good job man you did the necessary first steps to solve your problem, you gotta keep going at it. this may or may not take many attempts, so dont get discouraged. getting 1 number in 2 tries is actually decent. also you did it, which is a success in and of itself. you are now able to take action towards your goal.
you get more practice and it becomes less awkward eventually. its still kinda awkward often times. you need to learn how to have fun while doing this, because if you only see it from the perspective where you want something to happen and it doesnt, you will get very frustrated. so very much like the therapy this is about changing your way of thinking while you act. the good thing is that there is actually a biological program that runs when you interact with the other gender so you dont really have to learn how to be flirty, its more like allowing it to happen.
personally, while i had some experience earlier in life, i found my first gf at 32 (im now 34). took a lot of effort on my part, much more than just asking for a number twice.
it can be easier than that, but i really wanted to make it happen after missing out many, many times. it was well worth it, for multiple reasons.