Dear Prudence

Permanently Casual

I’m 30 and never want to give up Tinder. Is something wrong with me?

Mallory Ortberg
Mallory Ortberg.

Photo by Sam Breach

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Dear Prudence,
In college, I started having a series of flings and casual sex with no consequences. I never had an issue with it and neither anyone else in my life. I’m now 30 and I’m still hooking up. I love Tinder. The trouble is, now that I’m older I’m getting a lot of judgment thrown at me. My sister says I need to find a nice guy and settle down. My friends say variations on the same theme. I’m OK with things the way they are. I doubt I could settle into monogamy anyway, and I’ve never really wanted kids. Last night, I told my sister that, and she said I’d better get my act together or I’d be too old for a “real” relationship and would have to settle. So I’m wondering—can you get too old for casual flings? Do real relationships have a sell-by date?

—Too Old for Flings

Your sister is afraid of ambiguity and, by extension, death—both her own and that of the people she loves. (Hear me out. I promise this is going somewhere.) Monogamy during prime childrearing years is a cultural norm that often results in increased social status, state-sponsored recognition, and financial rewards, and in that regard it makes sense, on a nominal level, that your sister would want that for someone she loved. However, her insistence that you must pursue something you have said you do not desire can only come from a compulsion to see everyone around her settled in a long-term, reproductively viable relationship so she can feel that her life, and the lives of her family members, will stand as a bulwark against the forces of chaos. The only kind of romantic relationship she can accept as “real” involves exclusivity and permanence—a rather narrow definition. So that’s your sister.

But—here is the crucial point—you do not want to be in that kind of relationship. There is no magical age that will require you to pursue this kind of relationship, just as there’s no magical age that would prevent you from one day doing so, particularly since you don’t want children, and there is no earthly reason you should have to “settle down” simply because you might someday, according to your sister, become too old to experience romantic love. No such expiration date exists.

* * *

Dear Prudence,
My boyfriend and I have been dating (monogamously, but casually) for over a year. A few months ago, he (virtually) cheated on me with a girl at work. They sent each other explicit photos and videos, although nothing physical happened. He’s apologized, and we’ve moved on—but the photos haven’t. I usually subscribe to the idea that your nudes are your business—I would like to look back on my deathbed at all the nudes I have ever enjoyed and chuckle quietly. However, I think that the infidelity makes this a different situation. Am I within my rights to ask him to delete them, even though we both know that our relationship isn’t forever?

—Can I Ask Him to Delete His Nudes

You ended on such a fascinating but unexplained note! How do you know this relationship is temporary? If you’re planning on breaking up with him, why not just do it now, and let him enjoy as many nudes as he wants? There are mysteries within mysteries here (one being, how are you so certain nothing physical happened?), but I’ll restrict myself to the question you gave me: You are free to ask him anything. Don’t demand it as an ultimatum, but tell him you’d appreciate the gesture. You’re hardly asking too much of him; he can send and receive countless nudes to and from anyone he likes after your preordained split.

* * *

Dear Prudence,
My boyfriend and I have been together for several years and recently started living together. We both have well-paying jobs and we’d like to get married someday. The problem is my younger brother. He’s 23 and very smart, but he’s lazy, disrespectful, and a slob. He dropped out of college after a semester and has lived in my parents’ basement ever since, relying on them for everything. He also spent most of my childhood making the lives of my sisters and myself hellish whenever we were home: He shoved us around, insulted and mocked us. My parents are elderly and will likely be moving into an assisted-living facility in the next few years. They have two lovely dogs that my boyfriend and I have agreed to take in when that happens (we’re huge animal lovers), but for the last year or two, my parents have been making noises about my brother’s living with us or one of my sisters. I refuse to spend the rest of my life providing for and cleaning up after a lazy jerk, and my sisters feel the same way. The three of us worked hard and were entirely independent by our early 20s; we are happy, functioning adults with good relationships with our parents and each other. We’re all worried that announcing “little brother needs to get a job and provide for himself, because he’s sure as hell not living with any of us” will strain our relationship with our parents (whom we love). Do you have any advice?

