go for it.

My grandfather, with one kid heading to college, and another a junior in high school, married a 25 year old woman when he was about 47. They were happily married for nearly 40 years after (until his death).

The age difference is less relevant depending on the personalities involved, but I agree with kartek, its probably going to be on her mind, so id find a way to blatantly address it and put it to rest. Plus the fact that you were technically subordinate to her at work as well, not just a random guy, but a guy who used to work for her.

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