Hey, Josh.
I'll offer you a critique of the first one:
First, I'd either get her chin down or the camera up. You can see what I mean when you compare this one to your second view. See how we're looking up on the bottom of her brow, nose and chin? Notice what this angle has done to her chin-line.
And just as important, the lighting is very flat. There is no definition of shape and texture, and no separation of the subject from the background.
Long sleeves would have helped. Take you hand and cover the bare arm. Can you see how much attention it draws? Maybe a bit of vignetting at the bottom of the image will help.
The setting is pretty shallow. Moving her away from the background, even a few feet, will make a nice improvement.
Finally, this would benefit from a longer focal length. This looks to me like a normal lens was used, which is a bit too short when working in this close. It looks fine in the second image.
Nice location and good expressions!
-Pete