Dear Prudence

An Immodest Proposal

Would it emasculate my boyfriend if I asked him to marry me?

Mallory Ortberg
Mallory Ortberg.

Photo by Sam Breach

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Dear Prudence,
My boyfriend and I have been together for five years and started living together six months ago. He is amazing and I know that I want to spend the rest of my life with him. While shopping, I found the absolute perfect ring for him and have thought about proposing to him. I brought this up to my best friends thinking they would be excited and instead they told me not to. They said I would be “taking away his moment.” He’s not the type of guy to care about the woman proposing but now it has me rethinking things. Do I just continue to wait around for him to propose, or do I plan something nice and go along with my plans of proposing to him?

—On a Ring and a Prayer

Here my personal prejudice will show a little! In general I think it is much more sensible for a couple to agree to get married after discussing it than it is for one to ask the other to make a decision on the spot. Less exciting, maybe, but it also reduces your odds of hearing “Oh … thank you so much, but …” while you’re down on one knee with a ring in your hand. That said, you surely know your boyfriend better than your friends do. If you don’t think it’s important to him that he be the ring-pitcher and not the ring-catcher—and if you feel reasonably certain the answer will be yes—go ahead and propose! The point is not to care who flings a finger-circle at whom. The point is for you two to be happy together and want to get married, which is a lovely thing. Congratulations!

* * *

Dear Prudence,
At my last party, a very good friend of mine who is obese broke a chair as she sat in it. I played polite hostess and made sure she was OK. I’ve now taken it to get fixed and found out it’s broken beyond repair. It’s one of my favorite chairs and can’t be replaced. I’m frustrated! My friend doesn’t make a lot of money, so I don’t feel comfortable asking her to pay for it. She hasn’t mentioned it since. My girlfriend doesn’t want me to say anything. Is there any way to say, “I can’t fix the chair, I have to get a new set, I’m miffed, but ultimately, a chair is just a thing and I care more about you and your health. Can you please take care of yourself?”

–Chair Beyond Repair

I don’t believe there is! Your speech will not be giving her any new information. She knows how much she weighs. She knows she broke your chair. She has not brought it up since then because she is undoubtedly mortified. I understand it’s frustrating to lose a favorite piece of furniture, but imagine how painful it must have been for her in that moment, to fall and them to have all eyes trained on her. If someone falls in your house—no matter what size they are—you make sure they are OK not out of grudging obligation, but because you want to make sure they are OK. I believe that what you really want is to make sure she feels miserable, ashamed, and in your debt. You are angry about the loss of your chair and feel that she has not been embarrassed enough. Since she can’t pay to replace the chair, you would like her to pay you in humiliation. Let the chair go, and resist your desire to remind her of it.

* * *

Dear Prudence,
My first husband died after a long illness; for the last eight years of his life we were essentially co-parents and close friends. After he passed I began dating again; in the two years since I have gotten happily remarried. My daughter loves her stepdad and new relatives. My brother has never met my new husband and refuses to allow him in his house or meet his wife and children. Everyone who has met my husband (even my first husband’s relatives!) adore him. My brother and his wife think I and my daughter should still come over for their children’s birthdays (and bring presents). But they think I’m being unreasonable for refusing to set foot in their home until my husband is welcome. Should I suck it up and go see them without my husband? Or should I stand my ground?

—Punished for Remarrying

Stand your ground. Your brother and his wife are behaving outrageously. Forbidding your new husband from visiting their home won’t make your first husband come back. It won’t even make you any less married now. It’s a bizarre and deeply unloving choice of them to make, especially considering your first husband’s own family have already welcomed your new husband. Hopefully it won’t be too long before they realize how unreasonable they’re being, but until then, the loss is theirs, not yours.

* * *

Dear Prudence,
My long-distance boyfriend of seven years broke up with me this fall. I don’t want to get back together with him, but he handled the breakup badly (canceled a visit at the last minute, then ended things via text). We haven’t spoken since. However, I have a lot of things of his that I’d like to return; items he left in my care with the assumption that he would get them the next time we saw each other. Would it be rude to ship the items back to him? Do I include a note? I hate looking at that stuff in my closet and want to be rid of it, but he behaved terribly and we haven’t spoken in over two months. Is it time to just pack the box off to Goodwill?

–Stuck With Someone Else’s Baggage

Shipping his stuff back to him is the most generous possible thing you could do! No note necessary. Mailing painful trinkets back to a thoughtless ex is a horrible rite of passage, and one that will make you feel fantastic once you’ve gotten rid of them.

