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Dear Prudence,

I have a friend, Kathryn, who is a post-op transsexual (she was once a he) and appears by most standards as an attractive female. However, Kathryn is currently dating a man who does not know about her past. (She told me she'll tell him when she's sure he loves her.) Fred is a nice straight man who I think should've known about Kate's secret a few months ago. Kate is an old friend (from high school) whom I stuck by through all the trials and pain she endured. Now I feel like an accomplice to a huge lie. Do I tell Fred? Do I wait for Kate? It's a strange problem, and I have no one to ask. HELP!!

—Questioning Friend

Dear Quest,

"M. Butterfly" and a few details notwithstanding, Straight Fred will most likely discover "the secret" on his own. And you are in no way an accomplice unless the three of you are, um, in love. You have no standing in this matter, as it were. Kate may learn, the hard way, that "forgetting" a gender change is not in the same category as omitting the fact that one had a brief, annulled marriage, for example. Unfortunate reality: If you, Kate, and Fred are all in the same town where you two "girls" went to high school, the secret is a cherry bomb waiting to explode. It has been Prudie's experience that you can warn a friend once, maybe twice, and then you must step back.

—Prudie, historically

Dear Prudence,

A co-worker with whom I am good friends confided to me that she is keeping company with a 16-year-old boy. Today she admitted she could "get arrested" for what the two of them do when they spend time together. My friend is a single, divorced mother of two young children (ages 4 and 9). I am greatly disturbed that she is behaving this way. It could have serious consequences, not only for the teenager but for her and her children. She showed me a picture that featured her 9-year-old son with the teenage boy. Do you have any advice for me as to how to handle this situation? I do not know the teenager, not even his name (she refers to him only by a nickname), so there is no way for me to contact his parents even if I wanted to intervene. I have reminded her that her interest in him is a dangerous game that could result in her incarceration and the loss of her children. That doesn't seem to faze her. My instinct is to stay out of it. After all, we're just co-workers who share girl talk over lunch, but the fact that what she's doing is illegal (not to mention harmful to more than one person) greatly concerns me.

—Confounded

Dear Con,

Prudie wonders if your friend is familiar with the case of Mary Kay Letourneau. She is the mother and teacher now in prison for "keeping company" with a minor. Your friend clearly knows she is playing with fire. (People mistakenly think this type of situation is nirvana for a teenage boy, but this is far off the mark.) Perhaps the thing for you to do is Google the name of the aberrant Ms. Letourneau, print out the material, then pass it on to your friend. Though you have no legal obligation to alert the appropriate agency in your town (because you are not a teacher or a doctor), you may decide that that is what you need to do. Ethically, this decision is not a straight shot because you will have to factor in how you would react to whatever consequences might come about. Let's hope the "reading material" does the job.

—Prudie, meditatively

Dear Prudence,

I've been in a relationship with a wonderful man for the last four years. Although the intensity and honeymoon phase have ended, we still love each other very much. Recently, I met someone else who has the same characteristics and personality of my significant other. This man has been showering me with attention, sending flowers and cards. He completely dotes on me ... opens doors for me, won't let me carry things, and the man literally threw his coat down over a puddle on the passenger side when he parked so I wouldn't get my shoes wet! He was in a bad 25-year marriage and has been divorced for four years. He tells me he wants to live his life with me, and we speak on the phone for hours at a time. My significant other travels a lot, so I've been able to spend time with this other man, and I'm falling hard for him. My significant other doesn't know anything about this, but the "other man" does know about my four-year relationship. He hasn't asked me to end it, but he's indicated that when "things fall apart" with my significant other, he will be there and wants to marry me. I think I'm in love with two men! Is that possible?