This thread, except for the diversion into The Villages activities, is very interesting to me. I am 71 years old. I have had two marriages, with 11 years of being single in between. During that 11 year interval, I dated one man on and off for the first year (it ended because he wanted to get married and I knew that would be a mistake), and for almost all of the ten years following, I didn't date or want to. Being an introvert, I was absolutely content to live on my own, free to do as I pleased, kids leaving the nest, pursuing my career, owned my own home, and was in control of my own money. For many reasons, I had no intention of ever marrying again.
And then things changed. DH and I worked for the same company. We were friends and colleagues for several years before he was widowed suddenly, so we already liked and knew each other very well. When we carefully started dating, we both knew right away that it was going to lead to more. If either of us still had children living at home or if DH had a problematic ex-wife, I never would have considered it - I don't tolerate drama at all and after raising my own children, I didn't want to raise someone else's. Our incomes and financial obligations and goals were roughly the same. We have been such a good fit for each other and are coming up on our 22nd anniversary - longer than either of us were married to our first spouses. Our life together is satisfying and happy.
That being said, if I find myself single, there is no way in hell that I would ever marry again. Don't get me wrong, I love being married to DH and would be grief-stricken to lose him. However, I have no interest in being married to anyone else, I would be quite comfortable to be on my own again, content with my memories. Some women are lost without the emotional connection, need to be part of a couple, but not me. As I tell DH, it's too much work to train someone new.
As far as having someone to assist me in my old age, I have 3 children, all 3 have told me that I have a home with them if I ever need it (although that would be a last choice for me). The eldest is an internal medicine doctor, so medical guidance and care is kind of a given.