I’m Seeing a Much Younger Man. It’s Incredible—But I’m Worried Something Isn’t Right.

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 am recently divorced with a high sex drive. While I am not ready to dive into the dating scene just yet, I have met someone who, after many conversations, appears to be a good potential friend with benefits situation. Because we have some fundamental incompatibilities long-term (it’s related to kids—I’m done, he wants at least one), I wouldn’t consider him a serious romantic partner.

We have already had mind-blowing sex, and I would like to continue this setup, but I have some ethical concerns. I’m worried he is at risk of getting complacent with our setup (we really get along well, make each other laugh, and have a wonderful time when we get together for non-sexual activities), and he will miss out on his ability to meet someone who he can have a meaningful relationship with that wants kids.

It’s only been a few months, so maybe things will fizzle, and he’ll spend more time looking for someone who is a better long-term fit soon. On the other hand, when I’m not with my kids, we see each other multiple times a week and text multiple times a day. I’m nearly a decade older, and I’m worried that if I keep the status quo, he’ll miss out on something important to him. We’ve had multiple conversations about this, and he does not think our friends with benefits status will impact his fatherhood goals. I’d really appreciate an outside perspective.

—Maybe Unethical But So, So Good

If both of you are willing to enjoy the sex, texting, and generally wonderful times now, at the cost of potential loss and mourning of the connection later, that is a choice you each get to make. Depending on where he’s at in life and what he feels ready to pursue, he may not be interested in looking for a person to have and raise children with yet. Your ability to be at peace in this arrangement is going to hinge on whether you can believe what he tells you.

Is your friend with benefits old enough to rent a car? Is he of consistently sound enough mind and judgment? And generally someone who you can trust to assess the choices he’s making and accurately communicate his boundaries and desires? If the answer to all three is “yes,” worry less about his decisions for himself and more about the effects this relationship might have on you. If the answer to one or more is no, consider whether it’s a good idea to have a sexual relationship with him at all, and also worry about the effects this relationship might have on you, too.

No matter our intentions or our knowledge that a relationship has no long-term future, the combination of enjoyable sex (or, really, any sustained physical contact like snuggling), consistent and copious communication, and shared rapport has a way of fostering a connection and attachment to someone. The status quo becomes the routine, which becomes something one or more of you are likely to miss when you exit each other’s lives. Yes, on very rare occasions, friends with benefits arrangements do turn into lasting, no-sex-involved friendships when the time comes to end that part of the relationship. Even more rarely, both people find forever partners who are OK with or appreciative of the history of the connection. The vast majority of the time, though, the friendship falls apart when the shift away from sex happens, or future partners struggle to understand the situation or feel secure. One-off instances of sex that turned into friendships are one thing, but genuine friendships that had a big component of fantastic sex for several months tend to send people spinning unless you’re in experienced polyamory communities. So, how are you going to feel when your friend is less present in your life, or chooses his new romantic partner over continuing his friendship with you?

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Dear How to Do It,

My partner, who is a 50-year-old man, and I, a 49-year-old woman, consider ourselves open-minded and sexually adventurous. We enjoy exploring kink together and have pushed our boundaries in ways that feel consensual, connected, and exciting—things like dungeon parties and situations where the idea of being seen adds to the thrill.

Lately, we’ve found ourselves drawn to the idea of expanding our experiences further: a threesome, or possibly connecting with another couple. The fantasy itself is exciting to both of us. However, we’ve hit the same emotional roadblock from opposite sides.

I’m not sure I could realistically tolerate seeing him touch another woman, and he feels similarly about another man touching me. Intellectually, we like the idea of non-monogamous experiences; emotionally, jealousy and protectiveness seem to kick in the moment we imagine it becoming real. How do couples navigate the space between fantasy and reality when desire and emotional limits don’t quite align? Is this something that can or even should be worked through, or is it wiser to accept that some fantasies are better left unfulfilled?

There’s no time pressure, and there’s no requirement to progress your kinkiness to a certain level or particular destination. Essentially, think of it less as the two of you riding an escalator and more like you’re both floating through a three-dimensional cloud of possibilities. There’s space between where you are now and watching each other physically engage with outside partners.

I’d start by clarifying what turns each of you on to imagine or talk about without bringing up any of that jealousy. The two of you could enjoy that uncomplicated zone of eroticism for a very long time. Because it does sound like you both want to push those edges, though, get nuanced about them. Are there scenarios in between the potential ambient voyeurism of a dungeon or sex club and physical contact that feel interesting but manageable in the emotions department? One example of that would be explicitly arranging for other people to openly watch you. Another is being one half of two couples having sex in the same room, without touching the other pair. Or inviting a third to observe and masturbate, again, without touching. Are there types of touch that bring up less jealousy (or no jealousy) when you imagine them, but are still thrilling? Sometimes expanding what you’re imagining and fantasizing about is more than sufficient.

If you do decide to involve other people, be clear with them about your level of experience and the fact that this is new for you. Set a simple safe word, such as “red,” “bicycle,” or “stop,” and make sure everyone knows that they can use it at any time and it means, well, everything stops. Pay attention to each other during the interaction—facial expressions, body language, and other cues—and feel free to check in verbally if you aren’t sure whether everyone is OK.

The importance that you put on consent and connection will serve you very well. Following what’s exciting the two of you, without overwhelming you with difficult feelings, will help you focus on the point: pleasure.

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Dear How to Do It,

I just got something from my wife on Christmas that I eagerly look forward to: a blow job. She gives the best head I’ve ever had, but the problem is she’s stingy with it. The only times she’ll blow me are holidays, special occasions, and my birthday. How can I show her I would really appreciate it more often?

—Hoping for More Head

Dear Hoping for More,

I suspect there’s something other than the absence of enough appreciation that is preventing frequent fellatio. Has your wife said anything over the time you’ve known each other that might give you a clue as to what that is? Maybe she has temporomandibular joint disorder (also known as TMJ), has never found anything inherently appealing about giving oral sex, or feels like you’re pretty stingy yourself when it comes to doling out orgasms for her. Other possibilities that immediately come to mind are mishaps in your marital relationship outside of the bedroom or the possibility that she feels overwhelmed in the rest of her life.

If anything I’ve listed is ringing a bell, or other potential factors are coming to mind, you can try to address those (though TMJ usually requires some kind of medical intervention, which might include avoiding activities that keep her jaw open for extended periods of time). Remember that any actions you take to try to make your marriage more conducive to her giving you head are not guaranteed, and that totally transactional approaches tend to turn people off.

Most likely, though, this is an emotionally sensitive situation, and you’ll be best off proceeding with caution and delicacy. She’s your wife, after all. You (hopefully) don’t want to blow up your marriage over a blow job. If you’ve had successful conversations about sex in the past, use what’s been helpful previously to help you approach this. Do your best to aim for the goal of understanding why you aren’t receiving oral often, and of working through this discrepancy in desires as a team.

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