Dear Prudence

Help! My Fiancé’s Ex Is Our Neediest Wedding Guest.

Read what Prudie had to say in Part 1 of this week’s live chat.

A woman looking annoyed, and another woman looking confused at a map
Photo illustration by Slate. Photos by MykolaSenyuk/iStock/Getty Images Plus and Koldunov/iStock/Getty Images Plus.

Daniel Mallory Ortberg is online weekly to chat live with readers. Here’s an edited transcript of this week’s chat. 

Daniel Mallory Ortberg: Good morning, everyone! Let’s chat.

Q. My fiancé’s ex is our neediest wedding guest: I’m getting married in a few weeks, and I have prided myself on being a roll-with-the-punches bride who knows the most important thing is that I’m marrying the best guy in the world. The problem is his ex (they dated for three years when he was in college over a decade ago), who still obsessively refers to him as her bestie (a level of friendship I’m not sure he feels, though I know he cares about her, and his sense of loyalty is my favorite thing about him). She decided at the last minute that she was traveling in to attend and now needs her hand held every step of the way. I found her train tickets and have been helping her figure out public transit and even activities for the several days she’ll be spending in town afterward.

Now she’s booked herself a hotel that’s farther out than where any of our other friends or family are staying (on a bus line, since she claims she can’t afford an Uber) but is hinting around that she’d like us to find her a ride all weekend or ferry her around. My fiancé is bighearted enough that I’m convinced this will end with us picking her up and/or driving her home on our wedding day. How do I ask him to let her just figure it out on her own without sounding like a jealous shrew?

A: “I’m having a hard time dealing with all of Krista’s requests, and I’m worried that because you’re so friendly and accommodating this will ultimately end in her asking you for a ride on our wedding day. I want to draw the line there. I like her as a person and I understand that your friendship is important, but whatever anxiety she’s having around our wedding is starting to manifest in really overwhelming, obsessive preplanning. I haven’t had to help anyone else find train tickets, plan a public transportation route, or decide what tourist activities they want to do afterward. I don’t think that’s a normal part of wedding planning, and it’s just too much. I think it’s reasonable at this point, if she asks for more favors from either one of us when it comes to travel or logistics, to encourage her kindly to solve the problem on her own and tell her we won’t be able to offer her rides or troubleshoot any more of her concerns. Does that strike you as reasonable? It’s important to me that we both have one another’s full attention on our wedding day and our honeymoon, and while I’m thrilled to celebrate with all of our friends and family, celebrating is all I want to do with them—not play host.”

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Q. Celebrating Diwali—without anyone who actually celebrates it: In the spirit of cultural awareness, my work colleagues want to celebrate Diwali. I gently suggested that it would be wrong to introduce the topic without having invited any people who actually celebrate this festival. They responded that they could show a video. This still strikes me as very wrong. Can you please give me the language to explain why it’s wrong? We are a small startup with six white women.

A: I certainly have some questions! Are your colleagues hoping to host this celebration during office hours? Is this an off-the-clock social thing? What’s the general principle behind this thought, and is it in any way work-related? If all that comes of it is that your colleagues decide to show a video about Diwali and gesture toward the celebration with food or drink, I don’t think you have much to worry about or much of an intervention to offer. (It doesn’t sound like anyone’s proposing a full five-day celebration.) Mild curiosity isn’t in itself offensive, even if this does strike me as mostly irrelevant where work is concerned. But if they’re proposing acquiring “costumes” or coming up with an on-the-clock patchwork version of Diwali as a form of entertainment, I think an objection on the following grounds is reasonable: Celebrating a religious, culturally significant festival in the workplace when none of you practices that religion or is a part of that culture goes well beyond respectful curiosity, creates the possibility for controversy where none need exist, and doesn’t really cultivate an efficient workplace.

Q. My sister’s boyfriend is a loser: My sister was the primary caretaker for my parents before they died, and she inherited their house and cars. While my parents were alive, my boyfriend and I were at their house every weekend to help my sister out with repairs and take care of my parents. Now that my parents are gone, she’s allowed her boyfriend to drive my dad’s car and smoke in it. Now he’s showing up to the house to repair it and move in. He’s never met my parents and she’s already allowing him to take over everything my parents worked so hard for. I’m angry because I feel like it’s disrespectful to my parents. At the same time, I want her to be happy, and I understand that she’s an adult. How can I get over this? Please help.

