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25.09.2018

What happened when I scheduled sex with my friend-with-benefits.

Joe* re-entered my life at a time where I was having casual sex that was both mind-numbingly boring, physically unsatisfying and with people I wasn’t that into. It was the kind of casual sex you have for the sake of exercising your right to have casual sex. Which is to say, sub-par. Joe and I...
Time: 13:06     Date: 12.07.2018
US Living News: What happened when I scheduled sex with my friend-with-benefits. NY Post 24 - US News

Joe and I had history. We’d unsuccessfully dated 15 months prior (it ended with him telling me he “wouldn’t be that devastated if we stopped talking or hanging out”). Then later, unsuccessfully sexted for six months (it ended with him ignoring my requests to actually address what we had been doing and what it meant).

When I first met Joe years before at college, I developed a severe crush that I struggled to shake. Because Joe is the kind of person everyone conceptualizes as ideal. He’s progressive, so not a jerk, very intelligent, so can keep a conversation about any political or philosophical issue that takes your fancy, and endlessly charming. But above all, Joe is pragmatic.

Which maybe helps to explain how we came to a place of having scheduled sex. We’d had the dating and then the break-up and then the sexting which brings us up to the point where it seemed like a good idea for us to start hooking up again.

Putting it in the diary iStockphoto

You might say our crazy plan was doomed from the start, to which I say you are totally correct.

To be fair, in the beginning, having scheduled sex with Joe seemed like the logical solution to my casual sex woes. Here was a regular hookup with someone who I knew would prioritize my pleasure without the hassle of dealing with the crap that can come with the casual sex scene. It was also incredibly time efficient and left me free to pursue other people I was interested in. The whole situation was utopian – I was a sex genius! Save for the fact that I was lying to myself about the fact that I probably loved Joe and he would never love me back!

Deep down, I knew it was never going to work. But there’s nothing quite like the validation from people who have a history of rejecting you to force you into making questionable life decisions. Of course, they don’t seem like terrible life decisions until you’re five months deep, having regular, scheduled sex and crying the kind of tears that would give Kim Kardashian a run for her money after you send him a sext and he replies, “good to know.”

The plan iStockphoto

Inevitable heartbreak aside, this is how we organized things: We would message each other at the beginning of each week to see what our schedules were like, and then pencil in a time that would suit us both to have sex. As part of the agreement, we would prioritize seeing other people, not hook up with each other outside our designated scheduled slot and agreed to keep it only between us. Finally, we decided sleepovers were allowed.

Three weeks into this erotic experiment and after being the person who always had to organize the sex, I decided to silently strike – if he wanted to have sex, he could organize it. When Wednesday night came around and he still hadn’t messaged, I got irritated. I sent a message asking if he wanted to sleep together that week. He replied, yes, and that we should “coordinate at some point.” He ignored my follow-up. After more silence, on Thursday night I asked, “what’s the go?” I got a reply two hours later telling me that he was completely booked up that week, sorry.

This was frustrating considering he’s a master’s student, who has more time on his hands than an aging retiree. I expressed my annoyance, he apologized, we shifted gears and agreed on a set day going forward – Wednesday – to eliminate the need to coordinate each week. I put it in the iCal and we forged on ahead.

Unfortunately, poor communication skills weren’t the only issue with this arrangement.

Seeing other people iStockphoto

If you agree, as Joe and I did, that we should put seeing other people besides each other first, you will need to accept the difficulty when both of you hear about the other person dating new people. You will need to feel comfortable talking about their sex life outside the sex you are having them. And you will need to be strong enough to field questions from your friends, like, “if he’s dating someone else, does this mean he’s ready for a relationship?” or “how do you do this, isn’t it hard?”

Because it is hard. Being able to understand on an intellectual level that we’re able to love more than one person at one time doesn’t automatically exclude you from feelings of jealousy and insecurity. In these instances, it’s important to be kind with yourself.

Don’t get me wrong, having scheduled sex with someone who cares about sex being mutually pleasurable has its benefits; you can try things you’ve always wanted to safely, and the sex is better than ever because it’s with someone you’re comfortable expressing what you do and don’t like to.

But just as you shouldn’t settle for subpar sex with strangers for a short-term ego boost, you also shouldn’t settle for good sex with people who don’t care about you as much as you care about them.

There are two potential reasons as to why I lied to myself for so long about how I felt; 1. It was too painful to admit the truth of this person never feeling the same way as me, or 2. It was too painful to admit I had become the biggest cliche in the book, having scheduled sex – “friends with benefits” – with someone, secretly hoping it would work out but knowing it never would.

I don’t believe all iterations of consensual non-monogamy are doomed. I believe scheduled sex can work for people where unrequited love isn’t a factor and where effective, honest communication is.

Eventually, I stopped having scheduled sex with Joe after confronting the reality that there are better things I can be doing on my Wednesday nights than having masochistic sex with someone who just isn’t that into me.

*Names changed to maintain anonymity

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