DON'T GO TO BARS. You will never be able to compete with dudes that can buy more drinks or showed up there in a better car than you. This may sound sarcastic, it isn't. It is pure experience. I can't tell you how many times I have overheard a woman I just bought a drink make fun of me to her friend about how they won't have to buy a drink while I'm around and at the same time lament they have no personal interest in me. All when they thought I was out of earshot.
I would suggest going a local community group you are interested in or would like to try. I do not recommend you join the local Star Wars re-enactement group. Chicks (generally) don't like Star Wars and find guys that do to be dorks; and shortly find yourself in a sausage fest. If there is a chick there she already has 30 others there to choose from and you are essentially back in the bar where what kind of car you drive matters.
I recommend something like a SCUBA group. If you have never done it but wanted to: 1. you get to participate in something you wanted to do, 2. If you talk to a woman while there you have something to talk about besides whether or not Han shot at Greedo first, 3. At least you get to see them in their swimsuit (basically their underwear) before they reject you. Focus on SCUBA jokes like "Why did the chicken cross the road...I like SCUBA and think you are hot in your Bikini and like seeing breathing apparatus shoved in your mouth." When she pretends to to get "offended" and acts upset, listen in to the background. If you hear a woman laugh because of the boldness, GO TALK TO HER. She has a sense of humor and is halfway there. Tell here her the one piece she is wearing is nice but it is driving you wild to see her in a bikini. If she shows up next session in one. you are gold. No need to play it cool. Be yourself and ask her to a fancy dinner at Red Lobster.
I don't know why chicks think the Red Lobster is fancy. I think they suck. But if they like it they just might as well, har, har, har...
Yes I am a sexist pig.
Really though, try new activity groups, not bars. Focus on the activity in conversation with them and let the humor about the activity flow. It takes pressure off thrying to make ackward conversation. Make sure it is an activity you are OK with. Preferably woman can traditionally get into. Still be prepared for rejection. I have known women to initially reject me because I seem tense. After the rejection I keep a positive attitude in the new activity I enjoy regardless of them. After a while they get to understand me and start throwing hints that they would like me to ask them again. Even if they don't, there are new woman that will come in to that activity. Of course the "older ones feel a responsibility to warn." This is where the real fun begins!!!
I let them, why? Because if there is an old chick upset when a new chick shows up and shows interest in me I can claim the old is jealous. It is not not a lie. Not true, but not a lie. I phrase it like this; she claims to not want me but she makes a point to explain it to you, a stranger.... "you are a smart human being right?" She always says yes. (nobody likes to admit they aren't) "why do you think she is making a big deal about me?" and immediately hates the "old" one and assume she is psycho. But at the same time they can't let go of the fact a woman cares so much to warn. As a result they wonder why, even though you haven't mentioned the word "lightsaber" once. If the new one asks for details, just say "decorum" prevents you from talking about it. It's a big word that sounds smart. She'll draw her own conclusions. In fact at some time ask the old that rejected you, if you could just be friends. By doing so, when you tell the new you asked for that, she will ask for it from the old. The old will acknowledge out of honesty. She will a "but, but, but." However by then she might as well be asking her out for you.
Rinse, repeat, loot...
Of course by then I can't see them because I am making regular trips to Las Vegas to bang hookers, play poker, and test the limit of my liver.
What was I talking about, oh yeahhh! Who hear is over 18, is willing to pay her own expense to come see me, a female, hot (I like nerdy girls), and doesn't mind I live in my mom's garage?
Edit: or alcohol induced poor spelling and grammer?