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?