Nice picture. My only problem is with the wink. It didn't look quite right and now I know why. When a person winks, the cheek on the closed-eye side scrunches up when that eye closes. That was not shown in the drawing. Minor, but something to keep in mind in the future. Look in a mirror and wink. Other than that nice picture.
Ain't it funny how the quiet and/or nerdy ones always seem to be the most awesome late-bloomers?
Nice job, man! Aside from the obvious, your anatomy is quite realistic and I really like the shading and coloring on this. I also think you did a pretty damn good job of translating her from pony to human, some artists seem to stumble on that part. But anyways, great work!