Search Results: dating a shy guy

So I've had a bit of a crush on a guy friend for a while and I think (or at least thought) he kind of likes me too. Right now it's very early days but I was telling one of my best friends about it and she pointed out that I'm taller than him and said it would be weird if we dated. Now I'm just over 5'8 which is not huge but pretty tall for a girl, and he's just under 5'8. I honestly hadn't really noticed until she pointed it out since I know him from school and I'm used to seeing him when I'm slouched over with a heavy school bag on my back, but now I'm worrying he'll have an issue with it too. It's not really very noticeable unless I'm wearing heels but I love heels and as an ex-short person (I was 5 foot nothing until I was 16) I love being tall and being able to see over heads in a crowd is still a bit of a novelty for me. I've kind of come into my own in the last year a bit (I grew eight inches and have boobs now) but I've liked this guy since before that and in my head he's still taller than me... I guess I was wondering if there's any point hoping it wouldn't be an issue for him? How would you feel about dating a girl taller than you? Especially if she was unwilling to give up high heels? I know I should probably just ask directly and try and be subtle but I've been told in the past I'm about as subtle as a rampaging elephant and I'm kind of shy and scared of rejection. I guess I was just wondering how would most guys feel about this?

I started noticing a guy at my gym look my way a lot, not sure if he stares at me because Im in my own headspace. He always says good morning or hello to me whenever we see each other. He is hesitate to look at me in the eyes though. I decided to start a conversation with him last week when I entered the gym and as I left he started one with me at the front counter (I was leaving).

He is young (20) so I am assuming he doesn't have a lot of dating experience. After the conversation last week he only greets me and looks away from me when I catch him glancing at me. I've had my headphones out so he can talk to me but he doesn't.

What do you think?