How do I get close to him?

[darren23a]

Hey guys,

So there is this guy that I want to get close to but i'm not sure how to facilitate it. It's a bit of a story but bear with me please

He frequents the same gay bar as I do and he's always really quiet, he just sits at the bar and nurses a drink all night. He often looks lost in thought and kind of sad so i've asked him if hes ok a couple of times to try and start conversation and he always smiles and says he's fine then goes back to drinking. I'm not sure if he's shy or the strong silent type or just wants to be left alone.

I was asking the bartender about him and found out that he lives with another one of the regulars at the same bar that I sort of know. His flat mate is the polar opposite of him and is loud, gregarious and always the centre of attention. His flat mate has made it clear that he has a crush on me and has invited me around a few times but i've always made excuses as I don't fancy him back, although I do find him a fun guy.

I was chatting to his flat mate one night and he invited me over again and I decided to take him up on the offer in an attempt to try and bump into my crush and try and get to know him a bit better. The first time he was at work (doh!) but he was there the second time and all three of us sat and had dinner. He was polite and friendly but again quite quiet over dinner but his flat mate tended to dominate the conversation. He's clearly intelligent as when his flat mate gets political he talks a lot more so it's not as if he's quiet because he's stupid or has nothing to say. He made a couple of jokes which were funny as well so it's not like he's humourless either. At the end of the evening, I gave him a farewell hug (yay!) but left kind of frustrated because I didn't really feel as if I had got any closer to him.

I was thinking up a new way to try and get to spend time with him when his flat mate invited me to join him and his friends at a restaurant to celebrate his (the flat mates) birthday. I could see from the guest list that my crush was going to be there. I got to the restaurant and promptly sat myself next to my crush and planned to engage him in conversation but he spent the entire meal talking politics with his friends across the table. I don't know enough politics to join in and didn't want to look silly. His flat mate kept talking to me throughout the meal as well so I didn't really get the chance to talk to him either. We all went quiet at one point and I sort of randomly told him that I thought he was a lot younger than he was when I met him and he just looked confused, smiled and said thanks. I could have died of embarrassment.

Anyway, we all went to a bar after the restaurant and he went outside to smoke and so I went outside and sat with him. He offered me a cigarette and I took one, even though i'd given up smoking (shallow I know). We sat in awkward silence for a bit and then he asked me about my studies and I went into detail about that, I was so nervous that I kept repeating the same thing over and over again. He smiled and offered some advice and said that he was glad that I was doing something that made me happy. In my drunken state I tried to let him know that I liked him by dropping ever so subtle hints like 'I know i'm only 20 but I would have no problem dating a guy who's 30.' (He's 30 by the way, although he looks about 23). He just smiled and sort of laughed and said 'ok'. We finished our cigarettes and went back inside.

I missed my last train home that night and so his flat mate offered me their sofa for the night. The three of us went back afterwards and had some more drinks back at their flat. I tried to steer the conversation around to relationships and romance by talking about past boyfriends. He was quiet again once we got back but he did say that his longest relationship was for 8 years so he's definitely boyfriend material, although he says he's not very romantic, he doesn't like to cuddle in bed all night We all went to sleep and I left in the morning for work, I let them know I was free throughout the week to meet up but I've not heard anything since other than a couple of messages from his flat mate on facebook regarding the night out

I sent him a friend request on facebook which he's accepted but I don't know what to do now, I think he knows I like him but he's not making any moves or acknowledging it, does he not like me? Am I wasting my time? Is he shy? Am I not clever enough for him? Is he aware his flat mate likes me, so is he trying to avoid conflict? So many questions! Any advice guys as to what to do next would be great please please please xxx

[jimcrackcorn]

Ok,,, call him up and ask him if you can come over and have a talk. Then go out and buy a single red rose. When you get to his place, ask to come in, and then give him the rose and tell him that you don't know how to say this properly,, but you really like him and would like to go on a date tomorrow night (or whatever day you figure is best for both of you).

