Is it weird/improper to ask an acquaintance out through social media?

So I [m/30] went to high school with this girl [f/30]. I wouldn’t say we were ever personal friends, but we had a few classes together a lot of mutual friends. Always had a big crush on her. One of her best friends is my best friends little sister. We were around each other sporadically for many years following high school, hung out at parties and social events here and there, but really nothing significant. Can’t say we talked much besides those occasions.

Fast forward to a couple years ago, I moved to a new city for school. Took a flight back home for the holidays, thought I saw her getting off the same flight when we landed but missed her by the time I got off the plane. We had always been friends on Facebook/instagram. So when I was waiting to be picked up I did what felt like a weird thing and DM’d her on Instagram and asked if it was her. (I’m aware that it can be pretty weird/creepy to randomly slide into a girls DM’s like that). Anyway she responded and it was her. She was nice about it and it turned out she lived in my new city too. I told her I was new to the city and hadn’t explored much and asked her something dumb like it she could show me around. She said sure and that we could go explore downtown sometime, or something like that. But I was seeing someone at the time and nothing further came from it and didn’t talk to her after that. Anyway, since then I got into a serious relationship which ended a few months ago and I figured I should start dating again.

At this point there is no interaction with her and I other than sometimes liking each others Instagram posts. So I’m considering reaching out on Instagram (since that’s really the only way I have to contact her) and asking her to get a drink or something.

So, would that be a super weird and random thing to do? Or would it be worth it to go for it?

Thanks for your help, and sorry for the novel!

Posted Jul 20, 2019, 4:45 AM UTC

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