Well I was talking to this guy I know since high school 9th grade I called him a sexy *** is that weird? You think he felt weird I'm like a really bad flirt!

If your reaction to an offhand comment was as random as this question then yes, he was probably a little freaked out. If you just laughed it off as a joke, then it was probably fine.

It is not weird to make comments like that to people you know for a while (who are good friends).

As Flirting, it's all in the way you said it.

You could easily ask him if he was uncomfortable with it and then stop.