Are nice guys destined to finish last? I am a 50-year-old, never-married, child-free, employed nondrinker. I’m still single, because the women I’m usually interested in are either married, young enough to be my daughter or have complications. Recently, I met a 40-year-old, twice divorced, recovering alcoholic with three kids who has served time for DUI. The men before me physically abused her. She is usually attracted to men with shaved heads and tattoos who ride Harleys and own pickup trucks. I’m squeaky-clean-cut, dress in coat and tie, conduct myself as a gentleman and prefer sedans. She still has strong feelings for the last guy who beat her, even though she has a restraining order against him. She says that I’m caring, loving, attentive and helpful, but she is starting to back away, saying she’s tired or busy. I’ve done all the right things, but I’m made to feel as though it’s not enough. This has happened before. What am I doing wrong?

You’re dating a woman who is attracted to the same kind of person you are: unavailable for a healthy, loving relationship. She is infatuated with, and dates, herself: the addict-rebel-scofflaw who communicates indirectly and manages anger poorly. A woman like this finds you charming, initially, but since she really doesn’t want to be rescued, she backs away physically and shuts down emotionally to break off contact with you. If she were more emotionally awake, she would simply tell you it was over. If she were more spiritually mature, she would be more devoted to healing her issues because she wants less drama in her life.

You may be a clean-cut Clark Kent type on the outside, but that doesn’t fool me. Internally, you’re a Dark Knight, wondering whether to fight against your natural tendencies or to give in. Usually, you surrender to your addiction to women who can’t return your sustained interest, who are profoundly emotionally wounded, whose social position (married, too young, struggling with addictions and affection for abusers) means that a relationship with her would make you a social rebel. That’s not wrong, it’s just not in your best interest.

Choosing a partner who is emotionally unavailable is very revealing. It says that an intimate relationship is not what you are really after. What you want is to win. If you can persuade a woman who would not typically be attracted to you to fall forever in love, you will have proven your worth. There is a part of you, perhaps the young boy who didn’t get enough of Mama’s attention, who yearns to enter the arena and fight. Your question (“Do nice guys finish last?”) signals the presence of that competition (Who did you compete against for your mama’s attention?). At 50, you’re entering the second half of life. Why not grow into the man who enjoys a reciprocal relationship, rather than one who tries to sell a woman on loving him?

I have been separated from my wife for six months, and the divorce proceedings are going along fine. My problem is that I am obsessing about my regrets. I keep thinking about the girls I dated in high school and wonder if I should contact them. What do you think?

It’s incredibly common to want to walk backward when life didn’t turn out as expected. But you are not an adolescent anymore (hopefully!), so you can’t really go back. Reconnecting with old friends is fine, but be certain to live in the present with a vision of the future. And drop contact with any old flame if you learn she is married. You don’t want to contribute to another divorce.