Should I ask out a crush I had back in my highschool years?

I've been single for over a year now after a 5 year relationship. I decided to spend some time for myself then and as of now I think I'm ready to start dating again. I remembered I had a tiny crush on a cute girl who was my schoolmate back in highschool freshmen year (like 8-ish years ago) but, of course, I wasn't really well recognized in school. We never talked, I don't even think we ever made eye contact at all, I think we had no form of interaction whatsoever. But she was cute and a constant honor student so hey, a crush is a crush. We're friends in Facebook and she seems to be doing very well after all these years.

Never really talked to her back then cause:

I was in introverted wuss.

She had a boyfriend.

Should I ask her out? I'm getting a feeling that it would be completely weird that it took me nearly a decade to initiate FIRST contact with someone and this is with the high chance she never knew I went to the same school as her.

Or should I just go out and meet new people?

Message her first if you're not on regular speaking terms and see how she responds. She may be seeing someone now and you're not aware of it. Some people don't publicize that they're in a relationship or have a significant other on their social media accounts. She may even be married, for all you know.

Since you're interested, see how it goes with her.

Personally, going backwards in time (for romance) is not a thing I would do - zero interest in the past.

Honestly I think you should just try to meet some new people. It’ll probably seem a bit weird to her that you’re coming out of nowhere as someone she hasn’t seen or heard from since high school. I mean we all have Facebook friends that we barely even remember we’re connected to. I just think it might come across as odd. Just my opinion though. I guess you don’t necessarily have anything to lose either.

When you're not happy in your present, it's common for certain people to start looking to their past to achieve that. How are you friends on Facebook? Did you make the request, or did she? Is it a Facebook group for your graduating class? I know my graduating class has a Facebook page and people announce activities that the alumni can get together for. Do you two live in the same town? Does she ever like your photos? Maybe start by commenting on a few of her photos and see what reaction you get.

You could then try private messaging her. Depending on the feedback, you could ask her to a homecoming game or for coffee. If the attempt fails, it's not like you ever have to see her again and you could hide or delete her as a FB friend. Good luck.

I like Andrinas approach. I say go for it but do it slowly. Don’t go rushing in there guns a’blazing!

Do you know if she’s single?

If so, hey what have you got to lose :)

And just remember, she should be just as lucky to date you as you are her....if you know what I mean*

Carus*

Personally, going backwards in time (for romance) is not a thing I would do - zero interest in the past.

This is exactly what my friend told me too. I'm curious tho, why is that? I understand that perspective in terms of exes, the people you've been with romantically, but I've never even really interacted with this girl at all. That's why I'm reluctant to message her, even with a little "Hi"cause it seems so out of place since that would be my first ever message to her and it's coming from a guy who went to the same school as her YEARS ago..

Right? All those years of complete silence then all of a sudden a guy you went to high school with messages you a "Hi"? It seems so out of place. Thanks for your opinion!

Does she ever like your photos? Maybe start by commenting on a few of her photos and see what reaction you get.

As I recall she hasn't liked anything that I've posted, though I don't really post much. And as for commenting on a few of her photos, this is where the 'we met in high school' awkwardness comes to play. We're not close, like at all. I am 100% sure we've never communicated at all. So for me to just swoop in and start commenting and showing engagement now? It just seems so weird on both ends..

I like Andrinas approach. I say go for it but do it slowly. Don’t go rushing in there guns a’blazing!

Yeah, that advice made me think harder about how I'd approach the situation. What makes be hesitant is that although we don't know each other, we already have history (albeit a worthless one: we went to high school together but that's it). But that tiny detail makes everything little bit odd and weird..

Yes. Move forward not backward. It would be kind of creepy to just ask her out out of the blue when you never even spoke to her.

Or should I just go out and meet new people?

Nope. unless you are in touch (you are on a committe together, she is in your life currently at least on the edges of it), i would not contact her. If you see her off and on, i might ask her out, but do not suddenly reappear. I tried to do that after i graduated with a guy i had crushed on and i ran into him "by coincidence" but i actually figured out where he would be and it did not go well. Move on.

This is exactly what my friend told me too. I'm curious tho, why is that? I understand that perspective in terms of exes, the people you've been with romantically, but I've never even really interacted with this girl at all. That's why I'm reluctant to message her, even with a little "Hi"cause it seems so out of place since that would be my first ever message to her and it's coming from a guy who went to the same school as her YEARS ago..

I can't speak for anyone else. For me a person I met or knew from the past might represent an older part of my life or phase and I'm no longer the same person.

Different people are different and there are people who pop up again for many people. That's ok too. No right or wrong, I think.

I still say have a shot...Just as much chance as meeting a new girl really...The fact you went to high school together should actually be a good ice breaker...

If it doesn't work out it doesn't work out....

It's your lack of confidence that worries me a bit, whether it be with her or any one else. You're over-thinking it*

Carus*

I still say have a shot...Just as much chance as meeting a new girl really...The fact you went to high school together should actually be a good ice breaker...

 

If it doesn't work out it doesn't work out....

 

It's your lack of confidence that worries me a bit, whether it be with her or any one else. You're over-thinking it*

 

Carus*

I would not do it randomly. I would try to reconnect with something mundane - asking if she knew if they were planning a reunion or such to test the waters on social media but i would not ask her out. Who knows if he is someone she remembers from school. If they were actually good friends in school reconnecting would be different but i really think he should move on. She is not the same person she was in high school. She could be married, could be in a relationship, too. If they never really spoke in high school, it would be a huge no. if they were close in some way, he could say 'hey, you came up in my 'people i might know' on facebook so just wanted to say hello"