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General Dating Questions/Does nice/shy guy like me?


I've known this guy for around 6-7 months and we see each at a professional association meeting every week but we never really got to know each other on a personal level until recently. Last Friday afternoon, I visited his office and he opened a bottle of red wine to drink with me. He told me that out of all the times he's ever invited anyone to his office, he's never offered anyone wine and that I was his "first".

So while drinking red wine, we talked business (we were supposed to be meeting in order to learn about each other's businesses), yet we also spent alot of time talking about random things that got kind of personal. Like whether I like tall or short guys (he's tall) and when I said tall, he said "cheers!". And whether I play darts/pool (which I don't but he then offered to take me out to play it with him sometime). He made comments repeatedly about how our personalities were such a good match (he even initiated to "cheer" our drinks when he said that). He also referred to a couple of my newest facebook photos, he didn't "like" them so I didn't realize he was reading my facebook that often.

He later asked me if I was single which I told him yes. I didn't ask him back as I heard he was single too (At this point, with my whole married-guy fiasco, anyone who isn't married is already a huge sigh of relief! Though I can't confirm he's not casually dating anyone else, I'm pretty sure he isn't in a serious relationship at the moment either). Anyhow he commented that it seemed our mutual friends are bent on setting me up with this other guy (XXX) we know. He joked that I should consider XXX but I directly said "I hightly doubt XXX and I will have a future together, XXX knows this too and I'm really direct about things like this". He also joked that everyone in our association is only fixated on matchmaking me and XXX but ignoring him. I laughed and said its only cause he never speaks up and says he wants to meet someone.

Anyhow, initially he was supposed to have another business meeting with his partner that involved interviewing potential staff, but we got carried away from chatting and I kept hearing his phone vibrate. I asked him if I was holding him up and he kept saying "no its ok, lets keep talking". When my phone rang, I ignored it telling him it was likely just a cold call commercial and that I would call them back afterwards. He also said the same thing to me when his phone rang later on. After our meeting was over, I told him to invite me for happy hour with his friends next time so we can hang out more and he said sure.

Anyhow, he's the typical "nice/shy" guy you read about in dating forums. Question is, do you think that this "nice/shy" guy is just being friendly with me, or is he interested but is too shy to say it out? I told my friends about this guy and they seem to think that anytime a guy pops open a bottle of wine during a private business meeting alone with a girl AND asks if she is single means he is interested. Is this true? Any insight as to what this guy might be thinking?


It's hard to be sure, but chances are he is interested. Otherwise, it would be really hard to imagine why he invited you for wine and why he was asking you all kinds of personal questions.  
If he is indeed shy, it's possible that he is interested, but he didn't get a positive enough feedback from you in order to be sure that making a move would be appropriate. If and when you see him again, try to show a little more interest yourself in your own subtle ways, and this should help him have the confidence he needs to ask you out, etc...  



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