Dear Prudence

Moving Violation

I brought my ex-boyfriend to help my widowed friend clear out her house, and he helped himself to her stuff.

Mallory Ortberg
Mallory Ortberg

Sam Breach

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Dear Prudence,
“Trevor,” the husband of my friend “Emily,” recently passed in a very dramatic manner. He was a hoarder of expensive electronics. He hadn’t updated his will or life insurance policy to reflect his wife as beneficiary. Emily is entitled to the possessions within their house, with the rest going to Trevor’s estate. Trevor left the house in disarray, so we had to sort through the mess for valuables. Being short on time (and hands), I called an ex-boyfriend with whom I’ve remained friendly to help. Emily told the ex he could take one of the large (valuable) television sets if he helped. On both days my ex showed up late, wasn’t much help, and asked for nearly everything he saw, which was mortifying. The first day he left with four valuable Bluetooth headsets, a Bose Bluetooth speaker, and Xbox controllers. The second day he left with $250 cash and camping supplies.

Throughout the whole ordeal, he pestered us about which television he was getting. Fed up, Emily told him he wasn’t getting one because he had already been compensated fairly. Having loaded the final truck alone, I agreed with Emily. When my ex and I were alone in the cab of the truck, he yelled at me until I broke down in tears. I still have not heard the end of it.

I understand he’s an ex for a reason, and shame on me for bringing him around (I was completely caught off guard by his greed). But he still thinks we owe him the amount of money he could make from selling a television. How should you compensate “friends” for helping move? And while we are at it, how can I be better at picking men?

—Still Stunned

First and foremost, give yourself credit for no longer dating this guy. Second, delete his number and block his calls from your phone. If you feel like you must say something before doing so, try: “I asked you to help a grieving widow sort through her husband’s possessions. In exchange you’ve received valuable electronics, camping supplies, and cash. I am horrified and astonished that you are still asking for more. Please do not contact me again.” This is not a question of appropriate compensation for helping a friend move because a) he did not, in fact, help very much at all and b) he’s already taken at least four times the value of what you agreed upon. Do not blame yourself for his aggressive yet low-stakes jerkassery—the behavior you’ve described is jaw-dropping, and it sounds like you had no idea he would be so boorish, so unhelpful, and so belligerently selfish.

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Dear Prudence,
I’m a 28-year-old woman in a healthy, long-term relationship with a man I love dearly. We’ve been together for more than five years, and our relationship is still great. Our sex life isn’t as fulfilling as it used to be, but we have talked about it, and we are both OK with the way it is. Before this relationship, I was with an abusive older guy for six months. It wasn’t physically abusive, but he used our age difference to dominate me. I was an adult at the time but still quite young and naïve. Our sex life was quite passionate (and kinky), but retrospectively I find that period of my life icky, to say the least. He convinced me that the age gap was “romantic,” and I thought it was pretty hot. Several years later I still think about that man when I masturbate, and I feel guilty because I’m in a relationship, and I find my ex pretty gross. I know that my ex was manipulative, that he took advantage of our age difference, and that I’m never getting back together with him. Nevertheless he’s the main character in my fantasies when I touch myself. Is that unhealthy? Am I cheating on my boyfriend?


Having a fantasy is not cheating. You may find it helpful to think of your fantasies not as a maladaptive compulsion but as a sign that you now feel secure enough to process some of the traumatic aspects of your previous relationship. You sound very clear on the fact that you don’t want to get back together with this guy and don’t think the way he treated you was acceptable, so don’t be too hard on yourself for eroticizing your past from your present position of safety. That’s not to say it’s not worthwhile and meaningful to do a little more digging about what you’re getting out of these fantasies, the feelings they bring up, and what changes (if any) you’d like to make to your current sex life. Working out past trauma in a healthy, safe, solo environment is not unhealthy, but if you were to discuss this dynamic with a therapist, you might find a great deal of relief in articulating your desires, your disgust, your regrets, and your experience.

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Dear Prudence,
My husband and I made friends with another couple, “Katie” and “Steven,” last year. We have kids around the same age, and we get together a few times a month for backyard dinners and drinks. Recently, I remarked to Katie how much her children resemble her, and she replied that she hears that all the time. I jokingly asked how Steven feels about that, and she said: “Well, Steven’s trans. Didn’t you know?”

I didn’t know. It hadn’t occurred to me. I was so surprised that my reaction was something along the lines of, “Oh. Cool!” And then the conversation naturally shifted course. I’m concerned that maybe I underreacted. Gender identity is important, and I can’t begin to imagine what Steven went through before and during his transition. My husband and I consider ourselves to be LGBTQ allies, and I want Steven to feel comfortable and supported in our home. We’ve seen them a few times since and nothing seems weird or awkward, so maybe I’m just overthinking this. But could or should I have responded differently? It didn’t feel like a coming-out conversation, more like a casual disclosure of information. Still, I’m worried that I said the wrong thing, and I’d love your perspective.


