I'm 52, and I love my friends, but I have no wife or girlfriend at this point in my life. I haven't given up, but I've clearly seen that it's harder for some people to form intimate relationships than it is for others. On the other hand, I write stories and memoirs and novels, and many people can't do that, so there's compensation. You have to choose where to invest yourself, and make the best of it. I am really fond of my circle of friends, and I communicate with them often. It's an investment, and when they tell me about their day, and I discuss the memoir I am writing, it validates my sense of who I am. Schizoaffective disorder routinely beats the crap out of me, but I can have some sort of life, around it.

I'd say, talk with this woman you're interested in. Can't hurt. Rejection sucks, but you might talk her into a date. Who knows what could happen, but if you don't try you're guaranteed to get nowhere.