Very hot women keep telling me I’m a “DILF.” My wife is holding me back.

How to Do It is Slate’s sex advice column. Have a question? Send it to Stoya and Rich here. It’s anonymous!

Dear How to Do It,

I’m a 66-year-old married man, and we’ve been together for 30-plus years. I’m told I look like I’m in my mid-50s. I take good care of myself and stay as fit as I can. I have the normal aches, pains, and scars associated with living a full 66 years. I’ve always loved and respected women, and throughout my life, I’ve been told I’m attractive and attentive as a partner. Over the last several years, I’ve been told by very attractive women that I’m a DILF and a hottie, among other things. I have a very strong sex drive. The problem is that I haven’t had sex in more than three years. And I’m going nuts.

My wife has let herself go and just doesn’t seem interested anymore. We are both very open-minded people, and were quite sexually adventurous together in our earlier years. It’s a classic story, right? I’ve tried therapy (she won’t go, I do). I’d rather not get into the ins and outs of our relationship … it’s complicated, and I’ve practically made up my mind. I truly believe it’s not only important to be happy, but you also have to try to have FUN in life. I’ve basically decided to go for it. Yes, I’m talking about finding someone on the side.

Recently, I’ve found myself in a confusing situation. At a business establishment I frequent, a much younger woman—likely in her late 20s—seems openly flirtatious: strong eye contact, lingering smiles, personal questions. I’m very attracted to this woman and find it hard to extend eye contact with her. I’m embarrassed by the age difference and aware that I’m married, but the attraction feels mutual and real. Is it possible that a confident, attractive young woman could be genuinely interested in an older married man (not rich) purely for low-maintenance companionship, sexual connection, and fun? And if so, how should someone in my position even think about navigating that? People are always around us, so a discreet, leading conversation is not possible. The business is a high-end cannabis dispensary, so the environment is already slightly “charged.” The last thing I want is to come off like an old creep (I’m truly not!). I think whatever happens, if anything at all, I should play it cool and let her make the first move. Any suggestions?

—Forgotten How It Feels

Dear Forgotten How It Feels,

You know how they say that you shouldn’t go grocery shopping on an empty stomach because your hunger will drive you to overspend? Those are the vibes in your letter. You’ve got sex munchies in the weed store.

I agree that balancing happy and fun is important (it’s quite an easy balance, actually, as having fun will make you happy), but you know what else is important? Honesty. Loyalty. Honoring your agreement with your wife. Or are those things not important to you? I know I sound like a buzz kill. You don’t even want to go there in your letter (your swerve around your relationship issues is pronounced), but I think it would be useful.

You aren’t even trying to do this ethically, it seems. Maybe you have your reasons for this. Perhaps past conversations with your wife have made clear that an open relationship simply will not fly. Breaking up is extremely difficult, of course, and I understand the impulse to maintain the relationship while getting yours, but I am not convinced that you’ve done everything you can at this point to attain an ethical, sexually active lifestyle. Your wife just doesn’t seem interested anymore, but what does she say about the state of your sex life? Have you ever tried confirming your suspicions, or are you conveniently resting on them because you’re actually not particularly interested in your wife sexually? You mentioned that she “let herself go,” but that’s not a good reason to cheat on her either. Simply put, you need to talk.

Infidelity is not certain death for a relationship—it may even seem necessary at times to preserve your primary partnership—but I’m not loving the premeditated nature of your straying. Yes, it is possible that the weed girl is legitimately attracted to you (after all, you begin your letter by informing us that hot women think you’re hot), and that all that would be required to spark something is an expression of your interest. But should you do this? I don’t think so. Not without discussing your feelings with your wife, at least, and your desire to have sex with other people. There is a chance that she will agree to letting you go have your fun, and then you would have accomplished what you wanted without having betrayed her. It’s worth it to take the route that feels good all-around and does right by both of you. Try it. Given how long your marriage has been, it’s likely your wife doesn’t want to lose it either, and that may inspire her to work with you on finding a mutually OK path forward.

Dear How to Do It,

My wife is trying to persuade me to give her a rim job. I think this is disgusting, unsanitary, and a sure way to end up sick with E. coli.  When I voiced my concerns, she said I was being “difficult.” How can I get through to her that this isn’t a safe practice?

