Dear Prudence

I’m 20 Years Younger Than My Boyfriend. How Do I Get His Teenage Daughter to Like Me?

Prudie’s column for March 21.

Woman looking sheepishly at father and daughter.
Photo illustration by Slate. Photos by iconogenic/iStock/Getty Images Plus and monkeybusinessimages/iStock/Getty Images Plus.

Dear Prudence,
I’ve been dating a divorced man who is more than 20 years my senior for three months, and I like him a lot. I’m meeting some of his friends and his teenage daughter later this week. I’m so nervous about meeting his daughter, especially because I’m closer to her age than his, and he has said that she can be very protective of him. How can I avoid screwing up this meeting? What is the best way to approach his daughter that is respectful and nonthreatening to her?
—Meeting My Boyfriend’s Daughter

Letting go of the expectation that you can control her reaction is going to be your best bet. You might be friendly and relaxed, with a real fun aunt vibe, and she might find the mere fact that you’re close to her age and dating her dad upsetting anyway. The best approach, I think, is to ask your boyfriend a lot of questions and be ready to postpone the meeting until you feel like you’re all as prepared as possible. Has he introduced his daughter to women he’s dated before? How has that gone? What has he told her about you, and how does she seem to be adjusting to the news? What does he mean by “very protective”? While you’re at it, ask yourself if you feel ready to get even tangentially involved in his daughter’s life after a three-month relationship and before you’ve gotten really emotionally invested. If you don’t trust that your boyfriend’s put a lot of thought and energy into planning this meeting, it’s worth putting off. If you decide to go ahead with it anyway, be friendly, and don’t try to wring any particular response out of her. Let her be distant or moody or reserved if she wants, and strive for pleasant neutrality.

Dear Prudence,
My dad is very sick with lung cancer, has a compromised immune system because of chemo, and has terrible gout in his hand. He was recently diagnosed with chronic obstructive pulmonary disease and is often exhausted. My mom has her own medical issues and, by awful coincidence, is having a terrible episode of knee pain that has reduced her mobility. My main worry is that my mom often says things like “Dad will be all right; he’s going to get through this.” My dad has occasionally talked about death and has started preparing me to take over his personal business (paying the bills, taking care of their estate and property, helping my mom out, etc.) if things take a turn. He also will comment to our mom a bit about death, to which my mom has replied, “I don’t want to hear that,” or “He’s going to be fine. I don’t want to hear him talk like that.” Both my dad and I are worried about what seems obvious: He’s very sick with cancer, may die from it, and is preparing himself mentally and emotionally for that possibility. Is it wrong of me to gently encourage my mom to develop a different coping mechanism to help my dad talk or think it through? Should I simply respect that she will have her own process, which may include a long period of denial (maybe never accepting death until it actually happens)?
—Mom in Denial

There’s a limit to how much you can force this conversation on your mother, which I think you realize. She’s dealing with chronic pain and immobility and a very ill partner, so she may feel like she doesn’t have the resources to think about your father’s death right now. It’s good that you and your father are setting aside the time to prepare for the worst, and to whatever extent you’re able to facilitate a smooth transfer of financial and logistical responsibilities without involving your mother directly, you should continue to act on her behalf. It might help, if she seems deeply distressed, to ask if there’s anything else she needs right now to help her manage her pain or get help taking care of the house. It may also help to offer her the chance to be part of this conversation without trying to force her into anything; say, if you and your dad set aside an afternoon to meet with a lawyer and estate planner to go over his will and end-of-life wishes, you can tell your mother about it in advance, ask her to join you if she’s able, but ultimately leave it up to her. You can stress that you’re not giving up: “We all hope that Dad is able to recover, but we want to be prepared for everything, including the worst.” But if she can’t or won’t participate, you shouldn’t push her.

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Dear Prudence,
After my divorce, I began dating a friend of a friend who happened to be down on his luck—divorce, bankruptcy, unemployment. I let him move in because he was otherwise homeless. When he contributed minimally to expenses, I understood his circumstances. We agreed numerous times that he would contribute more as he got back on his feet. We’ve been together for 10 years now, and he still contributes less than one-third of expenses. I make probably a third more than he does, but his dodging makes me feel used and exploited. His monthly rent is equal to what my 23-year-old niece pays with three roommates! How do I get him to understand that he has an obligation to earn his own livelihood?
—Frustrated Enabler

I understand why you feel used and exploited—you have been for the past 10 years. That’s not to say your boyfriend may not genuinely like you—he may!—but since the immediate crisis has long passed, it’s clear that financial parity is not a priority for him. Yes, you make more than him, but not so much more that there’s a huge discrepancy in what you’re both able to afford. It’s been 10 years, and you two have talked about this repeatedly, so I don’t think it’s a case of him misunderstanding the situation. It’s just that he’s learned that as long as he occasionally pays lip service to contributing equally, he gets what he wants out of the situation. It’s time to move from talking about it to taking action. Let him know that you’re instituting a rent increase (check your state laws first to find out exactly how much notice you’re required to give him and how much you’re legally allowed to raise the rent in a single year), effective a certain date in the near future, and that he can either increase his contribution or find another place to live. He should understand it pretty well then.

