I'm trying to be original so... if you ever feel dumb, just remember that sometimes sloths grab their own arms thinking they're tree branches and fall to their deaths. Anyway, there's this boy... Ugh. I know. So original. Let's call him Roscoe. Roscoe and I regularly attend religious classes together. He once told me we should get together. And recently, he flirted with me the whole class, winked at me, told another boy to stop flirting with me, and then played with my hair a little bit. I like Roscoe, but I don't know if he even likes me. I know it seems totally obvious that he does! But I'm bad at these things Jono! Do boys just randomly play with girls' hair? Does Roscoe even like me??? And if he does, what do I do after that? And how do I ask for his number in a non-weird but I-like-you manner?
To demonstrate that even I make mistakes, my answer to this question was going to be: "Are you kidding? No boy will randomly play with the hair of a girl he does not like; Roscoe likes you; and you can ask for his number by saying 'So what's your number' the next time he inexplicably plays with your hair." But apparently I was... wrong??
The LW updated with this:
Ahhhh... Jono. I emailed you a while back with a fact about a sloth because I attempted to be original, so here is another fact about sloths. Did you know it takes about 42 hours for sloths to do the HND?
Anyway, here's the problem: there's this boy (yes. original). His name is Roscoe, and I am 99% certain I have emailed you about Roscoe before. I told you that he liked me, played with my hair, etc etc. The whole point is, I have Roscoe's number now... and we talk. But whenever we talk, it's like he can't keep a conversation. Like, we'll be texting and it's like he just doesn't put any effort into a conversation so this is how it plays out:
Me: Just studying! How about you?
Roscoe: Nm rlly
Me: shoot me
And then what am I supposed to say? Roscoe can hold a conversation perfectly well in person, but when it comes to any other form of communication, *poof* not happening. My point is, why are some boys able to hold a conversation in person... but not over a text, phone call, etc.?
Talking to a wall
You know a lot about sloths, TTAW. Let me guess some things about Roscoe: he's like 8/10 attractive, he's personable, and he always seems to have a lot going on socially. Am I in the ballpark?
One of two things could be happening here, and I'm not positive which it is. Either he's sleazy or he's just... dude-y. He's playing you, or he sort of likes you, but is just so laid-back that his interest is kind of flaky. Neither is really a great option, but here are the possibilities as I see them.
Possibility 1: He's Sleazy
The evidence in favor of this one is that he outright told you that you should get together (which is pretty brazen), pursued you aggressively (confronting other guys in the process), and flirted with you physically (hairwise). If he is in fact a sleazeball, one reason for his awful texting would be that sleazy dudes believe that being distant and unavailable while texting makes them more desirable. (I have links to prove this, but I don't want to introduce you to any more pickup artist philosophies than I already have, because these guys are a bunch of gremlins.) Anyway, this is just one option, and hopefully it's not the case.
Possibility 2: He's Just Really Chill
I've known some guys who just could not be bothered to care about stuff. If it was a thing that was happening, they didn't care about it. They wore flip-flops and Patagonia shorts. If they got a text that said "FLEE TO THE NEAREST EMERGENCY SHELTER," they would probably respond "Nm rlly." Evidence in favor of Roscoe just being a really chill dude: you can apparently hold a conversation with him in person without concluding that he's bored by you or sleazy. Also, he hasn't said anything blatantly sexual to you (as far as I know).
I don't think Roscoe's just being cool with his texts as some kind of sleazeball game, because people who do that are always doing it to get in your pants, and from what you've said, your pants don't seem to be on the menu. That leaves the second option: he's not playing an angle, and is just sort of a laid-back guy all around. This is the slightly better option, because it means his interest—such at it is—isn't part of some grand scheme. But do you even want this guy's lazy slacker interest?
I know he acts genuine when you're together in person, but does he seem that way over any other means of communication? You implied that you two have actually talked on the phone; is he just as terrible a conversationalist in that context? I mean, it's hard to imagine a guy going "wat" and "nm lol" through a whole conversation, but was he similarly halfhearted and low-effort the whole time? A guy who's just lazy about texting is one thing, but if he only pays attention to you when you're physically in the room, then it seems like he only cares about your physical girl stuff, and has no interest in your personality (or mind, or life).
It's possible that I'm being too hard on a perfectly nice dude, so how about this: the next time you two are around each other, does he talk to you about anything meaningful, or remember anything you've said about yourself previously? Does he know any important things about you? Does he show any interest in you as an actual person? If he truly is attentive and earnest when you're in the same room, then maybe he's just a strange guy who happens to be a bit lazy, and, dare I say... sloth-like. But if his only commentary is "We should get together" and "You have nice hair," then he's all sound and flirting, signifying nothing.