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

Asked by Jaltcoh (281

) March 30th, 2011

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?

date reconnect

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13 Answers

Send her a linked in request, but no message. If she accepts, then you can write her a thank you, wondering how you are type way, but DON’T ask her out. If she writes back, you can ask her to lunch or coffee; that’s when you can talk to her about not following through last time.

You can’t assume that you can just insert yourself back in her life. She may be married, she might be engaged, she might have a child, she could have been married and divorced. A lot can happen in five years.

zenvelo (39430

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You sound like a smart person. You know the most about your situation. I would contact her but do it in the way that feels right to you. I’m sure you will not get stabbed.

math_nerd (1871

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Did you ever find what she left at your apartment?

I agree that you just send the request, with the default standard LinkedIn message, and do nothing more until she’s accepted it.

Would it help to think of your next invitation as a second first date?—clean slate? Perhaps she’d like to think of it that way, too, rather than having to face awkward explanations and lame excuses.

Jeruba (55831

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Well, I have to say something in the message… She won’t necessarily know it’s me otherwise.

Jeruba, no, she must have lost it somewhere else.

Jaltcoh (281

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If your name hasn’t changed, take your chances.

Jeruba (55831

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If you remember her she remembers you but figured you blew her off which unfortunately is typical for men now if you want this contact you have to make that contact which I would suggest be the blanket one and let her decide if it’s just too late and that ship has sailed or not.

creative1 (12066

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If she brushes off your request,chances are she remembers you very well. ;)

lucillelucillelucille (34325

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It’s worth noting that her name is very uncommon, while mine is very common. If John Smith recognizes Olga Redenbacher by name, it doesn’t follow that Olga will remember John Smith.

Jaltcoh (281

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The “I think I left something at your apartment” was a suggestion to invite her back over. You blew it that time. If you get a second chance, don’t let it happen again.

missingbite (7531

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I know, you’re right.

Jaltcoh (281

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Thanks, everyone. I sent the message.

Jaltcoh (281

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