I've only recently discovered your articles, and they honestly make me laugh. XD You're way too awesome.
I have a sort of problem that has not happened yet, but maybe possibly just might. To make a long story short, there's this guy that my slightly older cousin (male) is good friends with. My cousin hangs around my house a lot, and so his friend has come over a few times, and when me and my cousin and some of my friends hang out, his friend comes along, too. The thing is, my cousin is gone now. He left the country. Today, in fact. *wipes away a discreet tear* And the other, more important thing is, yesterday, when me and yeah, my friends and cousin and that friend hung out, right before my cousin's friend left, he asked me to call him when I got back from Korea (where I'm going for the summer). And later on at night, when I texted him, he said to let him know if I wanted to hang out.
That's all great, and I want to hang out with him, but the thing is... he's an introvert, sort of. And we only started talking, like, a few months ago, and that was only like, during hang outs when we had other friends. When/if I hang out with him later this summer, do you have any tips on keeping the conversation non-awkward? He's, no offense intended, a guy that kind of... attracts awkwardness, I guess? I don't know what movies he likes, we're not in the same class so I can't ask him anything about homework, I don't listen to the music he does, and... we don't have too much in common. Any help on how to talk to him and hang out with him without me being too overly cheerfully-clingy or being hugely awkward?
On one hand, I feel deceptive even answering this, because I also "attract awkwardness," though the way I'd phrase it is that I am the Titanic of first date conversations. A pretty girl asks me what I do for a living, and I open my mouth and a foghorn sound comes out and I literally crash into an iceberg.
However, I do theoretically know how to answer this one, even if I'm terrible at actually putting it into practice. I'll give you a game plan here in a moment, but let me preface this all by saying it's totally okay to mention that you're nervous or to try to dispel the awkwardness. In moderation, it even helps. When one person in the conversation is super-awkward, he or she is often thinking, "Oh nooo, this person is all calm and collected, while I have the social skills of a barge!" and that sense of being the resident failure in the conversation makes it worse. It's okay to roll your eyes and mention that first dates or alone-hangouts are hard. Just don't dwell on the point. (Things will never get less awkward if you're constantly going, "Ha ha, this sure is still awkward, oh oops I spilled coffee on you, ha ha I suck forever!")
1.) Ask questions about common ground.
I know you don't have anything obvious in common, and I know I've covered this asking questions thing before, but let me clarify here. "Common ground" can be anything that both of you have any experience with. Let's say the two of you get pizza:
"How's your pizza?" This is okay, but it's pretty likely he'll just say "good" and look down at the table in absolute silence.
"How's your pizza? I think Pizzacello's has the best pizza." This is somewhat better, because you've added a personal opinion to provoke further conversation (I'll come back to this).
"Which is better, pepperoni or mushrooms?" Asking for a direct opinion also works.
"Which is better, pepperoni or uranium?" This doesn't provoke a discussion about common ground, unless he does in fact eat uranium, in which case you are now dealing with an unrelated and much more significant problem.
2.) Now stop asking questions. Stop it.
Only keep the Question Train rolling until he actually seems to get interested in the conversation. You'll know this happens not just because he's talking more and sharing more, but also because of his body language—interested people sit or stand straighter, face you more directly, and fidget less than bored people. If he's holding his slice of pizza in one hand but is so busy talking to you he has clearly forgotten about it, he is totes interested and you have a Genuine Conversation happening (I'm referring to the above pizza situation, and not implying that any random guy on the street will produce a fistful of pizza from out of his pocket to show that he is interested). The point is, once he's into the conversation, tone down the questions. You don't want keep going "tell me the square root of 2, what's the atomic weight of garbanzo beans??" and quash his sudden enthusiasm.
3.) Tell a story.
You want him to start talking about personal things—both because that's what hanging out is about, and also because sharing personal experiences is easier than coming up with the next correct thing to say. To get him to share stuff, you're going to have to share stuff too. Talk about something true, that is at least mildly interesting, that is not too humiliating, and that does not involve politics or religion.
"We used to get this amazing pizza when we went on vacation upstate. Funny story..." This is good, assuming what you share isn't completely boring.
"One time I was at Pizza Hut and had to go to the emergency room and the doctor told me I had butt problems!" Nooo, too soon!
"This pizza is really good! There is no God." Nooo, too incendiary!
4.) Have a plan in case he is even more terrible and awkward than you suspect.
I often say that you should have some sort of conversation strategy in advance. I don't mean that you should literally try to plan out the entire conversation, because then you'll wind up having to force the conversation back to whatever it is you had planned to talk about, and the segue will definitely be awkward. ("Let me interrupt your commentary on the sexiest celebrities by talking about my dad!") I'm just saying that it's smart to have something to say if you tell a cool story and he goes "Mmmrph." and looks down at his plate in total silence. Here are some okay topics to use in case of prolonged awkwardness; here are some to avoid. Pivot to one of the topics on your list if he is so awkward that it constitutes a medical emergency.
Any other tips?