I've said it before, and I'll say it again:
Don't date your friends.
Just don't do it. I know it's worked fine for some people but so does eating scrap metal, okay?
When dating (in the interpersonal relationship sense, of course) someone, there's one very important thing to make sure of:
Whatever you do, make sure both (or however many) people involved know that they're dating. Otherwise, you can be in for some sticky, sucky and even regretfully sad situations.
In high school, I had a really good female friend. She lived around the corner and a couple blocks away, so we started carpooling during the upper-class years. How the friendship developed may well have started with that, but I'm pretty sure I knew her well before we drove each other to school in the mornings.
I thought it was a great friendship. She was smart, great-looking, funny, ticklish and I loved spending time with her. I got along with her other friends, too... even though they were in The Band. We spent so much time together, in class and out, that I became some sort of honorary band geek in the eyes of some. We were in all the Enriched classes together, we played Hearts in study hall, we sat at the same lunch table when we both had it at the same time. We did projects together for classes--I remember well a presentation on Singapore for which I spent my first over-nighter procrastinating, and for the same class a "let's pretend you're getting married and get jobs and need to make a budget" sort of thing also--though we didn't study together, since nobody needed to study in high school.
After school, some days we'd just go back to my house and into my room and have tickle fights before I dropped her off at home, and on the nicer ones we'd stop at a nearby park and swing on the swingsets and enjoy each other and life in general.
I thought it was a great friendship. Of course I asked her to our Senior Prom. It was patently obvious to even the densest of our friends that we were inseparable. As the big day started coming closer, though, things started to get weird. Really weird. She started talking about another guy she'd started hanging out with, this guy in band that seemed pretty cool. We stopped having so many tickle fights, and the wonderful feelings of, well, whatever it had been weren't so present as they had been.
I started to get a little concerned. Was there something wrong? What had happened? I knew I'd done some bad things lately like changing my opinion on albums I'd been critical of, and I'd left her at school once, but what did that mean? I started to ask our mutual friends some questions, and then things became much clearer and, at the same time, uglier.
It turns out that she decided that it was workable to date two fellows at the same time. When I heard this from our friend's lips I was taken much aback.
We were dating?! Why hadn't anyone told me?!
Being the idiot that I was, I never directly confronted her about this. I never sat down to set the record straight, to make sure we were on the same page.
Prom came and went. We went with in a group of friends, she was radiant and I was dapper in a rented tux, dinner was good, the dance was normal, but she declined to come to the amusement-park for the after-prom party. I went anyway and had a blast, but that's irrelevant.
I had thought that we'd had a great friendship. Somewhere along the line (that to this day I still don't know) it became, for her at least, a dating relationship. My weak objections to her dating two guys at once were shared by some of our friends, but an obvious solution soon presented itself: She "broke up" with me.
Which was fine for her. After all, she was dating me. But I wasn't (consciously) dating her. Understanding too well the rules of breakups, though, I had little recourse but to see the end of the great friendship I had cherished and then likely destroyed. Tears and sleepless nights, yadda yadda yadda, and then the school year was over, we graduated and I went off to Illinois. I've only had two cordial but mostly superficial conversations with her since, and still pine for her. I miss her, damnit.
So whatever you do, don't date your friends. And when you do date anyone, make sure they know it too.
Otherwise, it just hurts too damn much. It's about the only subject I can give advice on, and even then, nobody follows it.
I've said it before, and I'll say it again:
Don't date your friends.
Just don't do it.
Don't date your friends.
Just don't do it.
Annie, I miss you so much... I'm sorry. | 
