I'm of the camp go for it, the worst that can happen is she says no and you are no worse off than you are now. When my Mom was a young nursing student in the early 50s, she took her drivng test and failed ...2 times with the same jerk Pa Trooper, after she passed the 3rd time, he asked her out and believe it or not she said sure. (I NEVER would have gone out with a guy that flunked me once let alone twice) anyway 5 years after they were married I was born and in 2005 we celebrated their 50th anniversary.
So I say go for it.
So I say go for it.