—Yes to the Dogs, No to the Brother

The problem right now is that your parents have been creating a vague expectation (“making noises”) that one of you will take in your brother rather than making an outright request that could be met with a definite “yes” or “no.” The situation lacks clarity, and will stay that way as long as no one comes out and states exactly what it is that they want. Provide that missing element now, because this is an inevitable conversation that should not be delayed until the day your parents move into a nursing home and you feel overwhelmed with guilt. If saying “My brother can’t move in with me after you move into assisted living” will strain your relationship with your parents, better to go through that strain now than when they are perhaps incapable of having difficult conversations. Surely, too, it’s better for your brother to have no illusions about his future, and knowing now that he has a limited time to find a job and a place of his own will only benefit him in the long run. Drop the “sure as hell” part of your proposed speech and you have, in fact, a perfectly reasonable and gentle statement of intention.

* * *

Dear Prudence,
My wife and I have been married a long time. I recently found out that there is a very good chance she slept with her ex back when we were dating. My inclination was to let sleeping dogs lie, since that is long past, but I am good friends with her ex’s brother, and we have close mutual friends who I think are aware of this fact. If true, this issue is in no way a deal-breaker for us; I believe it will clear the air if she confirms this and I will offer that I would like not to be the only one who does not know about this. My concern is, will bringing it up at this late date cause more harm than good? I believe I can let it go without mentioning, but it will not be easy to do so. Thank you in advance for your help.

—Statute of Limitations

It can be quite difficult to start a painful conversation with someone you love when you don’t feel like you absolutely have to, and I can feel that reluctance in your letter. “Since I know we’re not going to divorce over this,” the thinking goes, “what’s the point in bringing it up at all?” But there are very good reasons to bring this up—the truth is almost always a good thing to discuss, and you should be able to discuss any issue, no matter how long ago or relatively insignificant, with total freedom, with a loving partner. What truly troubles you, it seems, is the idea that your mutual friends know your wife once slept with her ex. Whether you fear embarrassment, or are bothered that they have always known something about your relationship that you did not, the fact remains that you have been happily married for a long time, and these friends have surely come to believe in the solid and honest foundation of your relationship with your wife.

What you want to do is not to accuse your wife and force her to atone for the act itself, but to have an honest conversation about something from the past that is currently making you feel a bit exposed and vulnerable in the present. That’s a good idea, I think, and I encourage you to pursue it.

* * *

Dear Prudence,
A year-and-a-half ago, my only living son killed himself. His estranged wife had called me to say he was threatening to hurt himself and that I should check on him. I found the body. My only source of light since then is my little grandson. My relationship with his mother is difficult at best: She was the one who wanted the divorce and didn’t want to try and save my son. Now she is getting married again. This stranger will be the one who raises my grandson, gets called Daddy, and might even adopt him. There is nothing I can do legally, and I choke back my words every time I see her when she picks up my grandson from me. Can you think of anything to say that will convince her to stop this?

—Lost Son and Now Grandson

I’m so sorry for everyone involved in this situation, and I’m so sorry that you lost your son. I cannot imagine that kind of pain, and I hope you are in grief counseling to deal with the infinitely complicated and painful fallout from the death of your child. I also hope that you can work out these fears in counseling, because you should not try to stop your former daughter-in-law from remarrying, and she does not deserve to be made to feel guilty for moving on. You say she didn’t “try and save my son,” but you cannot put the burden of his death on her. His suicide cannot be, could never be, her responsibility. The fact that your grandson may grow up with a father who loves him is not a tragedy, but a good thing, and this man is not “a stranger”—he is a stranger to you, but not to the mother of your grandson, and not to her little boy. Please try to find a way to express your pain and sense of loss that does not come at the expense of the woman raising your grandson. Focus on the time you do spend with him, and not on his mother when she comes to pick him up. Read to him, tell him you love him, play with him, take him to the park—let him look forward to the time you spend together, and don’t tarnish it for him by focusing on your resentment of his mother. You will all be better for it, and it will vastly improve your relationship with your grandson and his parents for the rest of your lives.

