thats real nice to say the second u meet some1, and i already kno hes single cause natalie refused to go out with him, and i think he would be kinda weirded out if i went up to him and said 'hi, will u go out with me?' he might think im kinda crazy, which i am, but aside from that, u usually have to kno the person for a little bit before u ask them to go out with u...
Even after years of knowing someone, do you really know them? The answer is no, so if there is chemistry on the first meeting then that's as good as anything to gauge if it'll work. IF and that's a big if (in case you didn't notice), IF you do get to meet him, just ask away, if you don't ask then you'll never know.