Dear Prudence

Long-Distance Gender-Bender

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Dear Prudie,
I was having a long-distance relationship for about nine months … but I had never met this “guy.” A mutual friend hooked us up, but she, as well, had never met him. Anyway, one day while we were talking, my “guy” said there was something I needed to know. It was that “he” was really a she! I was in shock at first, and then furious. This person had sounded like a guy the whole time. I was in love with what I thought was a him. Before this I think I was attracted to women, but maybe only out of curiosity, so I thought that I could work with it. I still love this person but ask myself everyday if she really loves me. I think maybe not—because of this huge lie she was telling me for nine months. She wants to come see me, but I am scared and nervous and unsure if I should go on with this relationship any longer.

—Really Confused

Dear Real,
What do you have to lose? If you are able to separate personality from gender, give it a shot. Probably the reason your corresponding “boyfriend” didn’t fess up is that she imagined this information might queer the deal, no pun intended. What is unknown at this point is if this person is a butch lesbian or perhaps even considering a sex change. Given that you say you’ve had some curiosity about same-sex alliances, invite her to come visit and see what happens. If things go well in person, it would be a hell of a “how we met” story.

—Prudie, explorationally

Dear Prudence,
Her name is Amy, and we are co-workers. It is safe to say that I am infatuated with her. We have a very friendly co-worker relationship, we take cigarette breaks together, we talk about life outside of work, and we joke around quite a bit. I have been flirting with her obviously for a few months now. She has never taken offense to my flirtations and has always responded to them with a laugh and a smile. Recently, I have noticed that she has been flirting with me as well. I really want to ask Amy on a date sometime, but I am very scared. Here are several reasons why I am scared: For starters, Amy is older than I am.  She is also married. I have met her husband on two separate occasions, after which I was flooded with guilt. I really have a crush on her, but I do not want to ruin the very good (and proper) co-worker relationship that we have. Just seeing her drives me crazy with infatuation, and seeing her husband drives me crazy with envy. I believe that if I made some kind of move (asked her on a date, kissed her, etc.) there is a 70 percent chance that she would accept my offer. I know it is wrong to “put the moves on” a married woman, but I think there’s a good possibility she would have an affair with me.

—Scared and Guilty

Dear Scare,
Yoo hoo … this girl is married. And according to Robert’s Rules of Order, this fact removes her from the class of people we ask out on dates. You are playing with fire on this one. And don’t make too much of the fact that she offers you a laugh and a smile without taking offense. Some women do not believe in cutting guys off at the knees, and she sounds like one of them. Accept your attraction as the crush that it is, and try to reduce contact. For all we know, this may save you from a duel, an alienation of affection suit, or a harassment charge.

—Prudie, prudently

Dear Prudence,
I have been with my steady boyfriend for three years. We’re both going to be graduating college soon. From the beginning his parents (mainly his mother) made it clear that they weren’t happy about his dating me. Most of this dislike is admittedly (on their part) from rumors they’d heard about me, none of which were true. I tried to be polite and friendly when we would run into them in public, but they would ignore me and pretend I wasn’t even there. His mother even said if I ever came over to the house, she’d leave. I found this behavior beyond rude, and despite their son asking them to at least be polite to me, they have continued this behavior. We have managed to keep our relationship completely separate from his family (my family loves him), and we’re really very happy together. The problem is that now (after three years) they realize I might actually be sticking around in his life, so they’ve decided to start inviting me to parties at their house—though never to my face, only through their son. Am I supposed to just forgive and forget? They were as nasty as could be to me for three years, and now they realize it has distanced their son, so they’re trying to be nice. I don’t even believe their intentions are to get to know ME, but to stop alienating their son. Am I being selfish by not wanting to deal with them?


Dear Frus,
You are not being selfish; you are being shortsighted. Your feelings are perfectly understandable, by the way, but they are not strategic. Prudie has some ideas for you—and they do not involve forgiving or forgetting. They involve poker, and right now you’re holding a straight flush. If you choose to “pay back” the beloved’s parents, particularly the mother, what you will get is continued frost and discomfort. If you fashion yourself as the gracious winner, however, you will have control of the situation. (And you will make his mother nuts.) A bonus point is that your beau will be most grateful … and you will have bathed yourself in the light of magnanimity. You will appear forgiving while in reality you will be holding all the cards. P.S.: There is no need for you to discuss the reasons for your new approach. It can just be a secret between you and Prudie.

—Prudie, tactically

Dear Prudie,
I frequently e-mail a male American friend of mine who is working overseas. We have been friends for years, since we were both high-school freshmen (eight years ago), and he has continued to ask me out every now and then over the years. I have always been uninterested in that kind of relationship with him (and have always politely declined). He has told me that he understands and that the friendship with me is of utmost importance to him. We haven’t seen each other in years but have kept up close contact through phone calls, e-mail, letters, packages, etc. We feel like family to each other now. However, I’ve been beginning to find that I am finally falling for him romantically, but after all of my rejections of his “advances,” I’m afraid that he would not want to try again with me. If he did, this time I wouldn’t reject him, but I’m afraid it’s too late for such a hope. It’s also difficult to bat your eyelashes at a guy via correspondence. I fear that my negative responses over the years may have ruined a possible perfect match. What should I do? Help!

—Girl Who Cried Wolf

Dear Girl,
Prudie will now give you the electronic equivalent of eyelash-batting: E-mail or write your friend of long standing and say that you find your feelings moving into the realm of the romantic. There is strong precedent, by the way, for this kind of sea change in a relationship. Prudie’s own dear mother has a saying that captures it perfectly: “Love is friendship that has caught fire.” Morphing the platonic into the romantic can offer a very strong foundation for a partnership. Prudie’s guess is that all you have to say is that you find yourself seeing him differently, and he will do the rest.

—Prudie, romantically