So what's my next play

Asking "new" women out has never been a strong point of mine. I've always been acquainted with them to some degree before whether it be through friends of friends or work relationships or what not. Recently I have been flirting with an attractive girl that works the front desk at the gym. I've introduced myself and we've chatted a handful of times but mostly about silly stuff like the weather being crazy and what not. She seems friendly and I'd like to ask her out but am not sure where to really go from here. She seems friendly and I don't know if she's flirting back with me, just pleasant in general, or is just doing good customer service.

Should I continue to chat her up about more personal stuff to gauge if she might be interested? Should I fish or straight out ask if she is seeing anyone? Or Should I just openly ask her out and take the rejection in stride if she was just being nice?

If you are interested, then ask her out straight away with the understanding that she may say no. Her saying no isn't the worst thing in the world, and you can play it off as "giving it a shot" and go back to being friendly with her. Don't make too much out of the whole situation, don't stress about it, don't overthink it, etc.

Good luck.

Do not ask her out fella. If she works in a gym shes probably a looker. Maybe shes nice to all customers as part of her job. This is what you must find out. Does she show the same attention to others?
My way in here would be to casually drop in the conversation that you have recently split from a gf and taking your frustration out at the gym etc, all that sort of pish. This gives her the opportunity to tell you about her current relationship status and will let you know if she wishes your little chats to get to a more personal level.

The last thing you want to do is make a twat of yourself if she was just bing nice as part of her job. So in summary, bluntness in this situation could be fatal for your chances, some gals need approaching from a more discreet angle. good luck

I don't think you should try to open with a line about your recent breakup. I also don't think bluntness is going to be fatal to you. It will just bring about the inevitable more quickly. If she likes you, she'll say yes, right then. If she doesn't, she'll say no, right then.

Grow some balls and ask her out.....just be done with it. It's tough getting a date when a girl works in the service industry.....she probably gets asked out a lot, but hey you don't go anywhere not asking....it won't kill ya.