I fancy a flirtatious friend...

I know this sort of question gets asked a lot, but there are some extra complications in my case, so just try to humor me.

Okay, I’m a 16-year-old girl. I have a guy friend—let’s call him “Fred”—who I have had feelings for a year or so, but in the past month they’ve become much stronger. We’re not extremely close, but we are reasonably good friends, I think.

“Fred” is friendly towards me (invading my personal space, finding excuses to touch me, staring at me, etc.). Sometimes he’s very nice and a perfect gentleman, but at other times he’s playfully cruel (he’ll tell me I’m a dunce, etc.).

The trouble is that he’s just a flirtatious sort of a person, so much so that I know of a number of other girls who have fancied him at one point or another. In fact, Fred can be so overly-friendly that I once heard a guy who is friends him wonder if he is bisexual.

But the plot thickens—Fred fancied and dated one of my best friends for a while. He broke up with her less than a year ago, and I know that she still has feelings for him and would get back together with him if she could. She doesn’t know that I’m very attracted to him, needless to say. (No one does, actually, and it’s driving me crazy having to hold it in.)

And to make things even weirder, about two years ago I fancied Fred’s elder brother. Fred knows this, and he used to have great fun teasing me about it (until recently, that is, because this brother is now in a serious relationship, and I’ve recovered from my attachment to him, anyway).

I don’t know what to do. I wish I could muster up the courage to just tell him how I feel, but then I think maybe I should try testing the waters more by being more flirtatious myself. I’m a naturally reserved sort of a person, and it’s hard for me to just open up and let my feelings dictate my actions. In fact, I fear that I may actually act even more aloof around him than is natural, just because I’m afraid of being friendly and then getting rejected. (Or having my close friend who used to date him getting mad at me for flirting with him, because, as I said, she still seems to have feelings for him.)

I’m really very sorry that this post was so long. Thank you for taking the time to read it.

Any words of wisdom or advice would be greatly appreciated!

Heh heh...good luck with that.

Take the risk.

It's better than sitting and watching and missing out on your oppurtunity, if it exists. Go for it. Your friend should understand if you end up dating him, because, that's what a friend is for. If she doesn't, than she isn't a good friend.

Go for it.

couldnt agree more with bando man, you should take the risk rather than leaving him alone and torture yourself. I KNOW that it's not easy to tell a person how you feel about him but if he turns out to have the same feeling as you woulnt that be great? there is a risk for evertyhing so pick the right time to tell him how you feel... good luck! :)