i have a bit of a dilemna

there's this guy i've been friends with for around 3 years. when i first met him i really liked him, but some female friends of his told me he wasn't interested. i ended up seeing a friend of his for about a year, although it wasn't anything serious (i didn't like him very much, i was lonely, it was stupid i know) . the first guy moved away after we finished uni, we stayed friends but i didn't see him all that often.

now though we live in the same city again and we're spending quite a lot of time together and i've realised that i still really like him. and also another mutual friend said that the people who initially told me he wasn't interested might not have been honest. this friend thought that he did like me too when we first met.

but i have no idea what to do. we've been just friends for 3 years. if he doesn't feel the same way then it might ruin the friendship? also he might not want to go out with me because i stupidly went out with his friend (although that did end 2 years ago)?

what would you do? i'm terrible at this stuff.

Just flirt with him a little, and see if he flirts back. That's a pretty easy way to find out if he likes you.

well, i've tried that and he sort of flirts back but it seems like a joky thing. i don't think he realises i'm serious. also he can be quite flirty with some other girls we know, but he's told me before that he's not at all interested in them...

he's been single for 5 years. i think he's even more awkward with this stuff than i am

You're right to suspect he's awkward with this stuff if he's been single for five years. He might have told his female friends all that time ago that he's not interested in you, but he might have been saying that because he was afraid you wouldn't like him back. Since you were going out with his friend, he probably assumed you weren't interested and was afraid of making a fool out of himself. Personally, I tend to deny liking people because I'm afraid of the awkwardness. If anything does happen here, it'll probably be because you made the first move. It sounds to me like it's a matter of risk here. If you want to find out if he's interested, ask him straight out. You'll be risking your friendship, but I doubt he's going to swallow his insecurities and make the first move if you don't. If he does like you, he's probably longing for you to make the first move, and nothing would delight him (and scare him!) more than you liking him back. Ye are mature, I'm sure that if ye're friendship is really worth it, ye will be more than adept to put aside the awkwardness if he does reject you. Confidence can be feigned more easily than you think in these situations.

I agree with ShyViolet in that you should keep flirting with him for a while. If he didn't want anything to come out of it, he probably would have acted differently due to the guilt of not liking you back.

You could be totally spontatious and do something cute like send him a love note.

Ok well you need to take your flirting to the next level, make it just a little more obvious, and then see what his reaction is.