Eh, that's just my opinion... but you will also never EVER see me use lol (except in this explanation). It just seems juvenile.
I agree with this. It's hard to tell how much it bothers other people because so many of them do speak like that online (especially via IM, which is why I refuse to use that shit) but either way I think overusing emoticons and things like "lol" can pretty easily make you sound like an idiot. When I was in college I remember being amazed by how some of my otherwise normal and intelligent seeming classmates would turn into blabbering idiots trying to bury you in a barrage of smilies as soon as you put them behind a computer with MSN.
Anyway bluewizard, I agree with Zeph. Don't ask so many questions about mundane stuff. Instead you could, I dunno, be friendly and compliment her on her appearance or something (without making it sound like you jerked off to her MySpace photos just the other day, this is important).
Thats one ugly bitch.