Dear Prudence,
My older mother uses a lot of medication to help manage her chronic pain. Unfortunately, this means that often I find myself talking with a woman who is under the influence. These phone conversations are very upsetting to me, as I often feel I’m talking with someone who is either losing her mind or cruel. I’ve asked her to not call me when she is under the influence, but still once a month I get a call from her while she’s high on Vicodin, Ambien, or medical marijuana. I don’t want her to be in pain, and in fact I’m a supporter of medical marijuana, but the medications have made it impossible for me to talk with her. A few nights ago, I hung up the phone in tears because of how she was acting. I asked her during the call if she was high and she said no, but in the light of day, I can tell that she was under the influence of something. How can I reconcile her need for pain management with my need to have a relationship with a sober individual?
—Drunk-Dialing Mom

This is a really difficult situation, and I don’t have an answer that will serve in all situations, but it will help from now on to assume that your mother is not always going to be the best judge of when she’s sober enough to call you. That may mean getting off the phone as soon as she starts to wander from the topic or says something out of character, rather than waiting until you’re dissolving in tears. You don’t have to get into an argument with her about whether she’s altered in those moments. Just say, “Mom, I can’t talk to you right now. Let’s talk another time,” and hang up. It may also mean deleting a voicemail without listening to it if she gets angry and calls you back right away or setting your phone to “do not disturb” during certain hours you know she’s usually on her medication. It may also help to attend a few meetings for family and friends of addicts—not that you need to label your mother an addict, but you are experiencing a problem that many of their loved ones face and could benefit from their support. Yes, your mother experiences chronic pain and deserves access to medication that treats it, but that doesn’t mean you can’t set limits about when you’re available to talk to her, and it still hurts when she says cruel things, even if you know she’s not completely responsible for them.

Dear Prudence Uncensored

“There is a reason he’s dating two decades younger.”

Daniel Mallory Ortberg and Nicole Cliffe discuss this letter in this week’s Dear Prudence Uncensored—only for Slate Plus members.

Dear Prudence,
I work in a high school. “Alex” and I sometimes socialize together, while “Byron” is friendly and gets on well with everyone but is married and doesn’t socialize much with other teachers. Last week, Alex revealed to me that about four months ago, Byron had asked for a loan of about $5,000 until next payday. Byron never repaid it, and every payday since, Byron has approached Alex and said he doesn’t have the money this month. Alex now feels foolish for lending the money. Two days ago, Alex emailed Byron asking for a repayment schedule. Byron has now promised to start repaying in May, although I strongly suspect this is another excuse.

Byron’s wife has been very ill for the past year or so, and he claimed this is what he needed the money for. Some aspects of his story don’t add up, but nothing can be proven. We live in a country with subsidized public health care. Byron is over 50 and always seemed to be financially comfortable over the few years we have worked together. We are quite well-paid for teachers. I suspect Byron is in debt for reasons he is ashamed of and perhaps his wife doesn’t even know, although I have no proof. In any case, Byron was dishonest when he claimed he would pay the money back next payday. I have two concerns. First, that Byron may ask other teachers for a loan, as no one else knows about this. Second, that Byron is in serious financial trouble and in denial to himself and everyone—loan shark, gambling, or something like that. My options are to keep quiet and let Alex deal with it, quietly warn other teachers I consider vulnerable not to lend money to anyone, or see if Byron is willing to talk about it. I suspect Byron would tell me the same suspicious story he told Alex. Any advice?
—Concerned High School Teacher

Your best bet is to encourage Alex to look into his legal options for recovering his money—although he should probably assume that it’s gone for good and may decide it’s not worth spending any extra time or money in small claims court (or its equivalent in your country). Whatever he decides to do, you don’t have standing to take Byron aside and say, “Hey, you really need to pay Alex back. By the way, have you been lying about your wife being sick? Because you always seemed well-off to me.” There’s no incentive for him to tell you the truth, assuming that he is lying. There’s always the possibility that he really doesn’t have the money. I have sympathy for Alex, but he offered a colleague a substantial personal loan without signing anything or determining a repayment schedule beforehand, and I think he ought to have seen some of this coming. Regardless, you can’t fix this situation for him. I do think you have grounds to warn some of your colleagues against extending Byron another loan if he approaches them, especially if they’re tenderhearted and not especially well-fixed themselves. Double-check with Alex first to make sure he’s comfortable with your mentioning it, but if Byron was willing to do it to one co-worker, he’s likely willing to do it to another.

Dear Prudence,
I am a woman in my late 30s marrying the woman of my dreams this fall. I will not be inviting my mother and, by extension, my father. Everyone seems to assume this is because they are opposed to gay marriage, but that’s not true. They support gay marriage, and in fact we pretty much agree politically on all points. They just don’t like me as a person—which is sad, but also I don’t really like them either. So how do I navigate this? I don’t want people maligning them as bigots, because they are not. They are just regular, run-of-the-mill assholes I don’t want anywhere near my wedding. I don’t like them, and though I will admit I do feel some sort of suppressed glee when people assume they are horrible (immature yes, but I am human), I don’t want them thinking they are horrible for the wrong reasons.
—Estranged for Other Reasons

I would encourage you not to worry about your parents’ reputation among people they will never meet. You’re responsible for not telling lies about them, but you’re not responsible for their reputation in general. If people ask you directly, “Are your parents not coming to the wedding because they’re homophobic?” you can correct them and say, “No, we’re estranged for other reasons,” but you don’t have to call up everyone who might assume your parents aren’t coming to your wedding because you’re marrying a woman and say, “Just so we’re clear, they’re nonhomophobic jerks.”

Classic Prudie

“My future mother-in-law would like to wear her wedding dress to our wedding. I’m less concerned about the dress and more concerned about what this says about our future relationship. She is a very kind, considerate person, and I am certain that she knows this is not a very nice thing to do. What could her possible motivations be, and what should I do about it? I’m inclined to let her wear whatever she wants, as it doesn’t bother me as much as maybe something else would. Should I pick my battles, as they say? Or will not saying something make me seem like a pushover?