matsuhisa that was so good that we
could not expense because the first trip I took, the first ever work trip I took where the sushi rule now exists at my company that I call it, my previous boss call it, that was because I went out and got sushi and expensed the entire bill to my company. And the person who handles expenses sent that to somebody else and was like, hey, do we cover this? And they were like, no, we do not.
cover this unless he went with like somebody he was supposed to go with like unless he went with like he did this as like a work thing like no it just looks like he went on his own and got sushi which I did and spent a lot of money no we will not cover that like we will cover one fifth of that but good try so we did not expense that but it was really great restaurant and he was like man like you went and like I started to actually like enjoy the conversation with this guy
Josh Felgoise (11:39.702)
And he tells us about his friend who's in Ireland working with Hosier on his new album. And then he asks, like, what's the best concert experience you've ever had? And I was like, that's actually a really good question. Like, I was like, you didn't ask best concert, right? And he's like, no, like the best experience. And I said to him, like, you've got a lot of great questions. And he responded and he goes, I'm interested in people, man. And I was like, wow.
Okay, that's pretty cool. Like he genuinely seemed really interested in like getting to know us even though He was never going to know us again. And this was just gonna be like a one-time Kind of exchange and I thought that answer was so cool Like he was like I'm just interested in people and I was like, wow, okay And I thought about how cool it is to engage in a conversation with somebody
for an extended period of time with no expectations tied to it. Like, we were gonna be in this car for 55 minutes or so and have a conversation that we either never remembered again or never forgot again. And no one was looking to gain anything from this conversation except to get to know somebody that they will never know again. And I
kind of thought about that during this conversation about how cool that is and how genuinely interested this guy seemed in what we were saying and asking follow up questions and trying to get to the root of who we were and what we like and what we don't like and where we've seen in the world and what we like to eat and what we like to do and what drives us and it was this incredible kind of conversation that
Nobody had any expectations for and nobody had anything tied to and in another 40 minutes or so we were going to go our separate ways and most likely never see each other again because we don't know each other's names. We don't have each other's numbers like I'm sure you could find like in the records of Uber and like blah blah blah but like for the sake of story and for the sake of the experience like I'm not going to find this guy again like he's not going to we're not going become friends like.
Josh Felgoise (14:01.986)
He's not being friends with my coworker. We're not going to see each other in our lifetimes again. And I thought how cool it was to just be in the moment with this other person or with these other people and just get to know them and how abnormal that kind of is nowadays. And near the end of the ride, I thought back through all of the questions he asked us throughout the ride because I thought they were such good questions. And I was like, I
wanna remember these for the next time I meet somebody that I wanna get to know more about or just like ask questions to and I think these are good questions for a date, for coworkers, for anybody. Like if you don't know what to ask somebody, I think the questions that this guy asked me and my coworker were so good and memorable. They were surface level enough but they...
they changed the wording enough that they felt a little deeper. Like instead of saying like, what's the best concert you've been to, it's like, what's the best concert experience you've been to. So these are the questions he asked. And like, this was the discussion we had through the Uber drive. He asked, what was the most beautiful place you've ever been? Which got into such an interesting conversation about the places we've traveled to and the places we want to travel to. He asked, what was the most beautiful city we've ever been to?
What was the best concert experience we've ever been to? The best restaurant we ate at while we were there? What you love about the city you live in? What's the best thing you cook and your favorite cuisine? So that's like seven or eight questions that aren't earth shattering, aren't groundbreaking, but they're questions that you can pretty easily follow up with and create an entire conversation and dialogue around with no strings attached.
If you were to go on a first date and ask three of these questions or have three of these questions that like you can always shoot with if there's dead space or dead air or you don't know what to say, I think all of these can lead to more conversation by asking like what's the most beautiful city you've ever been to. You can then ask what what made it so beautiful or what's the best thing you did there or what's the thing you wish you did or who were you with during that time? Are you still friends with that person? Do you still talk to that group that you traveled with?
