The number one thing to keep in mind is that at least some women you are interested in will say no, and possibly for a really good reason like they could already be committed to someone else! It's pretty much a no then with what they are telling you in a nice way.
It really just comes from being straight-up bold like asking them for a dance in person. Who cares with being turned down? It happens, and I even felt like my ego was crushed about being turned down by hot women over a simple act of taking photos of them posing together. It was crazy, so I felt bad and didn't like it. It was still good though and all in the name of fun, so who cares.
I guess the number one rule for me when it comes to playing the dating game is not to be so outcome dependent about anything. All these strategies and books on picking up certain women is rather funny, but the truth is that we need to hear the full story with any questions we have from a really experienced girl. Meet so-and-so, she's a dating coach and giving away her tips for free because she wants the world to have more kind of guys she approves of dating women they want to be with! I finally found someone cool like that and she's local while having been able to answer all of my questions. Well, if you do one-on-one sessions she's going to charge but for group settings like the one I went to, she was cool about answering my questions with no filters. It was very helpful, so now I just don't really care about being rejected and don't mind staying nice about it while remaining upfront and confident with the ladies I like.
Well technically, my asexual girlfriend and I are not together so I can practice what I learned in these classes by just asking her out. She's like a good sister to me though, but I still really like her so if she said no to me, it's not like she won't ever talk to me again and avoid me. She's actually my best pal out of all the girls I know. I think she's safe to practice my dating moves on.