Is there a good way to ask her on a second date when our last date was 5 years ago?

I went on one date with “R” 5 years ago. Afterwards, we exchanged a couple messages, but then dropped out of contact. The last message was sent by her, asking if she had left something at my apartment. I didn’t respond. Dumb move!

I found this all a bit surprising, since we seemed to have a good time. No, not just a good time: the whole evening had a special “charge” to it. In fact, I’ve never forgotten it. Oh, and we made out for a long time.

In retrospect, I feel like I was an idiot not to stay in touch and ask for a second date. I don’t know if things would have gone anywhere or not, but I should have given it a chance.

Now, we’ve both moved out of the town where we met. Fortunately, we both moved to the same town!

Unfortunately, the only way I know of to get in touch with her is LinkedIn, which isn’t the greatest medium for communication. (She doesn’t seem to have a Facebook profile. The only email address I have is her university one, but she graduated years ago.)

We are not currently “connected” on LinkedIn, so the obvious thing for me to do would be send her a request to make a connection, then explain myself in the little message that gets sent along with the friend request. For those who don’t know, LinkedIn doesn’t allow you to freely message someone if you’re not friends with them. That means, if she brushes off my request, I could be left with no way to reach her! So I’d better make the first message good (if I’m going to send it).

So, how should I broach this? It’s possibly she’s entirely forgotten me, so I’d have to start out: “Hi, R. Remember me, Jaltcoh? We went on one date in 2006,” blah blah blah. But is there any way to address the fact that it’s been a ridiculously long time since we’ve communicated? Should I apologize for dropping out of touch and say I realized I was an idiot? Or should I play it cool? Is there any way to defuse the incredible awkwardness of the situation?