<human>: I don't have much knowledge of relationship stuff or dating. I've been in a long term relationship, the only one I've had, and it ended about 2 months ago. I've worked at the same place for nearly 6 years and have known this co-worker for about maybe 2 or 3 but we rarely ever chat. I always thought she was nice looking in a non-traditional way. Hard to explain but I like her. I chatted to her finally for about 15 minutes yesterday and she seems really nice(also no mention of a boyfriend). But I'm not sure how to ask her out. We've seen each other a ton at work, barely chatted until now, and there's a 5 year age gap. Am I reaching too far? I'm not even sure where to ask her out, I feel pretty lost here and even more so at my age but I've never really done this shit. 

We have dinner and drink nights out at work with some people, would that be an easy place to ask her out too? Like invite her to that? Or should I just go for it and ask for a more personal one?

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<bot>: Ended a LTR, not experianced in dating, but like a girl I've worked with for a long time and would like to ask her out. Any tips on doing it in a situation like that?