Do you think this could potentially be awkward?

It could be awkward, but it doesn’t have to be. You could try diffusing it with something lighthearted that makes it clear you are adults now and that you no longer have a crush on him. Maybe something like, “Hey, now that we’re not silly 13-year-old kids anymore, want to catch up?”

It was a long time ago. I think it would be fun to catch up. Yes. Do it.

Wow your middle school crush, almost all grown up. I think you’re safe, middle school is over, and everyone moves on. Actually, if you’re beginning college, real life is ahead of you, and not behind you.

If you’re worried about how he’s going to take it, include him in a group of people going to get coffee the first time, and introduce him as having “Two Degrees of Separation” with you.

Sounds exciting. First make sure that you are set on being platonic – if not don’t lie to yourself + set things up to be more awkward + all. You are both older + more mature + the persons you were back then are a farcry from what you are probably now.

I’m getting the feeling that you might find it kind of easy to fall back into a crush on this guy. If you think that could be so, then I would say don’t. Wait and see if he invites you, and if not, let it go.

Oh, wait—what would I do? I would probably ask him, and then regret it and be embarrassed all over again. But you don’t absolutely have to do that.

[Edit] Not everyone abandons old loves! I have known it possible to rekindle a middle-school or high-school flame after 40 years or more. Some seriously romantic types are very susceptible to live reminders of their early heart throbs. After only six years you have hardly even had time to forget him.

Go ahead and ask him. Say something like, “Wow, I was surprised to hear your name. I hadn’t thought of you in years. Want to go for coffee and catch up?”

I would wait for him to approach me this time around. I wouldn’t want him to feel uncomfortable again.

If it were me, I would wait a while and see if he made any move in a friendly direction first. Patience.

Well put, @Judi. Here’s an application of my favorite “reversibility” principle. If you don’t ask him now, you can always do it later; but once you’ve asked him, you can’t unask him.

I would leave it alone. I think the potential of the same thing happening is there.

Drop it. It is amazing how deep those old scars can be, and how they can dredge up at bad moments.
If he asks you out for coffee, the politely say yes.

I wouldn’t be in any hurry to ask him out.Like the others have said,I’d wait.

Chit-chat on the way to or from class. You can get a pretty good idea of whether he has let go of the embarrassments of middle school.

I wouldn’t. What @Jeruba said is how I feel about most things.

I agree with @filmfann . When I was a tweenie, I was in the school library when this boy came up and said “may I help you.” I was just at the age where I was being more outgoing, so said jokingly “nothing can help me.” By this time his friends had walked up, so maybe he just wanted to impress them, but he responded and said “you’re tellin’ me!” I was so embarrassed.

Now fast-forward to Senior year, graduation exercises. This same stupid guy just happened to be paired with me to walk in graduation. We were randomly paired up girl/boy. Anyways, he kept trying to joke with me and strike up a conversation, and I totally froze him out. Payback’s a bitch, dork!

However, unlike @filmfann suggested, I would make him work for another chance.