You sound quite solid to Prudie, who did not deem the attraction you describe as being of the school-girl-crush variety. For you, 23 is a whole lot better, and more appropriate, than 43. It's also a sign of maturity that you say you're more interested in his personality than his looks. By all means, explore the possibility of a functional relationship once you graduate (assuming you will be 18 by that date). Prudie thinks you do, indeed, have something to be hopeful about.
A dear friend of mine (closest friend, actually) has been seeing a man on and off for about three years. The man is twice her age and has problems with alcoholism, drugs, and has serious maturity issues. She has admitted he is no good for her, but she keeps going back to him, saying, "I told him we don't have a future together; it's just for right now." I have told her in the past I was glad they broke up, so she knows how I feel about him, but since they last broke up, they have been "hanging out." She says she is over him but still tries to be a good friend because of "all he's going through right now." How do I go about gently and nonjudgmentally telling her I am not comfortable going out with them when I am invited? I don't trust the guy and definitely don't feel safe around him. I want her to be able to lean on me for support, but as her closest friend, I feel I need to be honest with her, too. Please advise.
A woman who breaks up with a walking catastrophe and then "hangs out" with him has a bolt loose, ergo, you might as well save your breath for blowing on your soup. Anyone who renounces, then returns to a relationship with an immature, drug-addicted alcoholic is far down the path of self-destructiveness. Prudie gives you her permission to forget about trying to be gentle and nonjudgmental. If you actually fear for your safety, simply tell your good friend that you don't feel safe around "Mr. Right, for now" and therefore you will only be able to offer support and friendship when it's just the two of you. You can't get much more honest than that.