That was just a little more than just a little unexpected

He's probably one of my best friends - not that I'd ever admit it to him. We ride the same bus at school, and he and my cousin love to torment me and pull my hair on the ride home.
This summer we added each other on MSN and have been talking A LOT.
He's gonna be a senior, me a sophomore. He has a girlfriend who's two and a half years older than he is.
Today, we were playing Truth (it's like truth or dare, except there's no dare), and he asks me how, knowing the whole lisa (his girlfriend) thing, if that were to end badly, what would i think about him hanging around me more. I was like what do you mean. He was like 'if I were to take you to a movie or something' I asked 'like a date?' his reply 'mayhap'

SO was not expecting that. I mean, like...idk. Haha if you're reading this, you should know, he's like a big nerd. I'm kind of a nerd too, but not. I do well in school, but I'm friends with like everyone in my class.
It's just...weird. I'm not gonna think about it when I talk to him though, cus he thinks I'm like completely unfaz-able. Which, when I'm around him, is true.

This is very...strange.