How should I approach this?

[mijo]

Ok, so there is a guy who I am friends with - he is best friends with a couple of my really good friends. He lives in the next city to us but has recently been spending more and more time coming over and coming out with us. He is 31 (I'm 24) and really really shy. After spending more time with us he has started to open up a little bit, but he is still very very shy and he has said that he is ridiculously shy when it comes to women.

 

I like the guy and people have said that we would be really good together as we have so much in common etc. I have recently broken up with someone but have mentioned to him recently that I'm ready to move on etc. He was over our way at the weekend and on Friday evening I spoke to him and mentioned that we were going out on sunday night and he said he'd have to head home as he had work monday morning. Then when I arrived at the bar on sunday I said to him that I didn't think he would make it and he said he had wanted to come down but would just stay for a couple of drinks. I said he should stay as it'll be a good night and then he smiled and agreed and said he could just leave earlier in the morning to get back for work. Everyone had a really good night and I tried to chat to him a lot and also gave him a kiss on the cheek as he left - which I don't do with any of my other male friends.

 

He is coming out with us on new years eve and I was just wondering if anyone had any ideas on how I should approach it? I spoke to him last night on facebook chat and the conversation got on to relationships. He said that he always likes to get to know a girl first but then just consider him a friend and nothing comes of it, then he said he had been single for so long that he was on the verge of giving up (his last gf was 6 years ago). I spoke a little about my ex and I said that I always get the wrong men, and he commented "well I think we should both do something about this situation". I complimented him a bit saying he should be more confident as he has a lot going for him and he said he can't wait for new years eve, he said "it'll be a great night, who knows what might happen but lets make sure we enjoy it". Anyway I feel like he has started to open up to me a little bit but this might be just because we have been hanging out more...

 

Just wondered if anyone had any ideas

[alli]

I say kiss him at midnight!

[Scorpion Fury]

^^^ ya what she said. do it. DO IT

[mijo]

will it not seem a bit full on? I am not certain if he is interested in me like that or just as a friend?

I suppose I could make sure I am next to him at midnight at least and see what happens...

[Scorpion Fury]

sounds to me like he is

 

you could do that, and joke around about kissing him at midnight and see what his reaction is...

[aesiir]

although it seems really head on/aggressive, I think you should do it! It sounds like you already have a pretty good relationship with him(even though its not really a "relationship" yet). Then again, if we are misunderstanding and you don't think you're on good enough terms yet, probably a bad idea to do something that risky. My opinion really isn't worth anything though.

[alli]

Well don't stick your tongue in his mouth. Just a soft, short lips-closed kiss. Then move away slowly & see what his reaction is & if he leans in for another.

[paperneck]

you're too worried about being certain. take a risk.