Search Results: should i ask him out girls

There was a woman I knew from grade school, that remembered me, and sent me a Facebook request. I accepted it, and then I added her on Snapchat. Some months after that, she responded to one of my snaps stories, I think I said something that could have been construed as being hard on myself, and she just said something nice. I explain the rest short and too the point

I started to comment on her snaps more often, I don't know why, because I don't see her in person, or know her like that, and she would respond every time.

I then started to like her, I would basically tell her that she looked pretty a couple of times, and she would respond with hearts each time. I would also comment on stuff other than her appearance, and she appeared to enjoy talking to me. Would use emojis, exclamation marks, semicolons, said a decent amount most of the time, and the other times she would just like the message (if there was nothing to say I guess). Also would say more than just a simple thank you when I would compliment her. Would be like a thank you and the something else after it.

She frequently watches my stories, I don't know if its because she's just curious, but she replied to a few more of my stories and complimented me a couple more times, saying she thought I was nice, sincere, and she thought something about my appearance looked fine (I think it was my hair, cuz I cut it, and posted it for no real reason, just having fun, and she basically said it looked better before I cut it, but that it still looked fine. I figured she was just being nice, and trying to make me feel good. She never said that I was handsome or anything, so I figured she doesn't find me physically attractive. She never asked me out on a date either. Should I still have asked her out? I don't want any girl to be potentially upset, and feel like you can't even be nice or have casual convo without someone making someone more of it, if they don't feel the same way?

He's in his 20s, introverted, has been checked out at least 5 times, hasn't actually dated, but has had at least 2 girls that knew him like that, that have had a crush on him, he got hit on by another guy, two women that were strangers told another guy that they were trying to holla at him, he was told that he can find a better looking woman, when someone claimed that he had a crush on them, that he should try to get one of the "cute" girls, that worked at a certain restaurant, some women seem to watch him very closely on social media, when he does go out, generally women make eye contact and smile at him, but some don't even make eye contact with him. He's been rejected a couple of times, but the last time was 8 years ago. Hasn't asked anyone out since then.