How do you approach women? What works and what does not? When can you tell a women is open to be approached?

It's sad to say but I'm 26 and never approached a women. For some reason I can not do it. Any tips? I think knowing I will get rejected most of the time like most men will hurt me. I'm the type of person that is very hard on himself and getting rejected a lot may really screw me up mentally. I've done online dating with success but I'm not into women that are larger than me, fitness and staying in shape is important for me because I keep in great shape. Or the women online are very clingy and desperate, help!!!
How do you approach women? What works and what does not? When can you tell a women is open to be approached?
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