—Rim Repulsion

Dear Rim Repulsion,

Eating ass is not a sure way to end up sick with E. coli. I couldn’t even estimate the number of asses my tongue has been in over the past 25-plus years, and I’ve never had it once. Nor have I ever, to my knowledge, come down with any of the other bugs (bacterial infections like shigella and parasites like Giardia, alike), that are rimming risks. Rimming/anal play indeed has its unique risks beyond STI risks (which can be mitigated with barriers) because of the rectum’s specific functions and flora, but even monogamous partnered sex comes with the risk of UTI or yeast infection. It’s all somewhat risky. “Safe” is an illusion. A well-cleaned hole helps mitigate the particular risks in question.

That said, if you aren’t into rimming, you don’t have to do it. The language in your letter is judgmental, which may read as combative, or, yes, difficult to an interested partner. But your wife shouldn’t be pressuring you into doing anything you don’t want to do. I would shift your goal from trying to convince your wife that rimming isn’t safe to simply telling her that you are not interested in engaging in this practice and that the rules of consent give you the absolute right to turn her down. Keep saying no until she gets it.

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Dear How to Do It, 

I am a 29-year-old man, and I will be 30 in May. I was diagnosed with ADHD and depression when I was 17 and got medical treatment for it. I’ve been in therapy since I was 24, and there’s been notable progress in all areas of my life, except romance. I feel that I missed out on dating throughout my 20s, and I hate that I did because it feels like it’s the one period where people are relaxed about dating and exploration. Plus, people in their 20s have more time on their hands, and of course, they look better. Despite trying and showing up as my authentic self, it did not play out for me.

Now seeing many of the folks in their 30s, most of their conversations about finances, children, and marriage scare me. Many people were able to date in their 20s without having to bring these subjects up early in the dating process. It somehow makes me turn away from dating altogether because, unlike most people, I will always have a lingering resentment about how transactional it all feels, having missed out on a stage where most can connect and build a relationship organically rather than placing people in status and financial hierarchies. I feel lost, sad, and very resentful about not getting the chance to be an imperfect person. How do I get past this?

—A Bag of Missed Opportunities

Dear A Bag of Missed Opportunities,

Get out there and date. Your perceptions of the dating scene are based in reality, sure, but there are plenty of people in their 30s who don’t want children and don’t find discussing finances particularly interesting. In my opinion, marriage should not enter the conversation during the first few months of dating for anyone, though in many ways it’s better for everyone if people are upfront with their expectations. It makes it easier for all parties to filter out those who aren’t good matches. Rejection sucks, sure, but what arguably sucks more is being strung along or investing in something for an extended period that doesn’t end up panning out.

You have a very narrow view of what dating is, in part because you haven’t actually done it. Do not ignore your own power. When someone talks about things you’re not interested in on a date, that’s a good indication they aren’t a match. Then you move on and go out with someone else, hoping that their interests/visions for the future will align with yours. Or you attempt to cut out even the possibility of these discussions by saying in your app profiles, “I’m not interested in marriage, children, or discussing finances” (or whatever version of that sentiment works for you), and see what takers you get after that caveat. The game is one of trial and error.

You get to be an imperfect person in your 30s. Last I checked, there are imperfect people at every age, and they, in fact, make up the whole of humanity. I know what you mean in your letter about a certain frivolity that marks one’s 20s, but as a gay man in his 40s who still goes to clubs, likes weed, and plays video games, let me assure you that you can be frivolous at any age. Thirty doesn’t mean what it used to, and it’d be great for you to let go of what age is “supposed to” mean and instead embrace what it actually looks like. Speaking of that, people are hot well after their 20s. Men have it way easier than women when it comes to societal standards for aging—crow’s feet are considered by many to be handsome. Bette Davis said that men are best looking at age 45, and she died in 1989. Back then, 45 looked more like today’s 55. You’re fine, and so will be many of your potential mates. If you’re really so concerned with 20s culture, you could always date people a few years your junior, by the way.

So much of your letter just reads like excuses not to date. Aren’t you over that? You’re so bummed that you missed your 20s. Don’t talk yourself out of missing your 30s, too. The ticking clock should be as good a motivation as any. You have a life to live. Go do it.

—Rich

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