frustrations of flirting

"If I'm overtly flirting with someone, they've already been friend-zoned."  - Annie

Flirting is fun, there's no doubt.  Flirting with someone who flirts back is even more fun.  But Annie has a point - it's easiest to flirt with someone you don't really like "that way."  When you know someone is just a friend, it's easy to be a little outrageous, because there's no risk.  You're friends, and you're unlikely to spoil that friendship with some silly flirting.  But when it's someone you like?  Whole 'nother story.

I called another friend today to pass the time on my long drive home, and she brought up the same topic.  Why is it so hard for us to flirt with someone we like?  I think there are two reasons. 

One, and this applies to everyone, is the risk.  When flirting with someone whose interest you desire, you have something to lose.  This could be your one chance to prove how interesting you are and convince them that they want to spend more time with you.  And if you're like many of the rest of us, your mind has a tendency to go to mush when confronted with the object of your affections.  Words slur, thoughts don't come, and your mouth opens wide enough to insert both feet.  Or you are just so afraid of saying the wrong thing that you don't speak at all and come across as unaccountably shy.  Either way, you generally leave the encounter full of  ''if only''s and feelings of general inadequacy.  Now they'll never be interested, because you've shown you aren't even capable of normal human speech, never mind dazzlingly witty repartee.

Two, as girls, we're culturally condemned to holding back.  Before you even say it, I know that lots of guys say they'd be okay if the girl made the first move, or that they wish girls would be more obvious about their interest. There are silly little sayings like this floating around to enforce that message (and they make a good point, but....)

But in my experience, that's bunk. Too many times, I've seen a girl take initiative and be bold with her interest, and the guy immediately backpedals. She then gets blamed for coming on too strong, or for being too forward.  Too often, when a girl pursues a guy, he imagines that she's clingy or just infatuated and he backs off so as not to encourage her.  As much as I hear guys talk about how they'd like girls to speak up more, when I see girls go for it, the guys run, and the poor girl is left there wondering why she took that stupid risk in the first place.  No matter what those guys say, their actions are significantly more convincing, and so we retain our fear of flirting first.

I don't have some grand conclusion to come to, here at the end.  I clearly don't have this flirting thing figured out right, as my eight-month date-free streak will prove.  I just felt like rambling about it a little, since it's come up so frequently in recent conversations.  I'd love to hear your thoughts, oh audience.