Friend Without Benefits

Reader question: “I am an older woman who has always appeared to be “good.” I was married for over two decades and have a teenage daughter. My marriage was pretty much sexless, and we’ve been divorced for five years. I had a raging hot uncommitted relationship after that lasted four years — but went nowhere. I started dating a good friend two years ago. This man has treated me like a QUEEN! He is a touch jealous (which I can’t stand), but he is an amazing person. 

However, he is TERRIBLE in bed. After 20 years of a sex-free marriage, I learned that sex is a big deal for me. It’s a part of who I am. And having to endure “getting through it” with him is an issue for me. I have tried to teach him, but there’s so much to teach that I’ve grown frustrated.

I really want to have a couple of other men on the side. I can’t discuss this with anyone in my cohort because I’m not a big believer in monogamy — and they all are. Can I do this? Please? Or would you suggest something else before I take that route?”

Answer: What you describe is a dilemma many face: trying to find single human person who can meet all of our romantic and sexual needs. It’s a lot of pressure to put on an individual, and yet over the past few decades we have come to pile more and more expectations onto our partners.

In centuries past, marriage was largely an economic institution, serving to protect family assets of the wealthy and to create sustainable domestic units among the working class. For most of human history, love was not a prerequisite, though it *might* be fostered during a marriage, through working together to run a household and raise a family. To have sexual compatibility with a spouse? An outstanding surprise, a result of fortuitous pairing.

In modern marriages — particularly monogamous ones — we demand that our partner be a good domestic teammate while also our romantic and sexual match. We may also expect that person to be our best friend, someone who also meets our social, emotional and recreational needs. Add to that the pressure to bring in comparable amounts, financially.

Interestingly, this has made some people much happier. If we invest deeply in a relationship, the payout can be huge. For others, though, the expectations are so high that they feel disappointed, even when the situation is objectively good.

A dilemma many face: trying to find single human person who can meet all of our romantic and sexual needs.

Which brings us to your situation and proposed solution: having multiple partners to meet differing needs. You have a good friend and support, but you also have significant desires that are going unsatisfied and you feel are unlikely to be met by him. It would make a ton of sense to continue to engage in an intimate, companionate relationship with him while having your sexual needs met elsewhere.

The question is whether that would meet his needs as well. You describe him as jealous, but don’t mention if you’ve asked him directly about opening up things. That might be a first step: having an open, honest conversation about the things you both want, need and fear.

His penchant for jealousy doesn’t mean he couldn’t learn to navigate non-monogamy. He would just need to be motivated to work on it. Non-monogamous people feel jealousy as well, of course. Jealousy is simply our brain’s way of alerting us to some insecurity or unmet need. It can happen in any relationship, including non-sexual ones.

Before we ask this man to change his life to accommodate a new model of dating, there are questions to ask yourself. The first: why are you with him? Do you have romantic and sexual desire for this person? Or did you just fall into that kind of interaction? Research shows us that we tend to push forward in relationships even when it’s not working because we fear being alone.

Your message is filled with clues that you desire steamy, passionate fucking. It sounds like you not only have this innate craving, but also want to make up for lost time. And that’s cool. You have identified a need! You have also decided that you don’t want to have to labor over the process of training a lover, which is also cool. You have identified a limitation.

We must identify our needs, wants, fears and limitations so that we can clearly communicate them. This is a good place to start.

You mention that you had a steamy affair that lasted four whole years but say it “went nowhere.” I’m curious where you wanted it to go. Four years is longer than many significant relationships. Were you hoping to get remarried? Is that a desire or goal you have?  If so, what do you need from that person? Is it important to you that your conservative friends approve of your lifestyle? Does that factor into your decision to stay in a commitment that is so deeply unsatisfying?

If you draw your current partner in a mono-poly arrangement, it’ll require a great deal of work and skill building.

You ask if you can have multiple lovers. If you want my permission, you have it. But if you draw your current partner in a mono-poly arrangement, it’ll require a great deal of work and skill building on both your parts to sustain.

And if you don’t have the patience to teach this man how to fuck you right and his jealousy is already frustrating to you, I’m gonna guess you’re not gonna be stoked to go over the nuances of consensual non-monogamy with him either. That sounds like a really efficient way to turn a friend (without benefits) into an ex to whom you don’t speak.

My suggestions are to do some more thinking about all these things and if, in lieu of other men on the side, you might just want other men entirely — to start over fresh with the plan to date as a solo poly person. Also, if you can’t safely talk to your friends about this, you might also want to start a hunt for new friends too. You can have several of them as well. Good luck!

Have a question for Dr. Timaree? Send an email to asktimaree@philadelphiaweekly.com.

    • Timaree Schmit Headshot

      Timaree Schmit is basically an episode of Adam Ruins Everything, but in the shape of a person. She has a PhD in Human Sexuality Education and years of experience in community organizing, performance art, and finding the extra weird pockets of Philly.

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