Dear Prudence

Deathbed Affair

Prudie advises a woman whose husband is sleeping with his best friend’s wife—while his friend is dying.

Mallory Ortberg
Mallory Ortberg

Sam Breach

Mallory Ortberg, aka Dear Prudence, is online weekly to chat live with readers. An edited transcript of the chat is below. (Sign up below to get Dear Prudence delivered to your inbox each week. Read Prudie’s Slate columns here. Send questions to Prudence at

Readers! Ask me your questions on the voicemail of the Dear Prudence podcast. Just leave a message at 401-371-DEAR (3327), and you may hear your question answered on a future episode of the show.

Mallory Ortberg: “When the time shall arrive for the world to be brought to an end, that it may begin its life anew, all the forces of nature will perish in conflict with one another, the stars will be dashed together, and all the lights which now gleam in regular order in various parts of the sky will then blaze in one fire with all their fuel burning at once.” Let Seneca reach out and bless you on this strangely lit day.

Q. The husband of my husband’s mistress is dying, and I’m stuck: My husband Mike’s lifelong best friend Luke is dying of cancer. He was diagnosed 18 months ago, and he quickly became dependent on his wife Lucy’s care. Mike often pitched in too, spending the occasional night at their house and acting as a father figure to Lucy and Luke’s three young kids. I just found out that for the past year, Lucy and Mike have been having an affair. After Luke passes, Mike will divorce me and, in an appropriate amount of time, marry her.

I’m devastated and torn about what to do. Obviously telling Luke would be cruel, so I don’t plan on that—but if there’s any hope of saving my marriage, I need to act sooner than later. I don’t even know if I want to do that, and I have no idea what to do. For what it’s worth, as betrayed as I feel, I don’t think Mike or Lucy wanted this to happen.

A: It must be incredibly difficult to process the end of your marriage as well as the death of a close family friend. Your decision to spare Luke from this pain and bewilderment in the last months of his life is a good one, but that doesn’t mean that you can’t make decisions about your own marriage in the meantime.

You say you want to act if there is “any hope” of saving your marriage, but you also know that Mike is already planning to marry Lucy after her husband dies. Your husband did not have a momentary lapse in judgment nor does he appear to regret getting involved with Lucy. It would be one thing if he wished to reconcile and you wished to forgive him, but by all accounts, he intends to spend the rest of his life with her. I encourage you to find a therapist you can trust to process all of this information, talk to some of your trusted friends and lean on them for support, and consult a divorce lawyer.

You don’t have to rush into anything you’re not ready to do, but you should look out for yourself. Mike and Lucy are taking care of themselves, and Luke is being cared for—make sure someone is taking care of you.

Q. You’re not invited: I’m a wedding officiant and have noticed a lot of rubbernecking at weddings. Some of the couples I marry opt for a simple elopement ceremony with a couple friends, or family members, or sometimes none at all. They pick local beautiful parks for the ceremony site, and we find a quiet corner to do the ceremony. My issue is with the people who take it upon themselves to become guests or audience members. At one wedding, people plopped down on the grass and started recording and taking photos. What was supposed to be an emotional, intimate moment for this couple turned into being looked at like zoo animals. The bride felt embarrassed about crying and getting emotional with all these people watching. I’ve also had people come up after the ceremony to gawk at the couple or to make small talk that just ends up being awkward and unnecessary. And then there are the people who stand super close to the ceremony site and end up in the photos.

I understand glancing at the ceremony as you walk by, but I can’t imagine stopping and joining in like this. I know it’s a public park but there should be at least a base sense of privacy and decency. Am I being too harsh on these rubberneckers?

A: No, that’s definitely inappropriate! In the future, since you’ve noticed this has become a pattern, you should speak to the couple getting married and ask if they want to assign a member of the wedding party to act as a (polite) bouncer. That doesn’t mean you have to start chucking Frisbees at anyone who wanders too close to the ceremony, but someone on Rubbernecking Duty could politely inform strangers taking pictures or wandering directly into the aisle that they should move on.

Q. Do I have to be a patron to be a friend?: I have a friend who’s an artist. I love hanging out with him, and he’s definitely skilled. He doesn’t have a traditional job right now because he’s trying to make his living on art, which I think is great. Problem is, he depends heavily on friends to buy his stuff and share his work on social media. I’ve commissioned him a few times and share his art sometimes. I want to support him when I can, but he always seems frustrated that people in his friend group aren’t supporting his work more. Is this something I can address? I don’t want him to resent me.

A: You’re his friend, not his employer or his mentor. It’s lousy to make your friends feel responsible for your success or failure as an artist, and if your friend resents you for not buying one of his creations every month, then he has unreasonable expectations of his friendships. That sort of pressure-filled leveraging of social relationships to make money is a killer of friendships. (Ask anyone who’s lost a loved one to an MLM company.) Counting on everyone you know personally to endlessly buy your work is not a sustainable career path for an artist.

If he tries to make you feel guilty, either directly or indirectly, for not permanently sponsoring him, you can and should push back. Tell him you love him and want him to be successful—and have often offered him financial support in the past—but you’re his friend, not Lorenzo de Medici, and he can’t hold his friends responsible for his career choices.

Q. Whether or not to have kids: I am a 41-year-old woman married to a 31-year-old man. We love each other very much. He is a warm, loyal, intelligent, and kind man. He would be an excellent father. I have been told often that I would make an excellent mother.

However, I was extremely ill for many years with an autoimmune disorder and have only recently recovered. We had originally resigned ourselves to not having kids and using our “parenting” powers by being positive examples and influences in our niece and nephew’s lives. Now that I am recovered, we have a short window of time while I am still fertile to have kids. I am scared that it will throw me into a relapse, but I also know that this is my last chance.

