Help! I Want to Ask Out a Woman More Than 20 Years My Junior. Am I a Creep?

Dear Prudence is Slate’s advice column. Submit questions here. (It’s anonymous!)

Dear Prudence,

So, say you were in the middle of a long dry spell. You’ve dated, but none of the men really interested you. Then, there is this guy that is several years older than you who is unattached. At work, neither of you report to the other, but you see each other, and are members of the same non-work groups—book club, gym, game-night groups, that kinda thing. He’s almost your dad’s age, you’re a few years older than his oldest kid. He’s been divorced for a few years, you’ve never really been attached or engaged. If he asked you out, would you freak out? Would you end the friendship? You’ve been out together many times for drinks or dinner, both alone and with friends, he’s very current culturally, and very passionate about things that you care about. I’m the guy in this scenario, you’re the younger woman. The woman in question is 43, I’m 69.

–(Not) a Cradle Robber

Dear Not a Robber,

My word! I’m all a-flutter to have been cast in this exciting romantic scenario. And in the role of the ingenue! Well, let me get into character. I’m 43 … bad dates … I go the to the gym … OK, got it.

If what you’re truly looking for here is an official judgment on whether your age gap is acceptable, sure, I’m happy to make that. In fact, I am the world’s leading expert on whether age gaps are acceptable. A 69-year-old guy and a 43-year-old woman would be dispiriting, but just barely acceptable. Congrats to you.

Should you approach her? Who knows! Maybe she likes you. I’m inclined to think that if she were romantically interested, she might have expressed something during the drinks and dinners you’ve already shared which were not, apparently, dates. I’m also inclined to think that if your social life already includes drinks and dinners with this woman, alone and in groups, you might be better served to simply continue ambling along this path for a while, waiting to see how things develop naturally, rather than impatiently forcing things down Romance Road. On the other hand, you’re 69! Maybe you’re just eager to make something happen before you retire.

As to her potential reaction: Most single women I know in their forties would not freak out if they were asked out by someone two decades older than them. Indeed, the dating ecosystem being what it is, most of them are already asked out, almost exclusively, by men two decades older than them. My guess is that if you ask your coworker to go on a date, she’ll be grimly unsurprised by this development. She may already be dreading it.

–Prudie, resignedly

Got a question about kids, parenting, or family life? Submit it to Care and Feeding!

Dear Prudence,

My mother dragged me through her multiple relationships since my father died when I was a child. Including uprooting me twice to move to a different state because her boyfriend was there. It left me with a lot of insecurity about intimacy and trust. I am always waiting for the other shoe to drop. Now I’m an adult, and my mother is engaged. Again. But this time the man seems decent.

My problem is that my mother is demanding that I use my limited vacation to spend a week at his family compound this summer. Apparently, all his children, siblings, their children, and all the grandchildren go every summer and enjoy the great outdoors. I am not outdoorsy at all. And I really don’t want to send my limited vacation and funds to attend a stranger’s family reunion. They might be lovely people, but frankly I don’t care. This is the same pattern my mother has indulged since my father died and I am tired.

Any time I bring up my feelings, my mother accuses me of being negative and pessimistic. She says I just don’t want her to be happy. I am happy that my mother is happy. I am not happy about the demands to get on a plane, rent a car, and drive hours to the middle of nowhere to socialize with strangers while bugs eat me alive. How do I talk to her about her expectations here? Or should I just lie and claim to have to work?

—No to the Family Reunion

Dear Family Reunion,

You have already clearly delineated the two options here, given that you are clearly not interested in spending a week at the Kennedy compound in Hyannis Port. (Congrats to your mom on landing a scion!) I wouldn’t blame you at all for taking the easy way out and simply claiming work obligations. “Oh, I so wish I could be there,” you could say to your mom on FaceTime, as Kennedy cousins frolic on waterskis behind her. “But these protons won’t smash themselves!” After all, it can be exhausting simply imagining the difficult conversations we must have with our relatives, steeling our courage to explain the lifetime’s worth of damage and disappointment that we feel.

But remember that if you do choose to initiate a conversation about expectations with your mother, it is not necessary for that conversation to cover all the terrain that it might cover in your head. That is to say, your peripatetic childhood and the insecurities it caused are fit subjects for your therapist, but bringing them up to your mom is not going to do anyone any good in the year 2024. She can’t change the past; nor can you—and anyways, she’s just going to view criticism of her past behavior as an indictment of her current Kennedy and get defensive.

