Chance encounter with an OkCupid user and some needed advice

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Recently I attended the open house for one of the stops on the Second Avenue Subway, which recently opened and it's quite big news. I ran into one of my casual buddies who was with two girls. I made a lousy introduction, chatted for a bit, and we all went our merry ways.

When I got back home I saw a Facebook post with the two ladies in it. Snooping around Facebook for a few minutes and some familiar photos came up. Turns out one of the two girls (I should add these two girls are sisters) I know from a dating site! And to add to the deja vu, I had messaged this girl back in 2015, never got a reply (and it was lame to begin with). I later chatted with my buddy about it at a New Year's party, and we had a good laugh as he knew the entire story and confirmed a few things with me (yes, it was her, she had met a boyfriend on the site, it was one of his friends, etc).

Well, she's now back on the site so I'm wondering if this relationship went sour. Here's my question: how should I approach this? What should I do? Try to see if I can get set up on a date or something? Or just forget it. I don't feel comfortable re-messaging this girl. Turns out this girl is on the dating site as often as I am.

*I'm almost ashamed to discuss this on here because there's plenty of Aspie railfans in the NY area, and they might know a tiny bit of the back story.

So no one has any words of advice....

It just doesn't feel good to be like "Hey there, how are you? I am the guy from the party and you also ghosted me a couple of years ago!".

Yeah. I know. That being said, I do have a mutual friend, and as for my chances, well, I know they suck. And it wasn't a party, it was a community open house for a new subway stop.

What does your friend say about it? Did he give any advices?

I was uncomfortable at that point delving further. It's a new friendship on that end too...

Here's what I'd do:

Message her on the dating site. Just say something simple like "Hey! I recognized you from the train station grand opening & thought I'd message to see if you might like to meet for coffee/pizza/whatever by the station sometime. What do you think?"

If she responds favourably, great. If not, or if she doesn't respond at all, oh well.. you haven't lost anything and you've gained the knowledge that she's not interested.

She may or may not even remember the message from 2015. Who cares?

She may have recognized you if you have a profile pic up.. and maybe she's not interested, but again, who cares? Nothing ventured, nothing gained. Send her a short message, without reminding her of the past, and see if she replies.

No, stop it, just forget it - don't give someone who ghosted you that much importance, don't show her that you remember her.

If you insist, just send her an intro message, forget about the encounter and the old message- pretend that you have seen her profile the first time ....and don't mention the party encounter, that would make you look like a creepy stalker.

And in case she remembers you be like "O really? I don't recall you at all".

Keep your dignity, you are a man, not a lapdog.

Are you sure? That way she will probably see that he messaged her before.

I'm sure.

So what if she does?

Still no loss. No big deal if she ignores it.. at least he won't wonder if she'll ignore it or not, then he'll know.

Besides, she may have deleted messages over a year old and may not have the memory that he does - it might be like receiving a brand new message to her.

Either way, I'd send the message and see if she responds. Otherwise all he'd do is just sit there and drive himself nuts wondering whether she'd reply or not and there's zero value to that. At least inquiring will give him an answer.. even if ghosting is the answer, it's still an answer and some closure on the situation.

Then she will think that after 2 years of being ghosted he still remembered her and now thinks and he has a chance for some reason. She'll basically think find him a cute loser or maybe just creepy.

Even if she has deleted her messages she will think "Oh, the guy from the open-house has somehow found my dating profile and is sending messages to me, what a stalker!".

I think the best way is to stay away from dating sites if possible. He could know her through her friend maybe or add her on FB if they have that mutual friend perhaps. Idk.

No, but I'm not an eternal pessimist either.

That's probably the way things will go in this case. It is what it is. I'm not going to actively go after her, but if the chance is presented before me, that's when I'll make the move. Dating sites are great if you have no friends in common, but if you have friends in common, skip the dating sites.

Long story short: if I talk to this girl again, it will not be via the dating site.

If these women get 100+ messages, they probably won't even remember you. I'd take the advice where you just pretend like you didn't remember her either and begin anew.

I would, except for one big thing: I've met in her in person. A little awkward to message someone on a dating site when you can somewhat recognize someone by face.

You took the right approach for that.