A: On the one hand, grief can manifest in many strange and complicated ways in one’s life, and it makes a lot of sense that you’d feel sensitive and protective about your parents’ things. To that end, if there are any small mementos that you’d like to keep in your own home, now might be an opportune time to ask your sister if it would be all right for you to come over so the two of you can pick a few items together for you to take home.

But I also think that you’ll need to let go of some of this defensiveness—your sister isn’t inviting her boyfriend to move in with her because she wants him to take over your parents’ memory. She’s inviting him to move in with her because that’s where she lives, and she wants to live with her partner (a perfectly mundane and reasonable thing to do). She’s been a full-time caretaker for two people, and if she wants help keeping the house repaired and a little companionship after what must have been a very challenging time, I think that’s pretty understandable and not at all disrespectful to your parents.

I agree that smoking is an unhealthy habit, and it’s unlikely to improve the car’s resale value, but one of the painful things about this situation is that cars don’t last forever or tend to retain a lot of their initial value. These cars will never become permanent testimonies to your parents’ memories. Your feelings of resentment and suspicion are understandable, given that you’re grieving, but I don’t think it’s appropriate to share them with your sister. I’d encourage you to see a grief counselor, start a journal, or vent to a friend who doesn’t know her. Think of it this way: No one who moves into that house next is likely to be someone who knows your parents; it cannot be the only or even the primary way your parents can be remembered. That (at the risk of sounding trite) is what memories are for. I’m so sorry you lost your parents and I hope you can find a number of productive and constructive ways to talk about your grief, and try to get some distance from your sister’s domestic arrangements.

Q. Should I tell my boss how to be a better parent to his daughter? I work for an indie video game studio that makes games aimed at young adults. Our company values itself on being progressive, especially when it comes to content having to do with gender and inclusivity. I generally love my job—there’s a lot of writing involved, and everyone seems on board with the message of tolerance and empowerment that I’m trying to communicate through our stories.

But at lunch recently, my boss was telling me about his young daughter’s troubles with making friends at school. She is interested in sci-fi and video games, and she’s frustrated that the girls in her year are only interested in “girl things.” My boss didn’t follow up with “And so I reminded her that video games are ‘girl things’ too” or “Let’s try to not think of activities in terms of gender.” He sort of dropped the story there with a shrug of the shoulders. In other words, he seemed to imply that he was on the same page as his 10-year-old daughter, as if to say, “Yeah, it does suck that you like video games and girls your age are only interested in girl things!”

It’s been a couple days now, and I’m kicking myself for not gently asking him if he agreed with what she said or if he planned to talk to her about mindsets toward gendered hobbies at any point. I also know that it’s really not my place to do that! I’m an employee of his, and it would likely be crossing a line to grill him on his parenting. With that said, we’re a very small team, and we’re generally pretty friendly and casual with each other; we know quite a bit about each other’s home lives, and he’s asked some fairly personal questions of me before. Where’s the line here? I hate to think that the figure at the helm of our nice, liberal studio is harboring some crappy ideas about the very people we’re crafting stories for.

A: I think if your boss has asked you some ”fairly personal questions” before, the most important thing to do going forward is to clarify when you’re not comfortable answering personal questions so that he stops asking you, not to try to go over his parenting strategies with him again. That said, I understand why that moment stood out to you, especially given that it was directly related to the kind of work that you do. I think there would have been room in the moment to mildly push back, like, “Oh, I liked video games as a kid, and I hope she can find other girls who want to play too,” or mentioning that your target audience at least includes girls who like video games. But if that was a one-off remark and he’s otherwise a fairly thoughtful boss, I don’t think you have to worry he secretly thinks all girls except for his daughter only care about “girl things.”