* * *

Dear Prudence,
My dad recently seems to have developed a hatred for overweight people that I can’t understand. He says things like “look at this fatty” when we’re out driving. My husband and I object when he says these things, but it doesn’t seem to make a difference. What’s even worse is that my mother is overweight. He says these things around her, and she doesn’t say anything! I think my dad is trying to be funny, but no one laughs. When I came home from the hospital two days after my son’s birth last year, he made a comment about how I “still looked pregnant.” I’m not sure if I should bring it up or just let it be between my parents, but the whole thing really upsets me.

–Unfunny Father

“Look at this fatty” isn’t a joke. It’s barely an observation. I will never understand why so many grown people think the appropriate response to seeing someone fat is to say something cruel. How awful that your mother feels so defeated around your father that she stays quiet when he derides people who are similarly overweight, knowing full well that she will take the insult as intended for her. If you’re otherwise close with your father, consider pulling him aside and asking him why he’s taken to pointing out and insulting fat people. What’s he getting out of it? Why is it so important to him all of a sudden that he audibly passes judgment on how total strangers look? You and your husband are performing a valuable act by speaking up when your father disparages strangers’ appearances. Keep doing it.

* * *

Dear Prudence,
I have a good friend who struggles financially. He keeps his rent money in a PayPal account; every month, his sister withdraws the amount of his rent from her own account and delivers him the cash, and he sends her the PayPal amount. When his sister can’t for some unforeseen reason, I get calls asking me to do it. He says it’s to prevent his bills from being auto-withdrawn from his rent amount, but I find the whole situation weird. Once, he didn’t ask, he just sent the money via PayPal and begged me to get it to him that night. He has a habit of assuming I will do him favors without asking, which bugs me like crazy. But I don’t want to be responsible for him losing his housing (especially since he was homeless briefly this year).

–Last-Minute Banker

I have a lot of sympathy for anyone who lives in fear of homelessness, but I’m not quite sure I understand why your friend needs this strange system to pay his rent every month. If he didn’t have enough money to keep a checking account open, that’s one thing, but it sounds like he just doesn’t know how to turn off auto-pay. Tell him you care about him and you’re willing to help out when you can, but he can’t regularly expect you to drop everything in the middle of the night to deliver bundles of cash for him. It will be better for everyone if he can figure out a more reliable—and simpler!—method of paying his rent on time.

* * *

Dear Prudence,
The last time my husband’s brother and his family were visiting, my husband scraped his brother’s car with his, causing minimal paint damage. My brother-in-law asked us to get repair quotes; the bumper would have to be pulled off and repainted entirely for over $700. My husband wasn’t thrilled, but it was his fault, so we sent a check. My in-laws cashed the check but then decided not to fix their car, which is a work vehicle, since “it’ll probably just get more dings and dents.” My husband is furious and wants them to give us our money back. I don’t think that’s necessarily the right answer, but I’m at a loss.

–Twice Dinged

Your husband did the right thing paying for the cost to repair the scratch, which his brother took as an excuse to take advantage of him. If Bro had always planned to cash your husband’s check without getting his car fixed, odds are he won’t return the money even if you ask. But it’s worth asking. Your husband should tell his brother (as calmly as possible) that he gave him the check with the understanding that it would repair the car, not because he wanted his brother to have $700. If they still refuse to send back a check, you’ll know not to write them any more in the future (and to park on the other side of the street whenever you see them coming).

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Dear Prudence,
After my mother’s recent death I received an email from my cousin “Jane” apologizing for how horribly she had treated me when we grew up together, and saying how wonderful and generous my mom had always been to her despite this. But in fact, when we learned she was dying, my mother apologized for how she’d stood by and let Jane bully me relentlessly. She said she hadn’t wanted to be “one of those parents” who always favored their own child.

Now my mom is gone. I forgave her, but I’m not sure what to do about Jane. Since college I have tried to comport myself around her with civility, but having her admit she knew how horrible she’d been has made things worse. We rarely see each other. I could easily ignore her for the rest of my life without creating any family tension (we have a very large family). Would that be wrong?

–Forgive, Can’t Forget

No. Jane may have apologized, but you’re under no obligation to accept. It’s a good thing for her own soul that she is sorry for what she did, but it does not necessarily follow that you must have a relationship with her. If you have no interest in revisiting your childhood with the woman who did her best to make it as painful as possible, don’t force yourself to. Do what will bring you the most peace. It took her many years to finally reach out to you; there’s no reason she can’t wait many more for a response.

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