Conversation and other failures

One summer when I was in college, I worked at a an arts camp, helping out with the dance department. Since I was 19 and extremely single, I was 30% excited about the job itself and 70% excited about the possibility of meeting boys.

Almost right away, I met one. His name was Sean and he was from Oklahoma. We met during dinner at the mess hall. After dinner, he invited me to go on a walk with him. He was muscular and friendly. Score!

Sean and I took a leisurely walk through the woods. We stopped at a building with a dank old piano and banged the keys for a while, laughing. He asked me a lot of questions and I answered them dutifully and flirtatiously. We were off to a great start. He invited me to go parasailing with him sometime on our day off.

Then, on our walk back to main camp, he asked, “Do you ever go into [the city closest to our camp]?” and I said “Not very often,” brightly and cheerily, so enthralled by this nice guy who had taken such an interest in me.

And then he said, “You know, you’re really hard to talk to,” and said his goodbyes, and walked on ahead of me alone.

Was that guy a total dick? Yes, definitely. Also kind of rude of him to leave me to walk back by myself, like he couldn’t stand another five minutes in my so-hard-to-talk-to presence. That said, he had a point that I think about from time to time.

If we don’t know each other very well, I am hard to talk to. I’ll answer your questions, and I’ll be unfailingly nice, but I probably won’t ask you any questions of my own. I am extraordinarily good at leaving you hanging. I will make you do all the work of coming up with things to talk about. I will be so wrapped up in silent panic about what you think of me that I’ll probably miss a lot of whatever connection we’re supposed to be having.


Socially, I’ve always been saddled with this mental cocktail of one part worrying about what people think of me, two parts fear of saying the wrong thing, and a dash or two of boredom with small talk. When I was younger, though, it wasn’t as big of a deal. No one really expects you to make small talk as a kid, and even when you do it, you don’t have to put in much effort. Adults will say things like, “What are you learning in school? What do you want to be when you grow up? What are your hobbies?” And sometimes those are annoying questions, but all you have to do is come up with an answer. There’s not much back-and-forth required, because it would seem weird if you, as a thirteen-year-old brat, showed meaningful interest in your mom’s friend’s job, or what your dad’s golf buddy likes to plant in his garden each spring. You are allowed, within reason, to respond politely to their questions and then fuck off to whatever you were doing before.

Now I’m well into adulthood, so I should have figured out how this all works a long time ago, but I haven’t. I don’t know what to say to almost-friends. In a way, strangers are easier. What do you say to strangers? “Hi. Nice to meet you. How do you know [Mutual Friend]? I like your earrings.” Then you make a show of going to talk to someone else, or get yourself a drink, and you have successfully interacted with another human, with a minimum of awkwardness and a maximum of seeming normal and friendly.

With acquaintances, it’s so much harder: “So. How’s work? Mmmhmm.” The follow-up is an enormous canvas of undeveloped questions. This is where Sean, the terrible boy at summer camp, got frustrated with me. He asked me question after question, and I blithely saw it only as genuine interest on his part–not attempt after attempt to keep the chatter flowing between us.

It’s trendy right now to be introverted and disdainful of small talk, but I mostly hate it because it’s so hard, not because I don’t see its value. It feels to me less like a way to connect with and get closer to someone, and more like a huge opportunity to hurt someone’s feelings with an insensitive question or remark. In the last few years, I’ve read complaint after complaint about the question “What do you do?”, long considered one of the safer things to say to someone you’ve just met. I get why people hate it–it makes those with jobs they hate feel like their identity is being reduced down to that dumb thing they have to do for money. I hate it too, sometimes, because it doesn’t tell the person who I really am. But it used to be my fallback, and now I’ve filed it away as an “only ask if they ask first” question.

The other day I went to a party. It was with almost all people I knew, who I’m fairly sure like me and have enjoyed my company before. It should have been a lovely time, and instead, I was overcome almost instantly with anxiety about what I was supposed to be doing there, what these people thought of me, and what I could possibly say to them. I sat there, watching a dozen or so people talk and laugh around me, and I wanted to sink into the ground and go away forever. I checked my phone for no reason. I paid close attention to when the two people I knew best left for the bathroom, sort of holding my breath until they came back.

The thing is, I remember being young and shy and, for some reason, fixating on age 16 as the point when I would figure it out. I wouldn’t be shy anymore by then! Sixteen came and went, and I focused on 20. Now I’m 28 and only fully realizing that I might actually have to do the work to make this happen.

Being a conversationalist isn’t coming to me naturally. It just isn’t. And that’s fine–it just means I have to practice.

This is where I’m going to ask for help.

What do you guys SAY to people? Moreover, how do you do it without hurting anyone’s feelings? Because one time JD and I were talking with a friend of his who had recently been laid off. And she used to work like 11-12 hour days. And so I said, “What are you doing with your free time?” Which, I realize now, was a bad question. And she responded accordingly, like “Well, I don’t really have that much FREE TIME, I’m very busy,” and I get it, she may have been partially defensive and also actually busy trying to get her life in order–but I felt so bad, and I barely talked the rest of the night, berating myself for being so insensitive.

How do you do it? How do you interact with people you don’t know super well in a way that’s safe and comfortable for everyone?


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