Hi. You're a really awkward guy,
(I started to take offense at this, but I'm probably not going to make it to the end of the day without accidentally swallowing my keys or getting chased out of the house by a bat, so I'm just going to let it slide.)
so I was wondering if you could help me with another really awkward guy, who I maybe sort of like. I'm almost positive he's into me. Whenever we're in the same general vicinity he looks at me way more than necessary, and we're conversing with other people involved, he addresses all of his comments and responses to me, even when he's talking to someone else. Also, he smiles a lot around me. But, like I said, he's really awkward. He's kind of really shy (in general, not just with me), and I pretty sure that if I wait for him to make any kind of move on me, we will both be in nursing homes before we have an actual conversation just with each other.
I'm almost as shy as he is, and we have no shared activities/classes/friends, mostly because he's not in my grade. So, short of walking up to him and saying, "So, I noticed you've been creeping on me for a year and half," and assuming I'll get absolutely no help from him, how do I, y'know, make this happen? Or least get us into a situation where I can see if I want to make this happen?
This is a tough one, because you've managed to exclude almost every approach I would normally suggest. If you have no activities, classes, or friends in common, I'm having trouble imagining how you guys met in the first place, and I am forced to conclude that he simply materialized out of the mists one day and started gawking at you like an awkward Dracula. I can work with that, but it's not going to be easy.
1.) The pretext
You can tell how much we all hate finding a pretext from how often movies and books circumvent it. Fictional characters rarely need a pretext; a beautiful contessa gets rescued from pirates by a dashing swashbuckler, and then an octopus steals her underpants, and there you go. Or a sexy female spy has a gunfight with her antihero rival atop the Hoover Dam, until an explosion strategically removes their clothes and they have no choice but to make out. Of course, in real life, spies work in cubicles, pirates die of scurvy, and people rarely wind up in relationships unless they're both willing to trudge through the awkward beginning parts.
So the first step is coming up with a "reason" to talk to him, and I put "reason" in quotes because it doesn't have to be a remotely good one, and in fact it almost works better if it isn't. If you ask for help studying for your AP History test, and you are obviously a history genius, he will realize this is all just an excuse to spend time around each other. "Oh boy, history is so hard, and it's good that you're here to help me," you will keep saying even though you know everything, pointedly rolling your eyes over and over until he kisses you to make you stop. Conversely, if the AP History test is tomorrow and you're like "OH MY GOD, WHAT IS A PRESIDENT??" he might conclude that this is a genuine request for help.
Now, I know you don't have classes together, but I'm assuming that he's previously had classes that you're in now, or that he just has broad knowledge about calculus, or that there is some possible human way to make this work. If that's not the case, then you can try becoming interested in his activities. Ideally his activities would involve Sexy Argentinian Tango, and you could ask him to teach you, and everything would become romantic by default. It's far more likely you'll find yourself listening patiently as he's like "Now, the thing about Orkz is, you see," while your brain struggles not to die. But it's still an excuse to talk about something.
2.) The venue
If you're so nervous that your pickup attempt will result in you going "Please tell me more about blehhh" and barfing, and he's so nervous that his response would be "Well the thing about that is blehhh" and also barfing, then there's no need to do this in person. Extend your lame pretext into a safer venue by asking him to get back to you via text, or Facebook, or e-mail. Soon your inbox will be full of messages about how great orkz are, and then, over time, messages about how you are even better than orkz (which actually doesn't seem like much of an accomplishment, given my limited understanding of orkz).
3.) Making a move (eventually)
If you're studying together, this is as simple as moving your hand to his knee (assuming you're both sitting down; otherwise you will find this maneuver extremely unhelpful). If you're talking online, it's all about being increasingly clear that you do not actually care about history or orkz, and that you are trying to see where this relationship can go. Someone eventually has to suggest moving these interactions into a real-life context, e.g. studying at Starbucks or learning Warhammer mechanics in a comic book store that smells like a foot (hopefully after your online conversations have made you both comfortable enough to keep the nervous barfing to a minimum).
Of course, you can skip every one of these steps by simply walking up to him and saying "Hey, what if we kissed each other's mouths."
What do you think LW should do?