Shy guy confusing me - help!

[soupin]

Okay so I apologize - this is a REALLY long story but I need to lay it all down because this guy has me thoroughly confused.

 

So there's this guy who I met last summer while in Alaska. He's super nice to everybody and everybody loves the guy but he can also be super shy and quiet. My friends and I made friends with him that summer and I did what could be considered mild flirting (i.e. he stared at me a bit, there was some gentle teasing, etc.). He was kind of off-limits though because he was getting over this other girl that he had a crush on in Alaska (nothing ever happened between the two, but he liked her and she got a boyfriend so it broke his heart). Upon return to college/work (he went to the same college and currently works on the same floor as me), we only hung out once at a concert with the same group of friends - however, I caught him staring a long, deep stare at me from his car upon parting for the night. After that, I didn't really see him much my whole senior year since I was so busy finishing up my degree so I assumed his attraction was either my imagination or it wasn't meant to be. The longer I didn't see him though, the more I started to like him.

 

WELL, after he left for Alaska again this past summer, I caught him on Facebook once. We chatted online a bit and I even joked that he should make me something while he's up there (he likes to carve stuff). I still fancied him a bit, but I assumed that he didn't feel the same way. BUT, shortly after he returned to work back home, while I was out of my office for about 15 min, (according to my coworkers) he was "shoved" into the office by his best friend looking incredibly nervous and was looking for me (whilst his friend hung out outside looking all mischievous and inquisitive through the window). I ran into them while I was coming back up the stairs - he was really shy and quiet while his friend was acting really awkward in front of me (something he NEVER does - he's the outgoing type that I had known from the year previous). Nothing happened besides a 5 minute "how was Alaska" conversation but, when I moved my car later, the shy guy was also moving his car and he gave me something he carved while in Alaska! From then on he mustered the courage to go into my office to say "hi" a couple times and try to ask me to go for lunch with him. I was busy so I compromised by asking him to get coffee with me sometime which we promptly did a day or two later. We've been getting coffee once a week since then (by the way, he also doesn't ever go to coffee shops alone - when we went it was literally his second time he had ever been to a Starbucks...I also think I may have accidentally started a coffee addiction), however, it's been mostly me initiating the coffee outing (although he never refuses). We text a lot, chat on facebook sometimes. We've done lunch and dinner once or twice and I've been to a concert with him. However, I'm not sure if these have been dates or just friends hanging out time. He even gave me one of his shirts! (although that was related to an inside joke while in Alaska).

 

He's also REALLY good friends with one of my good friends (who already has a boyfriend in a long-term relationship). They hang out a lot and enjoy each others' company in a kinda brotherly/sisterly way. I've have been hanging out with him and this mutual friend as a group almost every Friday where we go to a driving range or bar or something. I kinda feel weird when we're all together because he's still so quiet and shy around me, but acts like he's around one his guy friends with her - I don't know if this is because he doesn't like me and likes my friend more or if it's because he's nervous around me because he likes me. This friend knows him very well, and she says he tends to "clam up" when he gets anxious or wants to hide something. She knows I like him, and she has told me she has always had a "feeling" about us two (she used to tease me about this during my senior year). I once asked her to ask him if he liked me, and she said he responded by "clamming up", smiling, and, after a pause, responding with "I don't know...she's really nice, but, I mean, I don't know her that well yet." This just tells me that he doesn't even know if he likes me at all.

 

Even more confusing, while we were at a restaurant last week, he intentionally told me he has never had a real girlfriend before when talking about how different he was from his "ladies man" brother. I responded by telling him I never had an official boyfriend either to make him feel more at ease. I thought maybe he would springboard this into a conversation, but he never did.

 

So, does this guy really like me? More recently, when we make plans to do something that I think will be just me and him, he'll assume this mutual friend is invited too. While I love her as a dear friend, I can't help but think this is because he doesn't want to be alone with me. He might be using her as a security blanket to avoid the awkward feelings around me or maybe he just wants her around because we are all friends. I've heard somewhere that shy guys tend to ignore the people they like when they are with friends for some reason, but I don't know why he would want to intentionally create a situation like this. Should I assume he just wants to be friends and hope for the best? I'm this close to asking him outright if he likes me, but I don't want to scare him off since he's so shy and especially if he hasn't sorted out his feelings yet. Help!

[sidehop]

All point indicate you two just need to break the ice and go out. Go have fun and forget who likes who. It's a bit obvious but someone just needs to spill the beans. But by all means, go out together alone first. The rest should just flow with ease

[soupin]

Thanks for the reply. I guess I should spill the beans But I have to ask, should I wait for him to do it? Or do you think it will never happen unless I do it since he is so shy. What I mean to ask is if a shy guy will ever get enough courage to tell me how he feels, even if it takes a long time. It sounds pretentious but I'd much rather have him tell me since I'm kind of old fashion and it would mean so much more to me...