Josh Felgoise (16:24.84)
What like there's so many more questions you can ask from that. From the question, what do you love about the city you live in? You could also ask what you don't like about the city, what you would change, what area you haven't explored yet, what things you haven't done yet, what things you have done, what's the best thing you've done? Like there's so many follow ups that don't feel like an interview, but more so a conversation, more so to show that you're engaged and excited about what the person is saying and what they're.
thinking about how they're feeling about it and showing that you really care. none of these questions are earth shattering or groundbreaking questions, but they're just good solid questions to start. And they're a really good starting place. And it didn't feel like he had these rehearsed. He wasn't reading them off of a list. Like these were questions that he naturally followed up with or thought about during that ride or from what we said that led to the next and the next. And
by the time the ride was up, the time it was 55 minutes, I was kind of like, I don't really want this conversation to end. And I've never felt that way in an Uber ride before. As I said in the beginning, I was like, fuck, I have to talk to this guy for an hour? I would rather do anything else. I would literally rather do anything else. And by the end of it, I was like, I don't want to leave this car. This is so interesting. This is one of the best conversations I've had in a minute because there was nothing to expect from it. There was nothing to gain from it. And there was nothing to lose, too.
Nobody was overthinking what they said. Nobody was over analyzing or under analyzing. Like it was just there in the moment. And when you continue to engage with the answers, they become really interesting and you get to know somebody through their passions, through their likes, through their dislikes. Like I feel like I know more about this person than I do about some of my coworkers. And like,
I went into this conversation so not wanting to talk to this person and I left feeling like an asshole for having that attitude toward this conversation and toward the opportunity to meet somebody new and learn something about somebody or potentially learn something about myself by answering the questions, by having to come up with my own answers and my own conclusions and thinking about my own experiences because I love talking. Like it's one of my favorite things to do. As you know, I created a whole thing to talk more.
Josh Felgoise (18:47.598)
and I love meeting people and getting to know people and learning more about people, which is why I love interviewing so much. So it was really funny to me that I had that attitude going into it because I was like, this is just the same thing that I love to do in a different format. And it's the same thing that I think a lot of people like to do, but it's in a setting where you don't want to do it, which makes it even more kind of compelling or more interesting to have a conversation because you have to.
In a world where we're so kind of like inundated with virtual conversation, with life in our phones or in our computers, where we're either zooming out for work or slacking or fucking whatever we're doing, like FaceTiming, texting, social media, DMing, all of that, the art of having an in-person conversation with a stranger is kind of fleeting. Like, we don't have to practice it that much if we don't want to.
And it's completely up to us to look for those conversations or seek out those conversations or go out and go out of our way and put ourselves in uncomfortable positions where we would be even in a place to do that. Like take dating, for example. It's so much easier to get on your phone and scroll through an app and say like, there's nothing for me. Like, like dating is so hard. Like the world of dating, dating in the city fucking sucks. Like I'll never find anybody. And
having to go out and put yourself in a position where you're uncomfortable going to a bar, walking up to somebody saying, Hey, I think you're cute. Like, would you like a drink or Hey, like this and blah, blah. Like having to put yourself in a position where it's uncomfortable to go up to somebody is hard because we don't do have to do it all the time. We don't do it all the time. And I'm not saying to go up to every stranger you see and
engage with every person like definitely do not engage with creepy or weird people like that is that is not that is not the point of what I'm saying here but I think one of the points is that to have a anti-social kind of attitude towards an opportunity to meet somebody or toward I think it's important not to be anti-social and not to have that attitude that I had toward an opportunity to meet somebody new or a moment where you can get to know somebody on a deeper level
Josh Felgoise (21:08.84)
even if you may never see that person again, because you don't know what you learn about that person. You don't know what you learn about yourself from that conversation. And I'm also saying that it's not all that deep. Like, not every conversation needs to be something that you end up with creating a relationship with this person forever or having a follow up or creating a friendship or creating whatever. not every conversation
needs to be something that we think about again or even overthink. Like, maybe you didn't actually say anything that weird to the person and maybe that person isn't actually thinking, wow, what a weird thing they just said to me. Or they are. But maybe it's okay to leave that alone and leave that conversation the way it was. You know what I think is really interesting about that whole conversation and getting to come on here to reflect about
that moment or those 55 minutes of moments with you is that it's similar to a networking event I went to recently where I was put in an uncomfortable position and I didn't really know who to go up to to talk to or who to engage with. And I'm going to something like that again tonight where I don't know anybody but it's one of those things or opportunities that I think I shouldn't pass up on because I'm nervous about it or because I'm anxious about it. And I think this is
really similar to that whole experience. Like, I was in a place or in a moment where I didn't really want to do this because I was either uncomfortable about it or just didn't want to have to engage or wasn't in the mood to engage. And by the end of it, I felt like a dick for having all of those feelings. And that was the same for that networking event. Like, by the end of it, I felt like how could I not have gone to this? Like, I learned so much about
that me from that experience about having to put myself in a position where I wasn't in a comfortable place that I'm usually always in by having to engage people I don't know. And maybe those didn't turn out to be the opportunities I thought they would be. Maybe I was rejected by something that I wanted to do, or maybe I landed on my head instead of on my feet in a couple of those moments and I said the wrong thing or just like tripped over my words like I have right now.
