Dear Shyann,

From the way you wrote your question, it sounds as though there may be something more than friendship going on already.

Unknown Baggage

I believe something must have happened to him to make him say, "When you talk too much you usually end up messing up friendships". That's a strange thing to say. So he is either naturally very shy or maybe he has some baggage that you don't know about.

He Seemed To Like the Physical Contact

If you managed to make him smile and laugh which – as you wrote – he hardly ever does, then you must obviously mean something to him. Also if he let push his hair back and he smiled, then I think you're in with a chance because he seemed to like that slight physical contact between you.

I think that he believes he is boring and he is worried that you wouldn't like him like that so he wants you to tell him he isn't boring. That last sentence sounded a bit twisted, but it could be just a little bit true.

He's Shy

He's not shy. He's protecting himself.

About when you asked him if he wanted to go out somewhere with you and he said "Maybe, yeah", I think that he does want to go and hang out with you but he doesn't want to show it because he's so shy.

Go Somewhere Casual

So "Maybe, yeah" is pretty good for someone who is quiet.
Go out somewhere casual where he won't feel pressured.
You should go out somewhere together to somewhere casual so he doesn't feel so pressured as if it's a big date.
I think it's a great idea to ask him to meet you at State Park to just hang out because it's where you work and a casual atmosphere so he is less likely to feel smothered and pressured.

Tell Him You Want More Than Friendship

Tell him you would like more than the friendship you have at the moment and accept his response.

If he doesn't want more than the friendship you have and refuses, then tell him that you still want the friendship you had as it means a lot to you. If he starts to back away after that then talk to him and convince him that nothing has to change.

You said you were persistent so this will give you the chance to prove it. When he finally realises how important the friendship is, then it'll be stronger then ever.

Don't go over the top to be near him, though.

Don't Stalk Him

Don't start calling him all the time and trying to see him. He sounds shy and quiet, and if you start following him and calling him all the time, he will feel like you are stalking him. I had a bad experience with this, so just take my advice don't go over the top to be near him and to help convince yourself that he really does like you, which he doesn't if he said no.

Go Out as Friends

But it's worth the risk. She should just go for it.

If you decide that you don't want to risk the friendship with something you are not totally sure of; you could still go out together as friends. It would be hard to be friends with someone you want more from, but when you move on you could find someone you wouldn't have to worry about, (too shy, quiet and risky) keep a good friend and have the bonus of a new boyfriend.

Overall I think you SHOULD take the initiative and ask him to go somewhere with you, as I am pretty sure you won't regret it.

– Heartache