Zach you can rationalise why you shouldn't do any approaches as much as you like, or you can just decide that it's a fun game you're gonna play and start trying to improve at it. You say you're opening is fine, but you're not opening because you don't know how to transition. Well, just start opening first until you're totally comfortable with it, and then work on transitioning.
You're basically saying "well I have this video game but I don't want to put it in the machine because I can do level one, but I can never reach the end of level 2 so why even bother?" Well you play the levels over again until you beat them, and then you move on to the next levels and pretty soon you can stick it on a harder setting and play through 1-5 no problem. Also, you HAVE FUN doing it and it feels good having a challenge and then pushing through it!
As a final transitioning tip, why not try doing a quick cold read, or just notice something about her, and then after that discussion if no new threads open, then just starting a DHV story just for the hell of it and seeing where that goes.
For example
PUA: Hey do you know where a cafe is?
Her: Yeah there's one just over there on the left
PUA: Oh cool, thanks. Oh hey that necklace is really chic - where'd you get it?
Her: Thanks

Ya I got it at H&M on sale actually blah...
PUA: Something about H&M / shopping with a friend recently / ANYFUCKINTHING
Will this kill you? No. Now go out there and start doing approaches. The only failure is to NOT try.