I looked up his family before and it popped up when I was with him
I had a guy I was just starting to see over to my "place" (ie. dorm room) to watch a movie. He started telling me about how he works for his dad in the summers, and his family owns the company. He decided to show me his family's company website, and when he started typing the address in, it popped up automatically. Because, of course, I'd been googling him and knew all about it (although the whole time he was telling me his story, I was pretending I knew nothing). He just said, "uh...that's...weird". I said "uh..yeah...". Awkward silence for a couple of minutes.
It didn't work out, and I haven't seen that guy in years, but it's one of those stories where I still cringe every time I think about it.