Dude in 5 nights in Austin I got 5 numbers, 4 tonguedowns, and two options to go home with on Valentines night... you have more l33t PUA sk1llz than me, but factor in the Brit TALLY HO element and we should come out even.
Just go out, and stop waiting for Tyler to give you permission to talk to a girl.
It sounds like you haven't really set your mind to most of these goals... going Raw was not on the list, but you achieved that, so that's really what you set your mind to.