Sooo.... am I just overthinking it?

So I was affected by the snowstorms that hit the northeast of the US. We had a lot of trees go down, and one was hovering over our house. We called the tree service to come take it down. Well, I called my friend over to get the phone, and one of the guys looked at me, and kept walking. I didn't think anything of it. He went up to my friend after I went inside, and asked if I was so and so, to which she said yes. He then told her that he remembers when I moved here in 5th grade, and that we graduated high school together (I'm 23, 6 years out of high school). She told me this, then my other friend went out and asked what his name was, since nobody knew. He told her, then said I probably wouldn't remember him because he wasn't very popular (which he was, and I wasn't, and we've inadvertently hung out in a group before). But I'm kind of confused as to why he'd bring up me moving here and graduating together to someone he doesn't know. They keep telling me to talk to him because he's interested, but I'm also shy and don't really want to be shot down... So, I'll take an opinion from those that are looking from the outside.