Dear Prudence

Help! My Son Caught His Fiancé in Bed With His Brother.

I wish he hadn’t responded the way he did.

Man and woman kissing with a wedding ring next to them.
Photo illustration by Slate. Images by  natrot/iStock/Getty Images Plus and Siri Stafford/iStock/Getty Images Plus.

Dear Prudence is Slate’s advice column. Submit questions here. (It’s anonymous!)

Dear Prudence, 

Two months ago, my older son “Carl” was supposed to get married to his fiancé “Lisa.” Unfortunately, the night before, Carl discovered Lisa having sex in her hotel room with his older brother “Brad.” This was not out of character for Brad, who I have been estranged from for several years but who Carl remained in touch with. Of course, I was supportive of Carl immediately ending things with Lisa, and I managed the logistics of the canceled wedding.

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However, Carl decided to go a step further and set Brad’s car on fire. (It was not occupied at the time.) While I understand the impulse, I really wish he hadn’t done it, and I’ve told him as much. There’s now a whole legal issue going on between them and Carl is broke because of it (and because Lisa moved out so he’s paying all of the mortgage). I’m certainly going to continue being someone Carl can talk to, but how involved should I be in supporting him financially throughout this?

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—Not My Best Parenting Moment

Dear Parenting Moment,

You know, a while ago I did a Q&A with our editor in chief Hillary, and she asked me how my perspective on advice has changed since becoming a parent. This is a perfect example. Seven months ago I would have said, “Carl is out of control. It was fine for him to be upset but setting Brad’s car on fire was completely unacceptable. You owe him nothing.” And you know what? I still think that. I know that’s true. Let me be clear: Carl was dead wrong.

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But I now have a better sense of how much you probably want to make this better for your son. If I were to find myself in your situation 20 or 30 years from now, I could see myself dutifully writing checks to my son’s lawyers with the same energy I currently bring to picking up and sterilizing the little green giraffe he likes to chew on but also likes to throw from his stroller repeatedly. I could just take away the giraffe during walks. You could absolutely cut Carl off. But love for a kid makes you want to do things that don’t make sense.

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There is no “should” here. If you don’t feel moved to support him financially, by all means, don’t! But your letter suggests that you’re torn. So, I would say, support him financially in an amount that will not cause you to be resentful. An amount that you are OK parting with, knowing that it’s going to someone who did the wrong thing because you want to ease his suffering at this time. How much depends on your bank account. Maybe it’s nothing. Maybe it’s half the mortgage for six months. Maybe it’s his therapy copays. Actually, therapy should be required before you hand over a single dollar because he has problems that cannot be solved by money—or support from a loving parent—alone.

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How to Get Advice From Prudie

Submit your questions anonymously here. (Questions may be edited for publication.) Join the live chat every Monday at noon (and submit your comments) here.

Dear Prudence, 

I usually get along terrific with my mother-in-law, however, lately, she has been very overbearing. Anyway, we (MIL and I—husband was somewhere else) were in our vehicle driving to a special place for my kids, and our nephew (her grandson) was in the vehicle as well, she turned to me and said, “I hope (husband) is careful, you can’t afford to lose your meal ticket.” I turned to her and said, “Really??” She denied trying to be malicious, but I believe she was being mean.

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She called me yesterday and told me that I need to call her friend and get her daughter’s number because the company she worked for is hiring. I tried to explain that I can’t do that, (I am handicapped and unable to work), but she just kept going on and on. I finally had enough and told her to just stop. I may have been a little forceful, but she doesn’t listen otherwise. She got mad and hung up on me. She became a widow a few years back and one of her kids does not speak to her at all, her other child rarely speaks to her, my husband is the only one who is there for her consistently. We try to call her daily to be sure she is OK, and we include her on most of our outings. We go to her house and do chores and things for her that she can’t do. I want to know how to handle this. I told my husband that he needs to talk to her about this, but he doesn’t want to hurt her feelings.

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—Meal Ticket Mama

Dear Meal Ticket,

Your husband doesn’t want to hurt his mother’s feelings but he’s OK with your feelings being hurt. That’s not OK, and maybe if you frame it to him in that way he’ll see why. If he doesn’t, take both of the sentences you wrote that start with “we” and change that to “he.” He can be the one to check on her, go on outings with her, and do chores for her. Not you. She’s not your mother and she doesn’t respect you or treat you well—so why would you be involved? No, that won’t be great for your marriage but neither is the way you’re living now.

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Dear Prudence, 

I have been seeing a woman for almost five years. She will not have sex with me and will not take her single status off of all her social media apps. She says she has no sexual urge and wants no labels, she swears she is not going to be with anyone else but you know that is crazy right? What should I do?

—Think I Am Being Scammed

Dear Scammed,

Stop giving this woman money and see what happens. I have a feeling the relationship will end without your having to do anything. Yes, I know you didn’t say it but I have seen enough Catfish and Love After Lockup to have an idea of what’s going on here.

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Give Prudie a Hand in “We’re Prudence”

Sometimes even Prudence needs a little help. Every Thursday in this column, we’ll post a question that has her stumped. This week’s tricky situation is below. Join the conversation about it on Twitter with Jenée @jdesmondharris on Thursday, and then look back for the final answer here on Friday.

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Dear Prudence,

I own a condo. During COVID, my girlfriend “Anna” moved in. It wasn’t a good fit. Our personalities clashed too much and we both pretty much agreed to break up. I thought we could still be friends and offered to let Anna stay on a month-to-month lease until she saved enough to move out.

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Then the housing market went nuts and Anna lost her job (she has gotten another one). It has been over a year. Anna shows no signs of wanting to get going and has even gone on two vacations with her family.

