For me, the best way to get over a phobia is to force myself to confront it by forcing myself to do the things I'm afraid of.
In real life, the worst case scenario is never as bad as it is in my mind.
What is the absolute worst that could happen if you approach a guy? He'll reject you? Laugh at you? First off, men very rarely reject a woman who has approached them. If they do, they'll likely aplogize for it. "I'm sorry, I'm married", or something along those lines. It's never as bad as we think it will be. But most of the time they'll be so flattered that an attractive woman like you has approached them, that they'll be the ones embarrassing themselves.
It's not desparate to approach a guy, it's proactive. You're simply increasing your odds of meeting someone by taking matters into your own hands.

Start by practicing on people. Anyone. Get in the habit of saying hi or making small talk with strangers. Chat up the dry cleaners, checkout clerk at the grocery store, etc. It gets easier, especially once it sinks in that no one is going to flip out when approached by a nice looking lady.
In fact, you have the advantage by being an attractive female. You are the person least likely to be perceived as a creepy wierdo. Even women will be flattered by your attention.

Oh, and I should also add that it really doesn't matter what you say.
Back in my glory days I approached men I thought were cute all the time. I'm average-looking, but I never once was embarrassed for it. Once or twice a guy didn't seem very enthusiastic about talking to me, so I just said goodbye and walked away.
Usually I would try to find something about their appearance or what they were doing, and ask them an open-ended question about it. Didn't really matter if it was an intelligent question or not, you just have to start the coversation.

I've said really stupid things like "How did you get that dark tan?" or "Aren't you hot in that?" (double entendre, done right it goes over really well). Even better if it's a compliment question: "How do you get your calves in such great shape?". Then after they answer, you ask another question, such as "oh really, how did you like that place?" or "what did you think of xyz?".

"In fact, you have the advantage by being an attractive female. You are the person least likely to be perceived as a creepy wierdo."

That makes me want to become a creepy weirdo.

But, I have to also say that everything else Honey says is awesomely practical advice. You can do this, Anon!

Just don't forget to come back and tell us about it.

These are awesome and heck, if you had the nerve to do all of these things you are awesome as well! Excellent tips, I will follow them myself ;).

Hi Anon,

I am telling you that game is all Confidence. It sounds generic and cliche, but couldn't be farther from the truth.

I am quite social when I am out, and I talk to everybody about anything really. Honey's questions are very similar to what I ask guys and how I view/ approach them, it's good to be a tad cheeky and flirty and then NOT care what the outcome is.

I think that really is the key, not caring. The more you approach guys, the easier it will become.

If you feel like being flirty, do it. If you just want to go up and say hi, then do that too!

I always look at everyone I approach as a conversation. That's it. I don't think about a million things, or how I'm looking, or what they think of me. I try to get to know about them genuinely.

Obviously you keep the conversation light and fresh when you are first introducing yourself to someone. And then see where it goes from there.

Practice makes perfect too, so put yourself out there again and again and let us know how it all goes.

I guess I should have added that women and children are very unthreatening...
Robynne you're adorable, and also in the category of least likely to be perceived as a creepy wierdo too... Gosh I hope it didn't sound like I was implying that anyone unattractive is a creepy wierdo...
I just meant that for a man, being approached by a female, especially one that's attractive, is their ultimate wet dream. They're hoping that they're being approached because you're interested, so they're going to be responsive. Even if they're not interested, they will be flattered (and thus nice about it). Who wouldn't?

No, your advice was very clear -- I was just bein' goofy.

You're absolutely right that most men are flattered when a woman approaches them, and are generally very careful and polite if they have to turn her down because they're married or whatever.

And thanks for the sweet words. <3

You know what I've noticed more often than not?

When there aren't mixed signals of some kind it's easy to be more assertive. You and this guy have something great? Well, let it happen naturally, because great things tend to happen that way when it comes to matters of the heart.

But, if you're just both kind of dancing around the idea of it, then don't waste another second thinking about what could be. Don't narrow your focus and turn him into a fantasy, just enjoy his company and keep your eyes open for something that comes by and just FEELS right. You'll know it. I promise.

Thank you all for you advice!