You took your cue from Katie, who made it clear that this is information she (and presumably Steven) are comfortable with you knowing but that didn’t require a serious, involved follow-up conversation, and your response in that context was wholly appropriate. You’re likely right in assuming that Steven has gone through a great deal before and after transitioning, but that doesn’t mean he wants to go into detail about it with even the friendliest of neighbors. Steven and Katie already do feel comfortable and supported in your home, and there’s nothing you need to do here except continue to be friendly and welcoming and to take your neighbors’ cues on the subject of his transition.

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Dear Prudence: How do I get my hearing family to accept me?

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Dear Prudence,
My boyfriend and I (we’re both guys) have been together three years now, and one of the few recurring struggles I have with him is about his phone usage. He checks emails, texts, and social media notifications and plays games constantly, sometimes in the middle of our conversations. Once he did this while I told him a really emotional story about my family.

We’ve talked about this, and he admits that it’s inappropriate, but he still reaches for his phone all the time. It may stem from our different families: His is a small family full of introverts who don’t do much chatting at meals and who all spent time alone in their big house; mine was a large family in a small house where conversation was constant and you were expected to give the speaker your full attention. His work sometimes requires him to check the phone. I want to respect that and to be understanding of our personality differences, but I’m having a really hard time accepting that he “just can’t” change. Please help!

—Put the Phone Down

The fact that your boyfriend comes from a small, quiet family does not mean he is inexorably doomed to be a phone-obsessed bore any more than the fact that you come from a large, chatty family means you are fated to shout at the dinner table. He’s acting badly, and you want to see signs that he’s willing to amend his behavior. You’re not asking for total phone abstinence (and with his work that wouldn’t be possible), but at the very least, if you’re trying to have a heartfelt conversation with him about your emotional history and his eyes are glued to his phone, you can and should say, “Would you please put your phone away for a minute? I’d like to have your full attention.” If he’s genuinely interested in spending less time on his phone, there are tons of apps that offer a variation on “do not disturb” mode so that users can set aside blocks of time when their phones aren’t accessible; he has plenty of tools available to him if he wants to make a meaningful change in his habits. But the willingness is key—if what he wants mostly is for you to get off his back about it, all the Offtime in the world won’t make a substantive difference.

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Dear Prudence,
I’m filled with resentment toward my husband, and I don’t know how to move past it. He spent most of our 20 years of marriage as a high-functioning alcoholic. He’s been sober now for two years but still struggles with adult responsibilities like parenting, managing finances, and getting out of the house for a social life. Doing it all alone is burning me out. I would like a partner in raising our kids and running the house, but after so many screw-ups I can’t trust him to show up and follow through. He’s sober, but the disappointments keep happening. I’m lonely. And I feel slighted by the way our marriage is turning out. My negative outlook is taking a toll on the entire household. How can I let go of the past, make do with what I have, and be more positive?

—Lonely Marriage

I don’t think it should be your first and best option, but have you considered leaving him? It should at least cross your mind as a possibility, I think, if only as a reminder that you are not permanently bound to his side from here to eternity. Sometimes it helps to consider every possibility, if only as a reminder of one’s own freedom to act—you could leave him. You may decide not to, but the fact that he has gotten sober does not necessarily mean that your marriage has survived the past 20 years of active alcoholism. If you don’t trust him, if his irresponsible and unreliable behavior has continued even after he has quit drinking, then I’m not sure how you can “let go of the past” when the past is still happening. So whether you stay with your husband or not, I don’t think your goal should be “let go of the past” and “make do,” because that just signs you up for another 20 years of picking up his domestic slack.

Whether you find Al-Anon meetings or individual counseling helpful, spend some time out of the house articulating your own frustrations, desires, and hopes so that you can get a better sense of what you want out of your marriage and how you can ask for it. Identify particular tasks or responsibilities that you no longer have the bandwidth to be responsible for and resign from those positions. Implicit in your letter is a sense that because your husband is finally sober, you no longer have the right to experience resentment or ask something different of him. I don’t think that’s true!

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Dear Prudence,
I recently heard from my parents that my college-age cousin has come out as trans. They heard from other family members and were told it was a secret. I’m not friends with my cousin on Facebook, but on her public profile she’s using female pronouns and a typically female variation of her name. All of this tells me that if it’s a “secret” that’s less in the sense she’s not out yet than in the sense that the family doesn’t quite know what to do with this information. My family has always been very supportive and open-minded. I’m a lesbian, and I’ve only ever seen love from my family.

I think it’s fantastic news, and I’m very happy for her. I’ll be seeing her at Thanksgiving for the first time in a year, but I’d love to reach out now and send her an email telling her that I think this is great news, I support her, I am there for her, and I can’t wait to see her at Thanksgiving. Is this appropriate, or should I wait until I see her at Thanksgiving and she comes out to everyone?  We don’t usually talk aside from when we see each other family functions.

—Caring Cousin

I think you should follow your cousin’s lead and let her come out to you. That doesn’t mean you can’t send a friendly email to say hello and to say that you’re looking forward to seeing her at Thanksgiving, as well as telling her a little bit about how your year has been. But give her the opportunity to come out to you when she feels ready, rather than because you’ve heard the news through the family grapevine.

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