Both of us are on the fence. We don’t know what to do. I love my husband, and I worry that he is still so young he may wake up one day and have regrets if we don’t have children. But my body is still exhausted and I am afraid of childbirth. What is the wisest course of action?

A: Talk to your doctor. I don’t know what the odds are that getting pregnant will negatively affect your health, but you should absolutely bring up your concerns with a professional who’s familiar with your medical history and learn more about the risks you face.

Only you can decide whether the potential rewards outweigh the risks, or whether parenting without having biological children is an option for you, and you should gather as much information as possible before making any calls. It’s possible to have a good, happy life both with and without children.

If it’s at all helpful, I think it’s better to make a decision about this based on your current health, abilities, and desires rather than the possibility that someday your younger husband might have regrets. You can’t live in that possible future. You can only live the life you have now.

Q. Wine whine: About two years ago, I started brewing wine as a hobby. I’ve gotten decent at it and have been giving bottles out as gifts for about a year now. Recently, on Facebook, a cousin was talking about his struggle with alcoholism. I sent him a bottle as a wedding gift months ago! I truly had no idea! Now I’m not sure if I should apologize to him, and I’m also not sure about future wine gifts. Should I clear this kind of gift before sending? Not send the wine at all? I’m really not sure here.

A: You did not do anything wrong! Get in touch with your cousin and tell him you’re proud of him for his honesty and that he has your support. Don’t send him any more wine. Continue to send wine to other people in your life.

Q. Office romantic: Is it ever a good idea to date a co-worker? Right now, it’s just a little crush. We don’t work in the same department and barely interact on a work basis just to have lunch together. (I work for corporate and he works for the branch location, but we’re in the same office.) Even so, friends have said don’t do it because we are in the same office. Like I said, it’s just a crush, so I have no idea if he is even interested in me. There’s no policy against it in my company and I’ve seen others enter relationships. Because of that I’ve seen a lot of awkward aftermath.

This is my first job out of college, I’m not sure what the norm is. Is it ever a good idea to date where you work, or should I just keep fantasizing?

A: It definitely happens; that’s part of why so many companies have specific policies about disclosing romantic relationships to HR and ensuring they won’t interfere with the chain of command. There’s certainly a higher potential for pain and embarrassment if things don’t work out, but depending on the type of office you work in, you might become quite close with your co-workers and get to know them extremely well, which can make getting into a relationship look a lot more appealing. It doesn’t sound like you two are anywhere near asking each other out, so feel free to enjoy this for what it is—a crush on someone you see around the office every once in a while.

If anyone has dated a co-worker and wants to share their experience, for good or for ill, feel free to make a recommendation in the comments.

Q: Re: The husband of my husband’s mistress is dying, and I’m stuck: You need to ask the wife of the cheating husband if she has kids. I think that’s important to how you answer.

Mallory: Whether or not they have children together will certainly affect how things go from here, but at a certain point, the fact that her husband already has plans to marry his mistress after her husband’s death trumps all. If he’s already organizing his next marriage in light of his best friend’s impending death, then reminding him that they have children together isn’t likely to change his mind.

Q. Should I continue this friendship?: “Katie” has been my best friend for five years. I have enjoyed being friends with her, but she tends to be overly critical of people she’s close to. For example, she’s criticized facets of my appearance, my decision to date certain guys, and even my choice of program for a postgraduate degree.

We now live in different cities and hadn’t seen each other in months until we took a trip together recently. During the trip, all of my previous frustrations with her came up, and we had some pretty big arguments. I realized I did not care to be her friend anymore.

Since I’ve been back from the trip, I have been trying to slowly fade out from the friendship. However, I feel guilty because I don’t want to abandon our friendship, especially without first having a conversation with her. I don’t know if a conversation would be very productive though because before when I’ve tried to tell her she’s being too critical, she has said that as a friend, she has the right to tell me her honest opinion on my life and choices.

I also know that she’s currently having a hard time with different things in her life, and I don’t want to make her feel even more isolated. But I’m still pretty hurt from the things she said on our trip. I have been in therapy for a while dealing with my tendency to let people treat me badly in relationships, so I don’t want to go back on that work by letting her continue to be a critical presence in my life.

Should I continue to be friends with her? Should I have a conversation with her about my feelings or continue the slow fade out?

A: You’ve already had multiple conversations about this topic, and they’ve turned into arguments where Katie has reaffirmed her commitment to criticizing you under the guise of friendship. It can be important, albeit painful, when a good friend suggests one needs to re-examine one’s behavior or choices, but that’s not the same thing as tearing down someone else’s appearance or career choices.

I think it’s worth telling her that you need a break from talking for a while and that you’re not looking for constant criticism from your friends. If she sees that as an integral component of the very nature of friendship, it may simply be impossible for the two of you to continue as you are. If she demonstrates any ability to hear your point of view, or a desire to slightly modify her relationship to censure, then you might be able to find a way forward after a time. If she doesn’t, then you’ll know you didn’t just give up on her without trying.

Q. Re: The husband of my husband’s mistress is dying, and I’m stuck: I say this as a mistress of a married man myself (just mentioning for context, and I can sympathize with your husband, Lucy, and Luke), but you need to think of yourself here. If your goal is to fight for your marriage, go nuclear. Tell Luke despite the pain it will cause. Blow this thing up. It might already be too late, but you will know you tried.

Q. Eclipse: Should I stare directly at it? I’m torn.

A: I want to look at it directly more than I’ve ever wanted anything in my life. I finally understand Lot’s wife. But, you know. Don’t.

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