Dear Prudence

Help! A 28-Year-Old Man Wants to Date Me. I’m 56.

In We’re Prudence, Prudence asks readers for their thoughts on a question that has her stumped. The answer is available only for Slate Plus members.

A younger man hugging an older woman from behind, holding her hand.
Photo illustration by Slate. Photo by ajr_images/iStock/Getty Images Plus.

Every Thursday on Twitter @jdesmondharris, Dear Prudence asks readers for their thoughts on a question that has her stumped. She’ll post her final thoughts on the matter on Fridays. Here’s this week’s dilemma and answer:

Dear Prudence,

I am a 56-year-old woman who is single. I have a younger man who is interested in dating me. He has stated that he is very serious about his feelings. He is a true gentleman and is in business for himself (so I am quite confident he is not after money). Many people think I am a lot younger than I am, and peers who have observed the situation often encourage me to go out with him.

Here is the kicker: He is 28. I haven’t even allowed myself to truly consider going out with him until now. I don’t want to be considered a cougar or a cradle-robber. Heck, I think I am older than his mom! We do share a lot of common ground on various subjects, and if it weren’t for the age difference, I would have dated him in a heartbeat. He is aware of my hesitancy and has been working at winning me over for the past three months. I feel if we end up having a long-term relationship, he will miss out on a lot (having children being the main thing) and will be my caregiver as I age. He says that neither of those are a concern for him. Am I sick for even considering this?

—Age Anxiety

Dear Age Anxiety,

You are not sick for considering this. In fact, my first reaction was that is totally a nonissue and you should go for it. The only thing that gave me pause was that I asked myself, “What if the genders were flipped? Would I think this was creepy?” I honestly wasn’t sure, so I asked on Twitter.

The consensus there was that at 28, your suitor is a grown man and the age difference isn’t at all disturbing. Most people felt sure that his age was not reason enough not to date him, especially because you’re not in a position of power over him and he’s financially stable—so even if the genders were flipped, it would be fine.

28 is pretty solidly in adulthood. I don’t see any problem with this (and I still wouldn’t if the genders were reversed); big age gaps matter a lot less when both are fully independent adults. Two adults are interested in each other: go for it! —@Jen_Jaw

But I did agree with those who pointed out that the real issue here isn’t whether the age difference is objectively weird, it’s if you think it is, or you worry that other people will think it is (and to be fair, they might!).

Don’t do it, not because of the age difference but because she is over-thinking it and has anxiety over concerns/issues that are out of their control so I feel like all of that will end up being the cause of why they eventually don’t work —@Black_Ted_Mosby

She needs to decide if being the subject of judgmental gossip is a deal-breaker for her. This could end up being a fabulous experience for both of them, but only if they both have the confidence to pull it off. It sounds like he does, but does she? —@shannonhasQs

Can you get over those feelings? Only you can answer that, and you should have an honest talk with yourself about it.

If you decide you can be at peace with the age gap, my only other concern, inspired by some of the responses, is that you’re already thinking long term. A date is not a lifelong commitment, and you shouldn’t go into this expecting that it will lead to a lifelong partnership that involves caregiving and a child-free life for him. Contemplating all of this is not only too stressful, it will put undue pressure on a period of time during which you should just be getting to know each other. So make your decision based on dating, not on making him your life partner.

I mean… he could be with her to the end of her life and *still* turn around and have kids in a new relationship. He’d be an old dad, but those aren’t that uncommon. Her long term fears don’t really hold up under scrutiny, and I have a feeling she’s more stressed by the optics —@e_elenaaaa

Tell her to have fun & if it gets to it, they should draft a pre-nup that includes things beyond just money. But most of all: have fun! Go on a date & see where it goes. He is grown & knows what he is doing. All she should focus on is whether he makes her happy. —@TIAReports

You haven’t even had 1 date & you’re already thinking about the nursing home. The best way to figure out if you’ll be compatible for a relationship is to… go on a date! Maybe you don’t get married but you get to have a sexy short term fling that you can treasure in your old age —@rosalarian

Life is short, why not go for it? I’d enjoy it for now and if it gets past a certain point, then talk about the implications of a longer-term relationship —@imfeelingsocial

Why forego a relationship to avoid hypothetical situations? They don’t have to plan for forever to enjoy dating each other now. Live in the moment, baby! —@chuloconqueso

So, bottom line: If you’re interested, you should go on a few dates to explore your feelings. But do it without the expectation that this will lead to a long-term relationship—take the pressure off! And give yourself the flexibility to back out if you can’t shake the discomfort about the age difference and the way it’s perceived, whether or not it makes sense.

Classic Prudie

I’ve had two specific fantasies since puberty. Now, many years later, I feel my sexuality drying up and blowing away, and I want to check off these two boxes first. Except I am married to a wonderful person, whom I adore! I’ve asked, but she is not interested in these things. I’m not after anything dark or obscure. I could solve this problem for a few hundred dollars while on a business trip and that would be that. I never have, though, as my wife would be crushed if she found out. Is this kind of thing ever OK? How do other people handle this?