Or rather where even to begin?

I have never flirted in my life and I am 29 already.

I can talk a bit to strangers but do not know how to shift mundane conversation towards something flirty and how to keep going... I just feel like I am too slow and whatever compliment crap that I may come up with I think looks fake... On one hand if I approach a girl in real life and tell her a compliment I think she may react more favorably than on the net for example because you know this is a real conversation and the odds for this to happen are more scarce, however I have no clue where to go from there...

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Now I also created this internet "hookup account" or whatever, where girls post their best pics and really not too much info about themselves... Even if I have the whole time in the world it is hard for me to come up with something that would not sound lame,,, honestly I feel like these internet accounts receive a lot of male attention and some of them probably really know how to talk to women hence I am not sure weather I have high chances to be replied to, I consider myself to be below average guy (of course I avoid opening up about that) ... So I think they get to choose from the best looking guys who talk the sweetest and I do not feel like I am on the top list... What I decided to do is to just message a bunch of girls and see what happens, but I do not really know what to say, what to ask, what to tell about myself or whatever, especially since the girls quite often do not provide a lot of initial info about themselves except for photos, so if I like how they look I tend to compliment their looks, but do they really dig it? Personally I like women beauty but I do not consider it the most important thing although it matters, in my opinion one way or another it only gets temporary importance- am really curious about getting to know girls more, I mean isn't it all about it? sure those photos are nice, but they aren't making me to know the person better...

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I was socially anxious for a big portion of my life so I never accumulated a lot of social experience, neither does it feel natural to me to tell someone compliments, even if I like them because I guess I am always afraid of judgement... maybe I misjudge the predicted people reaction by expecting them to react the way I would, I never liked compliments myself... but I am sure that need to change my ways of communication...