Q. My in-laws’ miniature poodle is a menace: I’m writing this letter at 5 a.m. and have been up since 3 a.m., so that should give you an idea of how this is going. We visit my in-laws once a month or so, typically spending the night because they live 2½ hours away. My in-laws have a 6-year-old miniature poodle who spends a good 12 hours a day home alone, due to their demanding careers. And yet, they insist on taking the dog out at least twice in the night because “she can’t be expected to wait all night.” The result is two to four slamming doors (they are not quiet people), and then my mother-in-law barging into the guest room because “the dog missed us” and will not let us refuse to take her. The dog is not particularly well trained, and she cries whenever she is awake and not being petted or held. This means when I’m not awake because of the door slamming, I’m awake because the dog is crying in the next room over. She also refuses to sleep on the floor, so when she does make it into our room, there is an animal sandwiched between my partner and I, one that barks and growls whenever you move.

Tonight, my mother-in-law let the dog into our room, and when my partner protested, she yelled (at 3 a.m.!) that they have plans in the morning and can’t be up all night with the dog. My partner ended up taking the dog and going to sleep on the couch (because the dog refuses to be left alone at night). This can’t continue! This is a dog, not an infant. I am a huge dog lover (our own 12-year-old dog sleeps through the night on his own bed in the living room) and have sympathy that she spends the majority of her day alone, but as a result of these visits I lose a weekend of sleep at least once a month. My partner has broached the subject several times with some perceived success, but as soon as it’s bedtime it’s like the conversation never happened. (It is not out of character for this to happen with my mother-in-law, and my father-in-law typically just goes with whatever she wants and says.)

In frustration tonight, I said I am done sleeping over at my in-laws’ house, and right now I really mean it. I feel like a horrible person because I catch myself looking forward to when, several years from now, I’ll finally be able to visit without their dog around. I can’t enjoy the weekend with my husband’s family when I’m borderline delirious from lack of sleep. I find myself in tears from frustration. We did briefly try inviting my in-laws to our house for weekends instead, sans dog, but they showed up with her anyway. They were upset, rightfully so I suppose, that we bring our dog along when we visit. What can I do, short of refusing to spend the night anymore?

A: I hope I don’t sound too pessimistic when I say I think the odds are excellent that long before this poodle dies, your in-laws will probably replace her with another equally badly trained and sporadically neglected one, so I wouldn’t count too much on getting free of this situation in a few years. But your solution is an elegant and an obvious one, and it should never have gotten to the point of weeping in the small hours of the morning for you to have to float it as a possibility—of course you and your husband should just visit during the day from now on. You don’t have to have an argument about this, or get into a back-and-forth about whether you like the dog. Just plan your visits a little earlier in the day so you have time to drive home before it gets too late. Say it cheerfully, say it matter-of-factly, but get on the road before night falls and then sleep soundly.

Q. Re: My fiancé’s ex is our neediest wedding guest: I think it also may be helpful to assign a random friend to play interference with her. I definitely think you need to tell your future spouse that you need clear boundaries with her, but also ask a friend to jump on that grenade. I did this when I was a bridesmaid for my friend who had a particularly needy guest.

A: That might be a good option too. I’d also just want to talk this through with your fiancé more than once to make sure you were both on the same page. Has her behavior struck him as unusual throughout this process? Is she like this outside of wedding planning? Does he say “Yes” to her a lot because he’s this way with all of his friends or because he doesn’t feel comfortable saying “No” to her? Day-of buffers are great, but so is a cheerful “Oh, I don’t know how to answer that question about bus routes for you—I’m afraid we’ve got a lot on our hands already in planning for the wedding, but I’m sure you can find someone to help you out.”

Q. Re: Celebrating Diwali—without anyone who actually celebrates it: Please discourage this. It’s idiotic. No one in your office celebrates or seems to even have a clue what Diwali is about. I’m Hindu, and it’s frankly insulting to see people who don’t celebrate Diwali “dress up” like it’s Indian Halloween or something. Ask your co-workers if they are planning similar celebrations for other religions no one celebrates in the office.

A: It just seems like the absolute best-case scenario is that it wastes time during which you could be working. And there are other, better ways to waste time at work! Framing this as potentially off-putting to any future Hindu clients or hires might be a good way to discourage your co-workers too: “What kind of message would this send, and is that the first impression we’d want someone to have of our company?”

