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Slutscapades: 7 Tips For Having A Progressive, Sex-Positive Holiday Season

by Dr. Helen Shepard

Eight years ago, I made a New Year’s resolution: five or fewer men in 2010. I was 24 at the time, even hotter than I am now (which, I feel for transparency sake, I should say is still relatively hot, but way, way grumpier) and at a point in my life that was completely whimsical. The sluttiness of 2008 and 2009 had brought me sex on the beach with a man I’d just met, who became my abusive partner of eight months and the kind of heartache that only comes from falling in love while on drugs at a music festival or falling in love while three miles high on a Himalayan backpacking expedition; my heart flew permanently, obnoxiously outside of my body.

Not all the slutty experiences were bad. On a first date, I received cunnilingus while I played Guitar Hero. I once received cunnilingus for an hour, on the floor, next to a fire, in a three-sided snow shelter. I mastered the art of the sexual proposition, when I approached a guy in my shirt and panties after a night of drinking and said simply, "Hey, do you want to have sex?" The bad part of that story, is the guy was the on-again-off-again boyfriend of my only friend at the time. Sex had become so easy and trivial, that it seemed to be getting problematic.

So, I vowed to hook up and/or fall in love with five or fewer men that year. I didn’t casually fuck anybody’s boyfriend that year, and since condoms and showers are remarkable at keeping sexually transmitted infections at bay, that was never really my concern. But, fucking four men and one woman that year didn’t really keep the heartache away.

The first man of 2010 was a repeat from the year before—Festival Hottie. Was it the romance or the drugs that kept me hearing music, seeing fireworks and feeling like light was exploding out of my heart? When I hooked up with him again, we weren’t on anything (weed doesn’t count!) and I still felt a lot of the same feelings—unfortunately, that included the obsessive heartbreak when he didn’t want me. I sobbed in the car with my best-friend-slash-occasional-lover and my resolve strengthened.

I did a good job of keeping things casual with my next lover—the next that I remember, anyway. But, it’s unfortunate that a real, other person would get involved with me at a time that I had a resolution to be less emotionally involved. He loved me and I never truly loved him back—not even when he went down on me at the back of an Avett Bros. concert, fully visible to anybody who cared to look, though far enough away from other people that at least nobody said anything. Okay, maybe I loved him a little for that—he and I had several of my best-sex-ever moments—but, I never loved him the way he wanted me to.

In the midst of not loving my second partner, I met a third, who never minded that I didn’t love him. We met at a bar and fucked almost daily for a few weeks, then fell out of touch naturally. Casual sex success!

My fourth lover was my best friend, giving my second lover a happy-birthday-threeway. Years later, she would break my heart in the devastating way that best friends do—somebody you’ve shown your everything to and still had them love and accept you, only to suddenly stop caring about you because they found another lover. That kind of heartache. But, it wasn’t 2010, so for the purposes of this story, it’s all good.

The fifth and final lover I truly loved, and it did break my heart. It was a classic moment of, "I don’t want a relationship," "Great! Me neither...oh wait, yes I do, I want a relationship with YOU!" It happens so often, but it’s never fair. You get involved with somebody, telling them you want one thing and then hormones take over your rational mind and you find you don’t really know what you want anymore. After we broke up, I still had many months left of 2010 and didn’t know what to do. Should I break my resolution to cleanse my palette of the heartbreak or had enough been enough?

I technically succeeded at my 2010 resolution, but it didn’t decrease my dissatisfaction with romance or myself. I made a new resolution: plenty of men in 2011. I changed my overall sexual attitude, from one of hesitancy (like I was giving something up with every man I loved or fucked), to an attitude of abundance. I decided that I had so much energy stored up, that I could be free to give it to whomever, whenever I pleased. This wasn’t much different from the way I had lived previously, but with the key difference that in 2011, I would strive to have both fewer reservations and ultimately less heartache, due to fewer attachments. I’m happy to say, that this resolution also worked.

Although I didn’t have sex with many more men in 2011 than I did in 2010, my heart was never broken. Sex and love were no longer things to fear giving away—they were just things that came and went, like a tide.

If you’re sick of making and breaking the same cliché New Year’s resolutions, consider changing your philosophy on sex and love. It doesn’t have to be purely about numbers. Consider "embrace the peen in 2018!" or "explore the spaces in between in 2018." While it may be tempting to make a resolution of reservation, I found that the real growth came from attempting to keep nothing back. In the end, I found my reserves were actually greater when I treated them like they were endless than when I tried to conserve my open heart.