* * *

Dear Prudence,
About eight months ago I lent $1,000 to a friend. She was unemployed then and needed it for car insurance and some other stuff. A couple of months later, she found a job and paid me back half. Last week, we had dinner together and I was going to ask about the second half, but she told me a) she was out of work again and b) she was getting married and was hoping to get employed again soon so she could save every penny for her wedding in April. I can’t ask for it back now, right? Should I just forget about this money?

Of course you can ask. Say this: “I’m so sorry you lost your job and I understand there are extenuating financial circumstances that mean you can’t pay me back the rest of the loan right now. Let’s find a repayment schedule that works for us both, because I don’t want you to feel you have to avoid me if you don’t have the money right away, and I don’t want to feel like a bill collector instead of a friend.” You could even suggest a payment schedule of some token amount of money per month—$50 or $25—to start when she finds a new job, so that she’s not unduly burdened but can demonstrate she sees you as more than just a bank to be dodged as her financial situation fluctuates.

* * *

Dear Prudence,
I was married for over 20 years before my husband left me for another woman (younger, of course). It was never a good marriage, and I stayed for all the wrong reasons. The past 10 years on my own are the happiest I’ve ever been. I have a great job, a great home, and do what I want, when I want. I am not in the least bit interested in another marriage. My contact with my ex-husband is minimal. We meet rarely at family functions. We are cordial, but no more than that. The last time we saw each other was at our younger daughter’s wedding two years ago.

Last night, my younger daughter called me in tears. Her father is dying: He has cancer and is not expected to live more than six months. His wife left him once they got the diagnosis and is divorcing him. He has nobody to care for him and no money to pay for help. My daughters want me to move in with him and take care of him during his last months. I do not want to. Our marriage was not good:He cheated on me continually, treated me badly, and did all he could to smear my reputation during our divorce. I have no intention of taking care of him. This may make me a terrible human being but I don’t care. My daughters of course both adore him, and never saw him as flawed in any way, so they will not take this decision well. Can you see a way I can tell them without trashing their father?

—What Do I Owe My Ex

At the risk of sounding flippant, I wonder why your daughters, if they are so concerned for their father, do not offer to move in with and take care of him themselves. What’s happened to him is very sad, but it is not your responsibility to become your ex-husband’s nursemaid after a shabby marriage and years of little-to-no contact. Your adult daughters do not have the right to use their concern and sympathy for their father as an excuse for shouldering you with responsibility for his care. You have every right to tell them your marriage to him was not a happy one, that you are not going to take care of him, and that they are way out of line in not just asking, but insisting, that you do so.

* * *

Dear Prudence,
I have an acquaintance from the same theater/performing circles in our city. She barely scrapes by, does not have a car, has severe anxiety and self-esteem issues, and depends on others for many things. We have occasionally met for coffee, just as casual friends and sometimes for work-related projects, and sometimes I give her rides to gigs we’re both doing. On every occasion, she has kept me waiting for what I think is an egregious amount of time—like 30 minutes. She once kept me waiting so long for a gig we were both booked for that we ended up being late. She recently saw on Facebook that I was interested in attending an event that is 45 minutes away, and emailed me suggesting we go together. I do not want to go with her because I get so frustrated at being kept waiting. How do I say no kindly? And what is kindest? To hedge or demure, or to be truthful in the kindest language possible? I want to be compassionate for her struggle, but I’m also trying to have boundaries about something that just sends me over the edge.

—How to Say No

“I’d be happy to drive with you, but I’m leaving at 6 p.m., and if you can’t make it by then, I’ll have to go without you.” Then leave at 6 p.m. This is both kind and firm. You’re providing her with all the information she needs—leaving at 6 p.m. is not a surprise—and offering both a friendly service and a boundary. I say this as someone who struggles with excessive time-and-space optimism herself; sometimes the best thing for us is to miss a few events we really wanted to attend.

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