Q. Repaying loans from a friend: Over the past several years, a very close friend has been helping me pay my mortgage. I finally realized that I just couldn’t afford the house, and I sold it. I made some money, which needs to last as I am older and no longer working full time, and I need to find another place to live. Certainly I need to repay some of the money, but over time it amounted to a lot, and the friend and I have discussed my inability to repay it all. But I want to give her some of my proceeds. How do I decide how much to pay now?

A: I think you should ask! This close friend of yours sounds remarkably generous and pretty easygoing about when or whether you pay this money back, so I don’t think you have to worry too much about how to broach the subject. Given how long you need to make this money last, and how much of it you want to earmark for finding a more affordable place to live right away, is there a ballpark figure you could offer her that wouldn’t put you in dire financial straits? Would they consider accepting a smaller recurring payment for a certain number of months or years, or would they prefer a lump sum? Which of those options would be easier for you? I’m sure they’d appreciate it if you do a bit of the calculations in advance so they know you’ve been thinking actively about how best to repay them. “I’ve been thinking of X percent of the proceeds from selling the house would still enable me to pay $Y for a smaller apartment and save Z for retirement. Does that sound good to you? What do you think is reasonable here?” (Maybe invite them out for a nice dinner on you, within your budget, in the meantime.)

Q. Re: Celebrating Diwali—without anyone who actually celebrates it: I’m the original poster of this question. It’s during work hours but is totally unrelated to our work. This is in response to wanting to cultivate more diversity in our workplace (a good thing), so once a month we will have a cultural celebration led by one of the team members. This is the first event, so I’m not sure what’s going to happen. I suspect it’ll be food and an explanation of the holiday—not sure if we will be doing more than that.

A: Oh, man, I think it’s definitely important to push back here. If the stated intention is to “cultivate more diversity,” the way to do so is not for six white people to celebrate a festival they have no connection to. Moreover, it might actively make it harder to attract candidates of color if they get the (correct) impression that your workplace is clumsy and uncomfortable around issues of race and cultural heritage.

Q. Re: Celebrating Diwali—without anyone who actually celebrates it: I think the letter writer’s follow-up comment is actually OK, if she turns it away from a celebration and turns it into more of an education. Learning about a new religion or tradition is not bad; celebrating it is. If it is geared toward learning so as to make everyone involved more educated and aware and inclusive, that’s fine. Otherwise, I agree with: no celebration.

A: I do agree that if she has the assurance that it’s just a brief lesson and a lunch, then that’s probably fine. But I do worry a bit about whether her co-workers are actually going to stick to that—she says she thinks they won’t be doing anything else, but it may be that some of the other women in the office want to take it further. I’d seek clarity first: If it really is just a few bullet points about the festival’s history over lunch, then I’m on your side and would participate; if they’re planning on encouraging costumes or something more participatory, I’d push back.

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Classic Prudie

Q. My broken-hearted ex wants to pay me to hang out with him: I’m a college student who, a little over a month ago, broke it off with a guy I’d been in a relationship with for 10 months. There was no spark, and I felt like being single and exploring other options. My ex is completely, unabashedly in love with me still and has been taking it really hard. He calls and texts me constantly asking for me back.

I’ve been broke lately, and I mentioned to him off-hand that I’m worried about funding my study abroad this summer. He then offered to pay me to go on dates with him—just a couple dates, until I leave next month. No sex, just “hanging out, the way we used to”—dinner, movies, etc. I’m not worried about the ethics of being paid for something like this (before his offer, I was considering using a get-paid-for-dates service, but I’d rather do that with someone I know); the problem is that I can’t shake the feeling that this is wrong for me to do with him and would only exacerbate things. I feel sorry for him. It seems pragmatic and makes sense in theory—he misses me, so he gets to date me, and I get money for my travels—and he’s a grown man who can make his own decisions about what’s best for him, but I feel like it’d be crazy for me to take him up on his offer. Thoughts?

And find even more letters in the Dear Prudie archive.