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Any time I bring up the subject Anna shuts it down and tells me her finances are “none of my business.” I am tired of this. This is my home, not hers. I can’t bring anyone over or even explain that my ex has taken over my third bedroom but there is nothing sexual going on.

I am ready to tell Anna she was until the first of September to make her plans because the lease will not be renewed. This is all legal. But I don’t want to spend the next month with a woman on the warpath. Any thoughts?

—Trapped

Dear Prudence, 

I live with my best friend (who is a 32-year-old adult). We are both solidly comfortable in terms of funds (and honestly, though my salary is slightly higher, I have pretty substantive loans/debts that she doesn’t have to worry about). Two years ago, my mom gave me a wine of the month club gift for a month, where you get to mix and match a case of wine for a pretty steep discount. Since then, I buy a case of wine a month because it’s actually pretty economical. I understand that this is a bit of booze, but it’s actually a very useful tool for me in keeping my alcohol intake to a certain limit and it’s cheaper.

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Since I started doing this, my roommate has decided it’s OK to drink my wine, something she did not do when I was just buying one or two bottles at the store at a time. She has never offered to pay me for this because she “only drinks one or two glasses per bottle” so it wouldn’t be fair. I disagree. I have been fairly annoyed by her unwillingness to chip in, and have brought it up a few times, but I do drink more than she does and at a certain point, I can’t be bothered to fight the same fight about her paying even 10-15 percent of something I buy for myself that she treats as an apartment utility. We have been friends for too long to fight about her stealing my booze (or my food, which she also often does) despite how much I hate people stealing my stuff.

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However, I recently bought a few very expensive bottles of wine (like $90-100 bottles) to give as gifts to family members for whom a fancy bottle of wine is the perfect gift. I told her they were presents and stored them slightly separated from the other wine I bought for the month. I went out of town for a week, and she decided to open and drink some bottles of the wine that I bought while I was gone, and drank two of the very expensive bottles of wine. She is refusing to pay me back or buy replacements because “I always share” and she “shouldn’t have had to remember which were special” and I should have kept the gifts far from the “communal wine.”

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The thing is, literally none of the wine is communal, because I am the only one buying it and I have been very upfront both about how (1) those bottles were gifts and (2) I really want her to start paying for the wine or just not drink it. I’m super angry and we had a pretty nasty fight. Am I being unreasonable? Did I train my roommate to walk all over me? Am I being a child because I won’t share? Is my friend being awful? Am I crazy? How can I make her understand that I need her to pay me back?

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—Anxious Grad Student

Dear Anxious,

Yes, your friend is being awful. Actually let me edit that: The person you live with, who is not your friend and is actually a criminal, is being awful. She’s not just walking all over you. Walking all over you would be leaving dishes in the sink or hair in the bathtub. She’s actively, unapologetically stealing from you. This “friendship” is already over, and the roommate arrangement should end ASAP. I’m not saying you should take her to small claims court over some wine, but it wouldn’t hurt to make her think you might…

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Dear Prudence Uncensored

I don’t think I’ve ever met someone who is this shameless!

Jenée Desmond-Harris and friends discuss a letter in this week’s Dear Prudence Uncensored—only for Slate Plus members.

Dear Prudence, 

Six months ago my husband and I went through the worst pain imaginable. We lost our daughter who was stillborn at 37 weeks from a true knot. Fast forward to the weekend of July 4th, my father-in-law, Mike (not his real name) told me that he knew something was going to eventually happen because I kept having children. (Our daughter was baby number six.) He said that he told my MIL that he “knew she would die” and that if I had any more children the same would happen to me. I was dumbfounded and in complete shock as to what he had said. Mind you, this was just three months after we buried our daughter. My husband said, “He’s not the smartest man,” and to brush it off the best I could. My question is, would it be wrong of me to hide a pregnancy from my in-laws? My husband and I would love to have a rainbow baby, but I wouldn’t want anyone to know for as long as possible, especially since going through the loss of our daughter.

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—Faith

Dear Faith,

I am so sorry for your loss. You can hide the pregnancy and the child itself from these heartless people for as long as you want. Seriously, whatever it takes to get you through your next pregnancy as mentally healthy as possible. If they find out the baby exists at their high school graduation when you are finally comfortable, so be it.

Dear Prudence, 

My 15-year-old daughter is a really good kid, and I’ve tried to respond to her various experiments with identity in a spirit that’s curious and nonjudgmental, but her latest one has me stumped. Every day, she paints half of her face purple using stage makeup. When this first started a couple of weeks ago I commented that it was an interesting look and asked about it, and she just shrugged and said she liked it. I’ve mentioned it a couple of times since then and she just says it’s not a big deal and acts like I’m weird for asking about it. I’ve been getting questions from other parents about this and I don’t really have anything to tell them. Is this some kind of internet thing that I’m missing? Is she trying to bait me? Her older brother’s wedding is coming up and he and his fiancé think the whole thing is hilarious, but I’d really prefer she not wear it there.

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—We’re Not Aliens

Dear We’re Not Aliens,

I have no idea what this is about. (Calling all readers who know about internet things that I and the letter writer might be missing! Let me know.) Purple stage makeup kind of crosses the line from “self expression” to “costume” so I think you’d be within your rights to ask her not to wear it to a wedding. But if the bride and groom think it’s hilarious? You’re in luck! Let her paint herself to her heart’s content and save your parenting battle for something that is actually causing her or someone else harm.

Classic Prudie

After we divorced, my ex-wife kept using my last name. We’d married young and her professional reputation was built with that name, so it made sense. It is a small town, so I’m occasionally asked if we’re related, but it’s not too bad. I’m going to be married to a woman who wants to take my last name and has a fairly unusual, culturally specific first name—think “Gretel.” So she’s now going to be Mrs. Gretel [Myname]. Except my ex has, apparently, recently changed her first name….

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