I've never interacted with Chris before, but I've thought about what I might do if the opportunity came across. (I have family and friends in Virginia who live not too far from Chris' stomping ground, actually, and I visit them fairly regularly, so it's really not too much of a stretch... well, far less of a stretch than if I just kept myself secluded to my hometown in PA.)
I actually fit his sweetheart requirements to a T (except that I don't have a car or stable income (yet; still in school), nor do I live near Ruckersville), so I used to be kind of terrified of what I would do if he approached me and tried to convince me to go out with him. After doing some more reading up on him though, I realized that he's too passive for that to even happen in the first place, haha.
But what would I do... I don't have the acting abilities (nor the heart) to string him along in a lengthy trolling attempt, so I just I'd just try to chat with him for a bit, get a StreetPass tag and maybe a picture with him, if I can stomach the smell. It probably wouldn't result in anything monumental, but it would be enough for me.
One of these days when I'm down in Virginia, I want to go to the Game Place (or whatever it's called now) and do some TCG shopping there.