[Keaton421]

I think if she accepts a night on the town, that's a good first step. If y'all enjoy it, ask her out again. Make it clear this isn't just a work relationship, if you can. Get yourselves good and drunk and pry a bit on the boyfriend deal. If she starts flirting with you before that, even better.

Does she know that you know that she has a boyfriend? If not, act like you didn't know, and tell her it's just a few drinks or dinner. The point is to get closer and bring your relationship out of the office which is a sad, stagnant place.

Older women? No big deal. If you were 20 and she was 40, she might be craving a young buck, but that's another story...

Foreigner? Shouldn't be a problem - Japanese people get tired of the same East Asian faces day in and day out. Do y'all speak the same language?

My advice is, just do it. Ask her out. You won't know what happens until you try. And you definitely don't want to spend the rest of your life wondering "what if..."