Every time I am even remotely interested in a women, I pass on the opportunity to ask her out. How can I gain more self confidence and how do I ask someone out?

Hi everyone,

A bit about myself to give you all an idea of who I am:
I'm a 27 y/o male, single. I'm kind of a geek. I like video games, computers, reading, learning languages, and general nerdy stuff like that. I was never much of a sporty guy (although I do love watching hockey go habs go). In high school I was considered one of the nerds (don't know if this matters or not, but I'm putting it out there anyway). I guess I am average looking? Lol, I'm not a super model, but I know I'm not ugly.

My situation:

I've always been shy around women. I can strike up a conversation with them no problem, I have no problem speaking to them, they are humans after all, but every time I am remotely attracted to a woman, I don't ask her out. I can't seem to find the right words to express my attraction. Am I supposed to express my attraction to them?! Am I supposed to ask her out straight up? I feel like sometimes I'm not good enough to ask her out, I don't know why. I feel like I don't have self-confidence when it comes to pursuing women. For example, today I went to Ikea, there was a really cute girl at the cash, and we had a really nice conversation, I wanted to ask her out, but I couldn't muster up the courage to do so. I left the store feeling bad that I missed another opportunity to connect with someone I thought I had a connection with. This is just one example. Although, I have had success in the past with some women, they're few and far between. I think I'm afraid of rejection, but at the same time I know I shouldn't care if someone rejects me, life goes on.

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How do I ask a woman out on a date? Such a lame question, but it's one of the most difficult things in my life…

How can I tell a woman I LIKE her? That I find her attractive and wanna go out with her?

How do I do these things without being creepy?!

I am writing this today because I want to get over my shyness, hopefully meet someone, and have a fulfilling long-term relationship.

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Feel free to ask me any questions.
Thank you for your help.