How can I befriend someone I've never spoken to for the whole of our high school life without coming off as a creep?

[Anonymous]

For a little bit of backstory, we’ve always had a lot of brief encounters during high school. We’ve greeted each other, but never bothered conversing, let alone having a deep conversation. Not because we didn’t get along, but mainly because we at least weren’t interested in getting to know each other. One day, I performed on piano in my high school, and she went to add me on Facebook and Snapchat. Despite that, we still never bothered messaging each other via social media.

I’ve snapchatted her in the past with no response. However, one day, she replied to my Snapchat (the first time she’s responded, two years after we graduated high school). From the conversation we had, I discovered she had a bit in common with me. And craziest of all, she’s a five minute walk from my house (she doesn’t know I know this haha). From that moment she replied to me, I wanted to get to know her more, and don’t want the communication between us to die away. Except, it’s difficult finding things to talk about to her, due to the fact that we’ve never really spoken to each other, meaning I don’t know anything about her, regarding what she likes and all.

My worry is that I may come off as a creep. She’ll probably be thinking why after all these years does he choose to approach me? It’s also more awkward, as were opposite genders and she doesn’t have a terribly good impression of me.

I should also add that she's got a boyfriend since last year. My question is because of the past and now having a boyfriend, would it be wise to leave it as is and not bother befriending her? Or should I try? And if I should try becoming friends, how can I do it in a way that’s natural and not creepy. Your advice will be greatly appreciated.

Updates

+1 y

Thanks for the great responses everyone!! I messaged her and got a really positive response!! Now I just have to gradually get to know her, which may be a bit difficult

[bente2]

Tbh I would message her and try to get a convo going. Just tell her you kinda regret not talking to her more in high school and are really curious to see what she’s up to. See how she responds to this, and try to keep it very friendly and not flirty. If you know a little about her eventually she’ll maybe snap you and you can respond to everyday stuff. And then you can try asking if she wants to hang out or smth. I recommend going to play soccer/basketball or see a game if you’re into sports, or just hang out at home. Those are generally perceived as friendly stuff and not nessacerily relationship-y.

[Obtuse]

Just be like a normal human being, you know. Ask her how it's going or at least pretend like this isn't weird, or else you will be weird. I mean if you second-guess these things too much you will come off as a creep with weird body language and an obvious sort of self-doubt which comes off like a weirdo. Just do that shit. Don't ask, not even yourself, just do. And if it backfires no prob. Being able to shrug these things off is also part of not coming off like a creep.

[Obtuse]

Man see what he wants and he goes for it. If he's second-guessing all the time he hesitates... looks at her... hesitates some more, sorta approaches her, turns back, looks at her some more, second-guesses himself, approach, talk all nervously... and not that gives off a super creepy vibe. You have to really think this is no big deal. It's not a big deal.

[Obtuse]

* and now

[Laozi]

It's completely normal. If you both wants to talk with each other then where's the problem. Just go for it. Make daily small talks. Find something that is common between you. And let that be your conversation topic. Don't feel down if she has boyfriend. Just go with the flow.

[Anonymous]

It's another reminder of what I've always hated but at the same time I know will never go away

[Avicenna]

Just focus on making the convo interesting to her