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Dear Prudie,

Several years ago I dated a woman named “Rhonda” for three months. I broke up with her after her sister “Amy” revealed to me that Rhonda was born “Ron” and showed me ample evidence. When I confronted Rhonda about her being a transsexual woman, she broke down and confessed that she was going to tell me, but only after we had been intimate! (Luckily we hadn’t been yet.) It wasn’t her transsexuality that ended the relationship, but her deception; I am not a transphobic person. Rhonda took the breakup badly and stopped speaking to Amy, and on top of that their parents took Rhonda’s side and accused Amy of trying to ruin Rhonda’s life out of jealousy. Later, Amy and I began dating and eventually married. Her parents refused to attend the wedding as a show of solidarity with Rhonda, despite Amy’s attempts to reconcile with all of them. Now we are expecting our first child and Amy’s parents have expressed tentative interest in being a part of their grandchild’s life. I, however, want these people to have nothing to do with my child or my wife. They are a toxic influence and their enabling of Rhonda’s deceptive behavior is appalling to me. My wife disagrees. How can I help her cut ties with these horrid people?

—Trying to Protect My Family

Dear Trying,

So much for sisterly solidarity. Yes this is a tale of bad judgment, but if Rhonda erred by omission, Amy’s sin was one of commission. She collected a dossier on Rhonda and presented it to you, meddling in her adult sister’s private life. You are stuck on the fact that you feel misled by Rhonda, so let’s examine that. There are no hard and fast rules about what one is obligated to tell a potential sexual partner, beyond the necessity of alerting them to one’s communicable disease status. You were slowly getting to know Rhonda, and I think two people looking for a serious, intimate relationship are obligated to divulge facts about themselves in a timely way that a reasonable person would feel deceived not knowing. For example, revealing that one had been married previously, or has children, or can’t have biological children, or has a significant medical condition. I think being transgender falls in this obligation-to-disclose category. I know that what to tell and when is an issue of debate in the LGBT community, so for perspective I spoke to Jennifer Finney Boylan, author of Stuck in the Middle with You, a memoir of her transition from being a father to a mother. She agrees that where intimate relationships are concerned honesty in general is best, but when to reveal that one is transgender is a choice made by that individual. A generation ago, she says, transgender people were told by their doctors to erase their pasts and live a stealth life, which caused a lot of anguish and meant people traded one secret for another. Today, she says, some trans people who have had reassignment surgery assert they simply had a birth defect that was corrected, and therefore their past is nobody’s business. Boylan does point out, however, that in the age of the Internet trying to keep the fact of a gender change hidden can become a terrible, and hopeless, burden.

But above all, Boylan noted the violation committed when Amy decided to out Rhonda, a revelation that was not hers to make. I hope you can understand how Amy’s act cleaved her family and shattered her relationship with her sister. Now that you and Amy are about to have your in-laws’ first grandchild, you’re asking for my help to undermine any chance this family might find some way forward. It’s you, however, who has to examine whether the presence of Rhonda makes you so uncomfortable that you would prefer to demonize your in-laws and sever them from your child’s life. It is you who has become the toxic influence. And as Boylan points out, now that you and Amy are about to become parents, think about how you would react if your own child turned out to be transgender, which might help you better understand all your in-laws.

—Prudie

Dear Prudence,

One of my best friends went through a rough patch a few months ago and used substances (both legal and illegal) to cope, eventually resulting in a DUI. I live in a “party” city where I moved last year for a job. She and a mutual friend expressed interest in coming to visit, and she told me she was getting out of probation early. She’s been having money trouble so I bought her plane ticket. They came, they partied, and they spent most nights blackout drunk despite my talking to them about their behavior. It would be an embarrassing and regret filled weekend, if they could remember. I found out after she left that she had not gotten off probation early (in fact her probation was twice as long as she had revealed), or told her officer she would be leaving the state. She also was not supposed to be drinking while on probation. I now feel like an accomplice to her crimes, especially because I purchased the ticket, but also because I now know she really needs more help and supervision. Neither her parents nor our friends see this as an issue. Should I contact her probation officer anonymously and tell her what happened (I have Facebook photos to prove it), try to get her help in some way, or sweep it under the rug like everyone else?

—Don’t Have Another

Dear Don’t,

The drunk driver who killed two people and plowed into two dozen others at the South by Southwest festival had a previous DUI conviction. I wonder if his friends are now wishing they had done more to stop him. Your friend lied to you and made you party to a parole violation. She also made you party to her nonstop partying. It must have been lovely to catch up with her while holding her hair away from the vomit. She has amply demonstrated that she’s a danger to herself and others, and it’s the others I’m most concerned about. It’s very sad for a young person to let her life be ruined by alcohol, but it’s even worse if she’s going to also endanger innocent people. It’s astounding that her parents aren’t alarmed by her current condition and what lies down the road if she doesn’t stop. But maybe having oblivious parents is a source of some of her troubles. One thing I learn over and over again in this column is how difficult—and sometimes impossible—it is to save someone else. But you have an unusual opportunity to force your friend to address her problems. So I encourage you to contact your friend’s parole officer and tell her what went on. It’s true this could possibly land your friend back in jail, but at least there she’ll be sober. The result could also be that she is required to go to rehab or get more serious monitoring. Let’s hope that this time when the criminal justice system acts, your friend finally comes to see that gravity of the choices facing her.

—Prudie

Dear Prudence,

For decades I’ve used my initials in lieu of the first name(s) I was christened with. My family and old friends use my given name, but professionally I’m known by my initials. Many people—among them prospective employers, salespeople, new acquaintances—give me a hard time about my choice. They first ask, then frequently demand to know my “real” name. I’ve smiled and murmured something about preferring my initials, but they persist and then the conversation gets hijacked by the subject. This happens so frequently and some people get so vehement about it that I wonder if I shouldn’t just acquiesce and give them my full name? Or am I making too much of this?

—D.A.

Dear Douglas Andrew? Donald Alexander?,

It’s fair to ask those who use initials what they stand for—once. But after you’ve said, “It stands for Don’t Ask,” and explained you simply prefer to go by D.A., the questions should stop. Maybe the reason E.B. White retreated to his farm in Maine was so that people in New York would stop trying to find out that his first name was “Elwyn.” But since you spend so much time refusing to reveal your name, you have to consider whether life would be easier if you did. Simply saying, “It’s Derek Anthony, but I go by D.A.” might defuse the whole thing, and would be a good strategy to use with prospective employers. But of course it’s your right to stand firm and firmly change the subject. As for those persistent salespeople, you can tell them you’d like the full name of the manager.

—Prudie

Dear Prudence,

In the heat of an argument with my wife I often detach myself from my emotions and try to look at what is happening objectively. This inevitably irritates her because she thinks I am both acting morally superior and not really being objective because too often I side with myself. But if I can objectively pick apart and present both sides of my wife’s and my arguments, and it turns out I’m right, shouldn’t this help? If not, what is a better way of ending our arguments and stopping future ones?

—Neurotic

Dear Neurotic,

It is gratifying to always be right, but for the sake of argument, I’m going to give you some phrases to use to try to end some of your marital spats in a more productive way. Try sprinkling them liberally, and see if your life doesn’t improve: “I hadn’t thought of that.” “You make a good point.” “That’s a fair criticism.” “I see what you mean.” “Yeah, that’s true.” “You know what? You’re right.”

—Prudie

Discuss this column with Emily Yoffe on her Facebook page.

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