Undestand what it is youre afraid of.
Most guys think they're afraid of rejection but this is not true. Example , imagine you could hit on a subordinate at work. In that situation she would not be able to reject ypou and would have to come along even though for her it might be horribly akward and unpleasant.
Would you hit on her then?
I know I couldn't .
See youre really afraid of making the girl feel akward. What you should do is approach in a way where you take all the social risks yourself, you go away smooth;y if she rejects you and you don't make her feel uncomfortable. Imagine you're at a bar , and a MILF-ish looking older woman comes up to you.
She's successful , she's confident but just not your type. You talk with her , hint you aren't interested , she wishes you a good eveening and goes back to her chainsmoking friends.
How did that experience make you feel? It was a genuine compliment , that would have made you feel like a guy who is *so* money that girls want to meet and blag on him.
Right.
When you CA , you are paying that exact compliment to a girl.
You are doing her a favour. So get out and do that favour !