So restrict your boundary-setting discussion, should you have one, to the present. “Mom, that’s a kind offer, but I’m afraid I don’t have the money or vacation time to fly to Cape Cod this year. Please don’t pressure me, as it simply makes me feel bad. But I’m really excited to meet Reginald, who seems [use the adjective of your choice here, but probably you’ll want to improve on ‘decent’], and I’d love to invite you to come out for MLK weekend/Easter/Memorial Day.” Be persistent and follow up on that invitation; let your generosity guide the conversation forward.

–Prudie, munificently

Dear Prudence,

For reasons I’ve never quite understood, my husband and my father seem to hate being around each other. They’re both incredibly polite, they engage in formulaic small talk, but the interactions are awkward, stilted, and uncomfortable. Individually, they’re the life of any party. Together, they suck all the oxygen out of the room. My parents are getting really old, so we’re spending more time with them and neither of them are happy about that. How do I navigate this? Ask my husband to stay away? Ask them to go to therapy together? Sit them down and tell them I expect more from them? They seem to be doing their best to get along but are both clearly gritting their teeth while doing so.

–Oil and Water

Dear Oil,

You’re saying that your husband and your father, despite not really liking each other, are totally civil, never get in arguments, and limit their interactions to the minimum necessary niceties? My dear, you are a lucky person. The two most common modes of interaction between fathers-in-law and sons-in-law are a) bitter, loud fights about politics and b) endless, boring conversations about football. You’ve escaped both! Pat yourself on the back.

It is of course a shame that these two vibrant men you love can’t seem to click. If the two men share any favorite activities in common, feel free to organize a golf outing or whatever, but be prepared for them each to feel that the presence of the other has cast a pall even on the golden-hour beauty of Pebble Beach. And if your father truly is “really old,” I’d ask: What is the value of pushing it? These poor guys are doing their best. Trying to rebuild their entire relationship from scratch is neither your responsibility nor a task likely to yield anything other than frustration.

–Prudie, laboriously

Dear Prudence,

My wife and I are in our late 40s. Our two children are in middle school. My mom is elderly and divorced, and her health is declining. I think it would be best for her to move in with our family. That will be a much easier sell with my mother than hiring a stranger to help her or moving into an assisted living facility, and both those options are very expensive.

When I brought the topic up with my wife, she said absolutely not. I was surprised, because my mom and wife have always gotten along great. She told me she loves my mom but she’s not up for it. How can I convince my wife that I should take on my fair share of the caregiving for my mother?

–I’ll Do My Part

Dear Your Part,

You cannot convince her. I don’t recommend you try! For the decision to bring your mother into your shared home is not a decision that is simply about you “doing your fair share.” It would be a decision with dramatic impact on everyone in your family—most particularly your wife, who if she is like most American wives already does more than her fair share of the caregiving and domestic work in your house. She has every right to object to the notion of bringing another person into the home, especially one whose daily needs, unlike those of your children, are only going to increase as time goes on.

Do some families bring an elderly relative to live with them and find joy, togetherness, and intergenerational familial wisdom in the process? Yes. But your wife doesn’t see that happening, and you would be well-served to treat her “absolutely not” as definitive at this time. If you argue with her further, you’ll only harden her resolve; if you, somehow, force the issue, you’re setting yourself up for decades of resentment. Perhaps financial circumstances will one day force your hand. Perhaps, over time, her feelings will change. But you will not be the one to change them.

–Prudie, equitably

Catch up on this week’s Prudie.

We (me, my husband, and our son and daughter) moved into our house about a year ago. We met the neighbors next door about two weeks in. They’re an older couple with grown kids. Our only interactions since then have been a friendly wave here and there. I mostly only see the husband outside, since he smokes. A few days ago, he was outside smoking when I’d just gotten home with my sister and daughter (she’s 2). I asked how his wife was, and he asked after my husband. We were about 60 feet apart so we were kind of speaking loudly. Anyways, he said something about how cloudy it was, and I responded with “Yeah, that’s why we left the park early.” Suddenly I see his free hand wander down to his crotch.