Should I try to shoot my shot?

Earlier a guy shared his story about shooting his shot at a grocery store. I've alway been adverse to the idea of this based on situations I witnessed when I worked in grocery stores.

There is an employee at the store I frequent that I have become enamored by. When I was job hunting I'd be at the store during her work hours frequently. Now our paths don't ever cross except for a one off stop I made a couple of days ago. I had honestly thought she moved on to another job.

Would me asking her out now be as questionable as I thought it was when I saw her almost every day?