Not really sure what to think here.

[bebeblondie]

So there’s this guy, who’s a very close friend of my best friend’s husband, we’ve known each other for about 10 years now. When we first met we hooked up a couple of times (I think he liked me more than I liked him), but then I ended up getting into a serious relationship with someone else (that lasted about a year) and we never hooked up again. I know him fairly well, we’ve even been on vacation together twice with my best friend and her husband (the one who he is close friends with), but it was strictly as friends. In the past couple of years I’ve only seen him 3 or 4 times, however a couple of weeks ago was the first birthday party of my best friend’s son, he was there and he seemed to be flirting with me, the best way he knew how since he’s pretty socially awkward. He kept trying to engage me in conversation with him, but other than that nothing really happened other than him kissing me on the cheek goodbye (which is pretty normal amongst all of us) and then when he went to say goodbye to couple of other guys, I walked over to say goodbye to them too (since I was leaving as well), and when I finished saying goodbye to them he was standing there and just threw his arms out in order to hug me goodbye again, so I hugged him, and he squeezed me tight (but he always does that whenever we hug so Im not sure if that means anything). Anyway yesterday was my birthday, and since we are friends on facebook he wished me a happy birthday on my wall, and I commented saying thank you. He then private messaged me wishing me a happy birthday again and saying he owes me a birthday drink. Now normally I wouldn’t really call this flirting, but for a guy who is extremely shy and socially awkward, do you guys think this would constitute flirting/interest?

[vesper]

he is flirting !!

[LoveSoDeep]

Yep....I think the last PM to say he owes you drink was actually his way of asking you out for a drink. If you like him then take him up on that offer!

[bebeblondie]

Well I did respond thanking him again and saying "yes you do " and haven't heard anything from him since but that's typical of him because he's so shy and awkward

[LoveSoDeep]

Give it few days and then maybe send him a message saying "so when do I get to cash in on that drink offer?" Since he's so shy it may not be bad idea to help him along.