You probably get lots of letters, so I understand if you can’t reply back. But I really will appreciate it if you do.
Anyway, I’ve liked this guy for the past 9 months. I’ve suspected that he kind of likes me too, but I didn’t have any solid evidence. Recently, I found out from one of my best friend that he does like me. It turns out that he told her that he liked me... 5 months ago. Somehow this piece of information slipped her mind until just a week ago.
While I’m silently cursing my friend’s short-term memory, I’m also wondering about what I should do next. You’re probably asking, “What’s the problem? You like him, he likes you.” Well, the thing is that we’re both awkward. Awkward like turtles. We’re acquaintances, but not really good friends. Another thing is that he’ll be graduating in June(he’s a year older than me) and I might never get to see him again. My current situation is an opportunity I don’t want to miss. So... how do I turn our acquaintance status and mutual liking into something more? And what do you suggest I do next?
A slightly awkward turtle that is liked back
I do get lots of letters, Turtle, and if I had several more brains I would respond to all of them. To any Sparklers who submitted unanswered questions way back in the mists of time: I apologize for only having the one brain, and if your questions are still applicable, please go ahead and send them again!
Before I start in on your answer, I want to point out that this right here is why I often recommend against playing telephone with your romantic interests. Heck, your case is as straightforward as they can possibly get—one girl had to say "a boy likes you"—and it took five months. If any additional people had complicated this chain, you wouldn't have found out about this until you were already living with your Moon Husband in your orbital space-house.
Anyway: turtle dating. Here's my advice.
1.) Definitely go for it.
There are always timeline-related reasons not to pursue a given relationship. He graduates at the end of the year, he graduates in two years, college only lasts for four years, the sun explodes in 5.5 billion years. As far as I'm concerned, if your timeline is long enough to allow a a few dates, and you think you'll enjoy them, it's worth pursuing—for the experience itself, and because you never know if your paths will cross in the future.
2.) Don't put him on the spot.
You say you want to turn this acquaintanceship into something more, but I'm not sure if that means you're willing to tackle him in the hallway and create many babies, immediately, or if you want to become better friends before you move on to the dating part. If it's the latter, try to hang out with him in a group setting; having other people there should dilute the awkwardness among the group, so the two of you aren't just constantly walking into each other and apologizing and falling down the stairs.
If you're comfortable with dating him right now, and you just don't know where to begin, the most important thing is proceeding with the caution of a turtle. Do not just stomp up to him and ask him out. To a terribly awkward dude, unexpectedly asking him if he wants to go out, in person, is exactly like kicking down his bedroom door and shouting "Nice underpants, idiot," in that he will just shriek and hide from you, even if he does want to go out, and they are nice underpants. To avoid this kind of pressure, I'd suggest being cutesy or flirty with him in person, to lay the groundwork, and then actually asking him out via text or online. Of course, his response will probably be "gbnml,,,,," because he will have fainted onto his keyboard in disbelief, but it's still better than the alternative. If you can't text him or do this online, leave him a note or something; any approach that means he doesn't have to deliver his answer to the actual face of an alive human girl.
3.) Pick the right venue.
I know I usually say to look for stuff that the two of you have in common, but when you're dealing with Awkwardness McGee, the most important thing isn't common ground—it's finding a setting that alleviates the awkwardness. For example, if you both liked comics, you might think "We both like comics, so we should look at comics together, which cannot go wrong in any way!" Later that day, the two of you will find yourselves standing motionless in Ye Olde Comics Dungeon, which is otherwise deserted, flipping rigidly through comics you grabbed at random because you were nervous. "This comics are... good," you'll say idiotically, trying to break the absolute silence. "Gack," the boy will respond, because he hasn't spoken in forever and his throat is dry. You will realize you're holding an issue of Hawkeye, even though Hawkeye is awful.
My point is that dating is rough enough when only one of you is a bumbling disaster; if you're both awkward, do not start with something secluded, or overly romantic, that only involves the two of you, alone. Do something where you're focusing your attention elsewhere, not necessarily on each other (the movies, a football game) or something that involves activity (bowling, mini golf). Do anything that keeps you occupied, or that gives you a lot to talk about; otherwise you'll find yourself describing your weird dream for two hours, unable to stop yourself, while the boy struggles valiantly not to fall into a coma.