@Tiger Hoods
Be direct, honest, and OPEN. You are playing your cards too close, being evasive, and being essentially misleading. You have to express interest first, then attraction, then some kind of intention. People severely overthink things. Timing is important. Reading the situation is too. My read is you are a little too in your head.
You have to be open, to open up a convo. You can gauge interest by how they respond. The parking lot approach? Harder in some ways, because they are going somewhere, and may be in a hurry, you don't know if they are just distracted and busy, or really not feeling you. Plus, strange guy approaching in parking lot, saying something about I know your from somewhere? What is she supposed to do with that?
In something like this, it's small things that serve as connectors. You are basically co workers, you know where she works, you know her hours, you know her co workers. Does she drink coffee? Does she wear expensive trainers? Start small, a lay up, not a three point shot.