Josh Felgoise (23:34.402)
But that's all okay. Like, I put myself in a place that I wasn't used to, and through that I learned that I'm okay in that place. Like, I can handle myself in those moments. And even though I overthought some of those moments after, that's okay, because I survived that time. Like, I didn't die, I didn't pass out, like nothing bad happened.
Maybe there were some interactions that I wish I had said things differently or done things differently or followed up differently and actually even followed up with some of those people that I didn't. But those are all learning experiences and those are all moments to learn from and gain something from. And I think if you stay in the comfortable place and stay in the times where you feel like it's easy or feel like it's comfortable,
You just don't learn a lot about yourself and you don't give yourself the opportunity to learn more about you. And at the end of the ride, when he got out to get our bags from the trunk and we got out and started getting situated, he said, I really enjoyed, I really enjoyed, no, I'm not do it. I'm not gonna do it this way, I'm sorry. I really enjoyed meeting you guys and hearing your stories. Thank you for talking to me and thanks for getting to know me. And I was like, like that is such a nice thing to say.
who knows the impact that I just had on this person by engaging in a conversation. Like maybe right before that he was giving a ride where he said to the person like, hey, like, where are you off to? Like, where are you traveling to? And they were like, you know what? I'd really rather not talk right now. Like, I don't. Or maybe he was having a bad day or maybe like you just never know what impact you have on somebody by having a conversation, by getting to know them. And it was pretty apparent at the end of it that
our conversation had an impact and he thanked us for it. And I was like, I've never been thanked for a conversation before. Like I've never had somebody say, thank you for talking to me or thank you for getting to know me. And I really enjoyed hearing your stories and getting to know you. And I was like, that was so fucking cool. And he asked for our names one more time and extended his hand for a handshake. And then he said, see you down the line. And I was like, whoa.
Josh Felgoise (25:52.622)
What? See you down the line. Like what does that mean? Like maybe this guy was high the whole time. See you down the line. I was like, wow, yeah. Like that kind of meant that we will never cross paths in our lives again. Like I will most likely never see this person again. See you down the line. Like there was nothing more to this conversation. Nothing less than a 50 minute.
conversation, 50 minute, get to know you, get to know me, get to know like, there was nothing more to it. Just like, that was it. And I was like, Whoa, like, is this person real? Like, it almost felt like he was a figment of my imagination or like a storybook character or somebody sent down to teach you a lesson when you most need it. Like, Whoa, like, I will most likely never see that guy again. And I don't even know his name.
but he left an impression on me and maybe I or we left an impression on him too. And it kind of felt like a lesson or a reminder of kindness and a reminder of a conversation with nothing to gain from it and nothing attached to it. And how kind of cool it can be to just be in a stranger's company and hear their stories and get a little bit of a glimpse into their life. And I just thought this was such a neat
a neat interaction and a reminder that I wanted to share with you, was a reminder that I was given that our worlds can be so small, but the world is so big. And there are so many stories to hear and so many people to meet and so many experiences to be had. And you just never know what impression or mark you're going to leave on someone. And even the people
who you interact with once and never see again. You just never know if what you say will have an impact on them or leave a legacy. And this was a reminder to me that what you do in the small moments and in the moments that seemingly don't count can sometimes matter the most. And to that Uber driver, I'll see you down the line.
Josh Felgoise (28:15.394)
to do his voice. And it sounded like a terrible Matthew McConaughey impression. And to that Uber driver, I'll see you down the line. That is the episode. Thank you so much for listening to Guy's Guide to What Should Be Talked About. I'm Josh. I'm 25 years old and I'm here every single week, every single Tuesday to talk about what should be talked about for guys in their 20s. If you liked this episode, I really hope you did. Please like, subscribe to this podcast. Five stars on the movie. That's one, two, three, four, five stars, not four, three, two, five stars. really, really appreciate that.
If you think we're about that should be talked about for guys to 20s head to my email to my DMs or to my website it's at the guys set thg guisct on Instagram tick tock on also to media platforms at guys set on YouTube you can send me an email at josh at guys.com josh at guisct.com or head over my website guys.com guisct.com and I will be sure to talk about it. Thank you so much. Listen to guys said a guy's guide to what should be talked about and I will see you guys next Tuesday. See you guys.





