Dear Prudence

I Dumped My Ex-Boyfriend Four Years Ago. He’s Still Living With Me.

I want him gone, but I don’t have the heart to throw him out on the streets.

Hands tearing apart a photo of a couple in front of a silhouette of a house
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Dear Prudence,

I have been dating a man now for eight years who is a loving, awesome person in many ways. He adores me, and he treats me like a queen. The problem is that I don’t want any of it anymore. He struggles with alcoholism and anxiety, cannot hold down a job, and still lives like a college student just scraping by, despite being in his 40s. I decided four years ago that he’s not what I’m looking for, as a divorced mother of two, despite his many good qualities. But because of all these issues, mainly that he has no money, he still has not left my space.

He lives in denial and treats our relationship like we are mutually involved when he knows exactly how I feel. I want him to move out, and it always comes down to the fact that he has no money and really can’t get another place in our ridiculously expensive town. I don’t have the heart to throw him out on the streets, and he does not have a single friend who would let him move in due to his history with drinking. He goes to a therapist, and he says he understands and doesn’t want to hold me hostage in this relationship, but it just does not stop. I don’t want to live with resentment and anger toward a dependent person who obviously cares more about his own self-preservation than releasing me from the relationship I no longer wish to be a part of. I have said and done everything short of changing my locks and physically restraining him from my home (which I just cannot do). What can I do to finally initiate change?

—Roommates Forever

You have things backward, I fear. You say you can’t kick him out because then he’d be completely helpless, when I think he’s completely helpless because he knows you will never kick him out. You do not need him to “release” you from this relationship, because breakups do not require a unanimous vote. Presumably he managed to keep body and soul together before you two started dating, so I don’t think it’s unreasonable to believe that he’d find a way to continue living if you two ever really broke up. If you really want to move on, you’ll have to let him solve his own problems again (or fail to solve his own problems, or find another girlfriend to solve them for him, as the case may be). But that will require letting go of the fantasy that he’s absolutely dependent upon you, that you’re the only thing standing in between him and the streets. He’s proved fairly ingenious at finessing his way into a rent-free living arrangement with his ex-girlfriend for the last four years! You must give him at least a little credit for resourcefulness. I wonder, if he’d applied some of that resourcefulness elsewhere, if he might have found one or even two possible alternatives, even in your very expensive city (or a less expensive city).

You can even offer to front him first and last month’s rent, if you just want to throw money at the problem. I do worry that once you start giving him rent money, you’ll never stop, but you’re already paying his rent now, and at least in that scenario you get to have your bedroom back to yourself. Another option is to consult local tenant laws, then evict him. If you can’t bring yourself to change the locks, hire a locksmith to do it for you, a moving company to put his stuff neatly into storage, and a claim ticket so he can pick it up at his earliest convenience. If that sounds as daunting as trying to walk to the moon, consider attending a few Al-Anon meetings to see if you can find solidarity and support there. But there’s nothing cruel or unusual about telling your ex-boyfriend he can’t live with you forever. Your distress and concern are readily apparent, and I am sorry you’ve been suffering over this decision for so long, but you already know that nothing about this situation is going to change until you decide to do something different. If you simply can’t bring yourself to kick your ex out, then prepare yourself to live with him for the rest of your life. He seems perfectly content to be your roommate and your dependent, forever.

Help! My Wife Is Too Stupid to Home-School Our Kids.

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Dear Prudence,

I have had an on-again, off-again fling with an older man for about a year and a half. Right now, we are at a place of hooking up once every few months. He likes to be rough, and for the past few times, it’s been a problem. He likes to have anal sex, and he’s the only person I’ve done it with. He doesn’t want to use lube, and so every time, I’m left sore and sometimes bleeding for a few days afterward. One of the last times, it hurt a lot, and I said no, but he didn’t stop for a few seconds, until I started crying. The next time, he was very apologetic when I told him he hurt me. But a couple of nights ago, he told me he still wants to have anal sex because that’s pretty much what he thinks about when he thinks about me. I kept saying no and resisting all night. But it got to the point where giving him a blowjob really messed with my gag reflex, and he told me anal sex would make him come faster. I agreed, but it was again painful, so I said no, and he again didn’t pull out immediately, saying, “Just a second more.” The whole thing left me feeling frustrated and angry at myself that I didn’t enforce respect for my body. I kept telling him he needed to respect me, and I don’t think he took it that seriously because he said I had always enjoyed anal in the past (I didn’t). He also said he likes the feeling of me being helpless under him, which I told him feels creepy. He’s also told me on multiple occasions that I’m fat and I don’t try hard enough because I don’t shave my body hair. I hate that I keep letting him come over. I guess I just need validation that this might be an abusive situation with sexual assault, and that I absolutely should not give him another chance. I wish I could handle anal. I wish I could be cool about the rest of it. But I can’t.

