I've had a few cis-male and MtF friends ask me this kind of question, so I've given it some thought for a long while already. In summary:
I think for me it was definitely overcoming my insecurities. Once I felt confident about who I was, what I wanted in a partner and why, confident that I needed NOT ANY APROVAL from anyone ever, and could be myself and do what myself wants to do instead of what mommy or society tells you just because that how it is MEANT TO BE (as long as you don't hurt anyone of course), suddenly all the relating and flirting kind of came in a natural, fun way. The constant fears and insecurities about if doing so or so was OK in a date or or to get a date were actually dragging everything down but then started to go away.
I think most genetic male are led to believe by society or family that you need to get the girl to approve of you -and of course you have to in at least some way in order to not be a rapist-, that you have to sort of convince her or proof her that you are the right material, but to do so I think it is key to not worry about "asking her out" or "if she likes me or not" and instead just focus on enjoying yourself, be happy and have a good time, not kiss up and tolerate irrespectful behavior THEN everything will click naturally. I really think the assumptions behind this whole concept of "asking her out" really send you in the wrong direction, in a direction of neediness and needing approval, which is quite the turn off, instead of the direction of feeling right, having fun, and finding people who want to also have fun and feel alright with you. And I do not mean "fun" as in a one night stand or something, but long lasting "fun" and comfort with your partner in your daily life.
I think this whole asking her out thing has to become a no big deal, fun, casual thing focused in having a good time (instead of being fearful about getting turned down or judged wrongly) in order for it to work consistently. I could not repeat enough how so many genetic male are somehow lead to feel fearful and nervous about dating and asking her out for so many years while they grow up and later on in their lives. It just builds up anxiety and neediness, whereas it should just be a casual, fun thing, because relationships are in good part about constant mutual positive feeling. That will not happen (or with difficulty) when you are getting dragged down again and again by your fears and having second thoughts about you relating with *that* person. It is hard or nearly impossible to be an attractive person when your mind is full of second thoughts and fears. When you are having fun and feeling right about yourself it is just magnetic to other people.
You cannot obviously start feeling secure and get rid of all your doubts at once, but I think one can take baby steps towards that, and find out that you know, whatever happens it will be ok, and you just learn from your mistakes. For me I kind of had to get out and do them just get to feel that it will be ok anyway, sooner or later you get some sense of self and confidence and get a hang about it. You cannot do that and learn and get over yourself by "closing up" to opportunities like maybe talking to someone who looks nice out there or going out to some social gathering due to fear of getting turned down by someone you like. And when you do so, you have to genuinely feel that it is alright, that it is your right to do any of those things, and that the important thing is not wether it works or not, but for you to have fun and feel alright! So go have fun I say, then eventually things will turn your way!
Never had some abusive jerk to whom one of your female friends or a relative was deeply attracted? Am NEVER in for being a jerk because that is just wrong, but you can see that the jerk is focused about good feelings, having fun and doing whatever feels right to his twisted point of view, and never looks for approval or needs it. And he gets tons of dates.
