I asked my crush at work out. She was a bit taken aback but with some, out of character persistance, she agreed to go out for a meal.
That was 8 years ago and 2 kids and 1 marriage later suggests it went OK. It was the best thing I ever did plucking up the courage to ask she who must be obeyed out. I've since reverted to my usual yellow streak down the back characteristic.
My concern at the time was losing a valued friend because I enjoyed her company. It couldn't have worked out better for me.