Search Results: flirting makes me uncomfortable

Okay, here's the situation: I go to community college and so does a guy i knew in highschool. He was always so so shy, albeit sweet, and I was very outspoken, a cheerleader, and I also had a 'sweet girl' reputation. I got to know him on the grad night actually, during the party afterwards. I asked if i could sit by him on the bus and we hit it off so naturally and effortlessly like i'd never had before or since, and i ended up falling alseep on him totally not trying to flirt or anything and he didn't wake me up and draped his jacket over me. Gentleman. I was kinda sad the next day that I hadn't gotten his # and I looked him up on social media which HE DOESN'T HAVE. -_- So I chalked it up as a loss after asking around and no one had his number or anything.

So a week ago (It's been 2 years) I saw him at my college and was unable to catch up to him before he went in a class. So naturally I stalked the heck outta him online and found zilch. I think I can catch up to him maybe, if i time it right, but I'd only have one chance to talk to him. I don't know if he has a girlfriend, or if he will be transfering, or if he even thinks i am attractive so I'm wondering what I can say in a one minute conversation to ask him out/hang out that wouldn't scare a super shy guy away and make him feel really uncomfortable. I would go to his friends but i don't know them well and only keep in contact via social media and it would feel weird being like "hey remember sophmore biology oh and give me your cute friends number"