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Although I have seen it work, I suspect that it would be very difficult. I work with college age athletes and although I love the young people I work with I can’t imagine a relationship with someone their age. Upper 20s and 30s are years spent building a life and family. I’ve been there done that and would much rather listen and play with my grandchildren without the constant responsibility I once enjoyed. Physical attraction from old to young and maybe admiration/respect from young to old might make the idea appealing but maintaining a relationship is hard work and it helps to have empathy and understanding that comes from being in a similar stage of life I think. Sorry for the long answer.