The ball will now be in his court.

He will either accept the date - at which point you will get all happy,,, or he will decline and give you an explanation as to why he can't.

The whole point is to make him aware of your intentions (romance & relationship) and then let him take it from there.

The rose is important because it lets him know that your not looking for just a hook-up, but something more serious.

Good luck,
Jim

[Lexington]

Honestly, it doesn't sound like there's a lot of interest coming from his end. You've offered several openings, and even semi-blatant come-ons, but he hasn't responded well to any of them. In addition, all of your moves to hang out with him probably are coming across like you might be interested in the flatmate instead.

I'd say go for broke. Send him a message on Facebook, and ask him out. Make it clear that's what you're doing, not just "I've got an extra ticket for something and wanted to know if you wanted to come along." Ask him out on a DATE date. He'll either accept or turn you down. And if he doesn't suggest an alternate day to go out, consider that a "I'm not interested".

Lex

[Borg69]

I kinda agree with Lex... You're throwing it out there, but still really don't know much about him or what his type is or what he's looking for. You also have the other one cock blocking and interested in you.

What do you see in this guy? In your OP it kinda seemed like a pity thing?

[Radbot42]

I agree and think you should just tell him you like him and ask him on a date. Do so in whatever way is most comfortable for you.

[Darius]

Honestly, he sounds really boring. Add to that he doesn't seem too interested, but that might not have to do with you. Maybe he is not ready for a new relationship.

[darren23a]

Thanks for the responses guys.

To answer the question about what I see in him. As shallow as it seems it's mostly because he's cute, totally my type. I like that he seems different from everyone else, like more grounded, laid back and mature despite looking twinky. I think I made him seem worse than the reality. It's not pity and he's not boring, he seems really intelligent and from some of the things he's said he seems quite cultured. He goes to the theatre and opera and travels a lot where as most guys I know just go to the club, take drugs and get drunk which I personally find really boring. He's well known in the bar and he talks to a lot of the regulars, I think I made it seem like he's an antisocial loner. I know lots of other guys fancy him but he's not dated anyone at the bar as far as I know so I really don't know what his type is, I could ask his flatmate but i'm not sure if that's appropriate?

I think i'm going to have to follow your advice and ask him on a date but i'm really worried i'm going to look stupid Oh, and Jim, I can't do the rose thing, when we were talking about romance his flatmate was explaining how he laid rose petals on the bed for his ex boyfriend and my crush said that he thought it sounded unoriginal and tacky (not in a nasty way, they were bantering with each other) haha!

[Darius]

Show him your wiener.

[JohnSomebody]

Actually what I gather from your initial post, I tend to believe that this guy dealt with a lot from his last relationship. It seems that he wasn't the one who ended the relationship and because of however it ended...he suffered a broken heart. The reason I came to this assumption is because I knew someone of similar character. The only thing with the guy that I knew is that he was really quick at assuming things about me that was totally untrue and furthermore...what I found disturbing is that he never took the time to get to know anything about me in regards to my likes, dislikes, personality, etc. However, even after a couple of times of finding out that his assumptions about me were false...this did not stop him from this behavior. Therefore, I came to the conclusion that for him to be attractive and single and did not date at all..apparently he suffered a bad breakup as well as heartbreak which results in him not being able to accept compliments or nice gestures from someone else without becoming panicky or drawing false, negative assumptions. With that being said...I would suggest that whenever you come in contact with this guy again...let him know flat out that you find him attractive and want to get to know him better by spending alone time with you i.e., going to the movies, dinner, etc. if he allows you to do so. With you letting your feelings being known to him...the ball is in his court and from his response/reaction will let you know where he stands or if there's any indication that he will show some interest in you. Good luck!!!

[Pyromancer]

If I knew that my roommate had a crush on someone, I'd be strictly hands-off with that guy no matter if I was attracted to him or not. Also, the age difference may not bother you, but it might bother him.

I agree with John and the others, you need to simply ask him out and see what his response is.