—Not Just a Bad Date

It’s not that you can’t “handle” anal sex—it’s that this man enjoys hurting you and wants to see you in pain, self-conscious, insecure, and as confused about whether he heard your last “no” as possible. He’s sexually assaulted you repeatedly. You do not have to be cool about that. You did not invite or deserve his assault, and you shouldn’t have to think of a date as a minefield where you have to be constantly on high alert, vigorously defending and enforcing your boundaries from a hostile agent bent on undermining you. If someone says to her date, “You’re hurting me, and you need to respect me,” and he ignores her, tells her what she really likes, and continues hurting her, the fault is not hers for being hurt, but his for deliberate cruelty.

I don’t want you to berate yourself for letting him come over. You wanted to have sex with the man you were seeing, and you hoped to be treated with basic respect and kindness when you slept with him; you wanted to believe he was willing to listen and take your needs into consideration. You have nothing to be ashamed of on that front. He does not deserve another chance from you. He did not hurt you on accident, or because he was confused, or because you were insufficiently respectable, but because he wanted to and because he liked it. Remember that you do not have to do anything you don’t want to, but you do have options available to you, up to and including pressing charges. If you don’t yet feel prepared to turn to your friends for support but you need someone to talk to, you can always call the National Sexual Assault Hotline at 1-800-656-4673.

Dear Prudence,

“C,” my grandfather’s second wife (who was 26 years younger than him) died recently from coronavirus while in residence in a nursing home. Her daughter and other family members made the decision to move her near them about eight years ago so they could visit her more easily. My aunt, the youngest of my grandfather’s five children, took it upon herself to publish the official obituary of her stepmother in the original city where we all come from and also posted it on Facebook. The problem lies in the fact that there is no mention of the woman as a stepmother. My aunt listed all her sisters and brothers as C’s progeny, despite the fact they all are either the same age as C or older. She also listed every one of the grandchildren and great-grandchildren as being related to C. Needless to say, several people in the family are very upset and have asked for her to rewrite the obituary. She did mention C’s biological daughter and grandchildren in the obit, but the wording put much more emphasis upon the large family she married into, rather than C’s biological family. Are we wrong to think the information is false and misleading?

—Frustrated Over Finalities

You may not be wrong to be annoyed at an obituary that doesn’t distinguish between biological parents and stepparents (especially if C married your grandfather after his children were mostly grown and out of the house), but I wonder if there’s an opportunity to let something go here. You don’t say anything about your own relationship with C, whether you were close or indifferent, whether you liked her or found her a nuisance, whether you visited her in the home before she died or preferred the distance of the last eight years. I imagine there might be some clues there!

Some of your relatives have already asked your aunt to rewrite the obituary to be more clear. If she agrees, then that’s all there is to be said on the subject. If she declines, one of you might decide to write one of your own (even just an unofficial one on Facebook). But in the grand scheme of things, C will still be dead, and everyone who knew her will still be perfectly aware of whether she gave birth to them, or raised them, or married their father when they were in their 30s, or whatever their relationship happened to be. It doesn’t sound like your aunt was demanding her siblings all call C “Mother” at the funeral, simply that she wanted to acknowledge their blended family without distinction. If you all collectively decide to let this one go, nothing will happen. No one will be forced into a relationship with C that they don’t want to have, and no one will be confused about their own parentage or disinherited. Most people will never read this obituary, and those who do will quickly move on to the business of living—a sad, but in this case convenient, fact about death.

Catch up on this week’s Prudie.

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Classic Prudie

I live in one of the wealthiest neighborhoods in the country, but on one of the more “modest” streets—mostly doctors and lawyers and family business owners. (A few blocks away are billionaires, families with famous last names, media moguls, etc.) I have noticed that on Halloween, what seems like 75 percent of the trick-or-treaters are clearly not from this neighborhood. Kids arrive in overflowing cars from less fortunate areas. I feel this is inappropriate. Halloween isn’t a social service or a charity in which I have to buy candy for less fortunate children. Obviously this makes me feel like a terrible person, because what’s the big deal about making less fortunate kids happy on a holiday? But it just bugs me, because we already pay more than enough taxes toward actual social services. Should Halloween be a neighborhood activity, or is it legitimately a free-for-all in which people hunt down the best candy grounds for their kids?