Dear Prudence

Dad Looks Like a Lady  

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Dear Pru,
I wear dresses, nylons, pantyhose, and high-heeled shoes, but I do not desire to look like a woman. I am totally heterosexual and have a monogamous relationship with my wife. I wish to dress like this 10 hours a day, every day. My wife is leaving it up to me to come out of the closet and tell everyone, and she is very supportive. She surprises me by buying skirts, dresses, nylons, pantyhose, and high heels for us. Should I come out to my children–16 and 12 years old–or wait until they are, say, 18 years old?

—High-Heeled Henry

Dear High,
If you are living with your family, chances are pretty good that the kids have already put two and two together … that is, two sets of high heels, etc. On the off chance that they do not know of your fondness for frillies, it might be easier for them if you could put the news on ice for as long as possible. This is just a guess, but Prudie does not think your wish to play dress-up 10 hours a day is going to work well with your work life, though you do not say what you do for a living. Prudie thinks it’s great, by the way, that your wife is supportive of your feminine side. If Prudie’s beloved showed up in a skirt and pumps, she would probably wind up in a dead faint, but that’s what makes horse races, no?

—Prudie, assentingly

Dear Prudence,
I am a divorced woman, age 44. I have been divorced for two years. I was married for over 20 years to a man who paid no attention to me unless I happened to walk in front of the TV set. I have a man in my life now whom I love very much. He is a caring, affectionate, romantic person who makes me feel very special. We have been seeing each other for one year. We have even discussed marriage. My problem is that he’s a little rough around the edges. At first it was troublesome. For example, he doesn’t mix well with my company’s execs at cocktail parties; my brother asked me if he owned a suit; one of my friends said he looks too much older than me. You name it Pru, everyone had an opinion. When we’re together at home or at the park with my dog or the movies or dinner, I feel just wonderful with him. Mix him with my family or my co-workers, and I am squirming, just waiting for him to say the wrong thing or for someone to raise their eyebrows because he didn’t know which wine to order with fish. This man is so good to me. He is a wonderful lover and is always showering me with thoughtful gifts and cards. My boss says never be with a man who could embarrass you in a social setting. What say you, Pru?

—Lost in Love

Dear Lost,
This one seems kind of simple. You only need to decide where you “live.” Is it at executive cocktail parties or in your private life? Prudie is guessing that any woman who’s had a clinker marriage would gently push you toward a guy with whom you “feel just wonderful” and who’s “a wonderful lover and is always showering (you) with thoughtful gifts and cards.” Edges can be smoothed, cupcake, and wine choices are why we have sommeliers. Your boss, by the way, sounds like a real student of human relations.

—Prudie, encouragingly

Dear Prudence,
I have been dating a wonderful man for five months, but my parents despise him. He’s not perfect, and I’m not looking for perfect. My parents, particularly my mother, feel he is not good enough for me. They feel he is not at the same “social level” as I am. He has a steady job as a tradesman and is very hard-working. He is kind and respectful toward my parents. My mother feels that he is not good enough because he doesn’t have a college degree. I will be graduating from college this year, and my parents are extremely upset that I am in love with a person of a “lower station.” They say they haven’t spent all this money on my education so that I will marry a “laborer.” Because I am a full-time student and I do not make enough money with my part-time job to live on my own, I live with my parents. Every time I come home after a date with him, we have the same argument over and over. I should not be dating a tradesman; I should be dating someone with a degree. It hurts me when they say cruel things about him and his occupation, and I’ve told them how much it hurts me. What do I do? I am tired of arguing.

—Frustrated Beyond Belief

Dear Frus,
You and the writer of the previous letter ought to form a support group, and then perhaps introduce your parents to her boss. What is it with these upwardly mobile people who are so into superficial values and appearances? Too bad your parents are not well-traveled enough to know there are lots of degreed SOBs cruising around and that some of the people of your “same station” are miserable human beings. Looking down their noses at your “tradesman” is nothing you can change, but in order to lower the temperature of the disagreement, you might tell them that Jesus was a carpenter, you will certainly be on the lookout for an MBA, and right now you are focused on your education. In other words, play down the romantic angle, bide your time until you can live on your own, and then have a wonderful life with your fella.

—Prudie, groundedly

Dear Prudence,
I have been seeing a guy for about four years. He has secrets about himself that I am having trouble accepting. I cannot get answers from him, and his friends of many years say they don’t even know the answers. He keeps his place of residence a secret and almost everything about his personal life, too. He’s said he has a son, was divorced, and his ex-wife died. He stays with me two nights a week, and I see him every day except two days a week. I am sure he does not tell me the truth about what he does these nights. He will not see me at all for any reason on these two nights. How do I find the answers to these secrets? I want to know for my own peace of mind.


Dear Won,
It is possible that you could find the answers you’re looking for with the services of a private investigator. You might ask yourself, though, before you make that kind of expenditure, what, exactly, your life would be like with a man who is so secretive and who very likely has something to hide.

—Prudie, tellingly