Dear Prudence

I’ve Been Sleeping With My Friend for Eight Years. Should I Tell His New Wife?

I don’t want to lose our friend group over this.

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Dear Prudence,

Most of my friends have known one another for 15 years (we’re mostly in our 30s). I’ve been sleeping with one of them, “Jake,” once or twice a month for the past eight years. He’s been with his girlfriend for six years (I know). I liked our arrangement because it truly was no strings attached. Jake’s girlfriend has never really been part of our friend group, so I don’t know her very well. Apparently she felt uncomfortable because everyone in the group has an advanced degree, and she didn’t go to college (which is weird because we hardly ever bring up education or career stuff when we hang out).

Two years ago, Jake proposed to her. I thought he’d stop hooking up with me then, but he still wanted to. After a few more months, the guilt felt overwhelming, and I said I just wanted to go back to being friends, and we stopped sleeping together. But I kept wondering if I should tell his girlfriend he’s been cheating on her for the entirety of their relationship (I know he’s still sleeping with other women). I decided against it because I’m generally very private, and if I confessed, everyone in our friend group and in our small town would know. I also didn’t want to lose my friends over this (although maybe that would’ve been a good punishment for my behavior). I thought an anonymous note would’ve been creepy. They got married officially a few weeks ago, and it’s still irking me that I never told her. She’s “soooo happy.” I guess now if or when she finds out and they get divorced, she’ll get half of his money (he’s quite wealthy, and she doesn’t make much). What would you do in this situation?

—Sour Grapes vs. Honeymoon

A slightly loaded question! Let’s leave aside how to respond and take a look at what you’re working with emotionally: Part of you wants to be punished and thinks you deserve to lose your friends. Part of you is desperate to keep your friends. You’re protective of your privacy, presumably at least in part because you fear judgment from others, but this strictly guarded privacy has also left you fairly lonely and without solace, since you can’t discuss this with friends. It also doesn’t take much reading between the lines to see how much you resent this woman, from your dismissive depiction of her wedding day as something that makes her “soooo happy,” to your obvious contempt for the fact that she’s felt nervous around her now-husband’s friends for years.

The sex you’ve had with Jake over the past eight years has never been “no strings attached.” You’re as surrounded by strings as if you had run headfirst into a giant ball of yarn. It’s just that most people can’t see the strings—except for you. For a while, that worked out fine, and you could pretend to yourself that you didn’t have any expectations, but now that fiction has collapsed entirely, and you’re desperate for a way to untangle yourself, even as you fear alerting anyone else to the stringiness of your situation. I can’t advise you to speak to Jake’s wife about your relationship with him, since your motives seem straightforwardly punitive. You don’t want good things for her, you don’t care about her, and you would only say something now to hurt her. The kindest thing you can do is leave her, and Jake, alone. Instead, spend some of this time and energy with a therapist figuring out what you want from your personal life in the next eight years—something that looks utterly different from the last eight.

Help! My Ex-Husband Spoils Our Daughters With Lavish Gifts.

Danny M. Lavery is joined by Isaac Fellman on this week’s episode of the Dear Prudence podcast.

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Dear Prudence,

I still live in my hometown, as do my parents. My sister lives far enough away that a day trip is just about manageable, but since the pandemic, she’s cut down a lot on her visits. She has a new boyfriend whose family lives in their town, and my sister wants us all to come to her for Christmas. My parents really want me to go—my mother recently lost a sister and really wants to be away from home and surrounded by family. But I really don’t like my sister. She’s spoiled and treats me poorly. I don’t think she likes being around me, either. She almost never texts me, but she keeps texting me about Christmas and trying to get me to go. I really don’t know why. We don’t enjoy each other when we’re together. I don’t like the way my parents spoil her and she gets everything she wants. Most of all, I don’t want to travel to an unfamiliar city and hang out with people I don’t think are being very careful about the pandemic. I’m being extremely cautious. I feel bad for my mother. I know she’s still grieving and being with her family is important, I just don’t want to be around my sister. Should I stay home? Is there a way I can tell my parents how I feel about her without stressing them out? Family is so important to them, I just don’t know what to do.

—Traveling Tenterhooks

I don’t think there’s a way to tell your parents that you don’t like your sister without stressing them out at least a little, no matter how gently you couch it. You may want to have an honest conversation with them someday about their apparent favoritism, although I’d recommend waiting until after the holidays and the early months of your mother’s bereavement before broaching the subject, especially if you’ve never discussed it before. It will also help to have a sense of your objectives before starting such a conversation. Do you want them to affirm that they treat the two of you differently? Do you want them to commit to change, or do you just want them to hear you out? How will you handle it if they disagree or start trying to justify themselves?

The good news is that you don’t have to have such a big-picture conversation in order to make a decision about this particular trip for this particular holiday. I imagine any Christmas gathering your sister is planning will involve being indoors and unmasked with multiple people you don’t know well, some of whom aren’t following basic coronavirus mitigation guidelines. You don’t have to say, “I don’t like you that much” in order to decline her invitation. You can just stick to the facts. Your parents might be disappointed, but it sounds like you already see them fairly regularly, and you can always “stop by” via Zoom for half an hour on the day. Yes, the holidays can be a big deal, but it’s also one day out of the year and one Christmas out of many. “Family is important” can be a lovely sentiment, but it doesn’t mean you’re obliged to say yes to everything your family wants you to.

Dear Prudence,

My son started virtual kindergarten at the local public school this year. When we registered, I was pleased to see that there was a nonbinary option under “gender.” However, his teacher and other teachers at his school constantly address the students as “boys and girls.” I worry about the kids in the school who may be unsure of their identity and how this limitation may make them feel. I also worry about how this impacts what we teach our son and how it may subconsciously limit his worldview. I would like to raise the issue with the school, but I also want to be sensitive to my son’s teacher and not make her feel like I’m going over her head. Do you think I should approach the teacher directly? Or would the guidance counselor, or the principal, be more appropriate?

—Other Salutations

This will not be the first time your son encounters something in the world that’s different or even contrary to what you teach him at home. That’s the point of the world, and the point of home training—how to process new information, how to make careful judgments, how to ask questions, how to cultivate sound discernment, how to react to something that challenges what you know or believe without defensiveness or undue deference. It might be helpful to see this not as a problem but as an opportunity. Many things he encounters at school, from other kids, from you and his other relatives, on TV and elsewhere will play some part in shaping his worldview. Worldviews are meant to be shaped! And worldview shaping doesn’t happen once and for all at 5, never to be reassessed or reevaluated again. Hearing teachers say “OK, boys and girls … ” is hardly the only way little kids learn about gender. That’s not to say this doesn’t matter, merely that you shouldn’t worry that this is going to be the turning point upon which all your son’s classmates’ self-esteem and identity ultimately depend. You can gently speak to your son’s teacher about using gender-neutral forms of address, but keep it in perspective, then move on.

Catch up on this week’s Prudie.

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