One of the reasons so many guys have a hard time getting dates is that they don't have the confidence to ask a girl out. Timid guys tend to let their fear of rejection overrule their desire for romance. Many shy types want women to make the first move, which happens sometimes, but it's not something a guy should count on. Besides, no woman wants a boyfriend who can't muster the courage to even ask her out.
There are ways to ask a girl out with minimal risk of rejection. You just have to know how. So, I present to you: A Coward's Guide to Asking a Woman Out.
Choose your target wisely
Your first challenge is meeting a woman. You're probably not the kind of man who is capable of walking into a bar and chatting up a woman. What you need to do is attend professional networking events, work-related happy hours, seminars, tweet ups and such. If you don't have the sort of job or profession that holds those types of events, get involved in a charity or take up a hobby that does. I'd recommend going to social media events as an interested observer. They are crawling with women -- many of whom don't know when to quit drinking.
You'll have an obvious pretense for striking up a conversation, and you're expected to interact with people -- it will look weird if you don't. Bring business cards.
Ask a lot of questions
Everyone likes to talk about themselves, but especially girls who are drinking. Keep the first part of the conversation light and professional, and keep bringing it back to her. Remember to find whatever she is saying very helpful and interesting.
Find common ground
You'll have to transition the conversation into more personal stuff but nothing too heavy. Your real interests don't matter. You may even need to make something up about being into girl stuff. Some examples: You are an avid wine enthusiast, a hard-core foodie, you love the television shows Girls on HBO, and "The Real Housewives of Somewhere." This might require research. Don't lie unless you've done your homework.
Make your move
If you keep the conversation going too long, you're likely to say something stupid or off-putting. I know how you get. Make up a reason to contact her again, and make sure to get her e-mail address and her business card. Then tell her you're going to the bar, and ask if she wants anything. Tell her it's your treat, as payment for the advice, support, guidance or whatever she has been blathering on about. (Remember, if she says no, it's not rejection. You asked to buy her a drink as a way of paying her back.)
To sum up ...
In case you missed the subtlety of this exercise, you approached a woman, talked to her and asked to buy her a drink. If she accepts, you can go back and continue the conversation. If she doesn't, well, it's a mingling event. Cast a wide net. Before you let her go, try and plan something under the auspices of an informal meeting. Since you're such a big foodie, you know a great restaurant (more homework) with a fantastic wine list. Remember, you can't do Sundays, because that's when whatever show women like comes on.
Of course, the much easier thing to do would be to grow a pair. But that might never happen. So play the long game. Keep trying to meet under false pretenses, until she either enjoys your company or stops returning your calls and e-mails. The worst thing that can happen, besides a restraining order, is that you will have made a friend who could potentially set you up with one of her timid friends.
If this doesn't work for you, just computer date. You don't need game for that.