Most of success has come from 'natural' interactions with women. By natural, I mean through another friend, school, work, etc. We were both in the same situation with the same purpose, so it just makes it very easy to go for it, regardless of the risk of rejection.

However, I want to be able to approach women that I think are beautiful, even though I don't have a reason to. It feels very awkward and strange to me. I have no problem asking strangers for directions, help, or start a conversation. But I cannot treat a cold approach the same way, which is really frustrating to me.

What are some tricks to getting over this?

I was particularly frustrated during this past spring break because I wasn't able to land anyone from the beach. Even after casually playing catch with girls I didn't know, I still wasn't able to succeed or naturally transition. I did have success at the bar though, which adds to the frustration lol.