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Hey 19 (at heart)

Dear Sasha,

For the past year I’ve felt more and more confused about men.

I notice a pattern in my relationships with my past partners: essentially, I have sex with them because of my romantic feelings, with hopes that those feelings will be returned. Of course, I’ve heard “Why buy the cow when you can get the milk for free?”, but with my past two partners I couldn’t help myself.

I haven’t even had that many sexual partners, but I’m feeling more and more depressed about the relationships I have with men in general. I am way too young for marriage, although I would like to find a lifetime partner one day.

My real problem is that I feel men lose all respect for me after I have sex with them. I simply don’t know how to act afterwards. I worry that women are seen as clingy if they’re the ones to call first, so I never call, even though I want to. I’d rather appear strong than open and honest or emotionally weak.

The day after, everything falls apart. I’m traumatized that I’m left empty-handed. I hate myself for getting what I wanted. I get upset and promise myself never to have sex out-side a relationship again, which in turn leads to sexual encounters being few and far between. The last interval was almost one year. The time between partners is enough to make me forget the heartbreak I felt before, and thus the cycle continues.

I want to start dating again, but I don’t know how to go about it. I don’t want to seem promiscuous, but at the same time, being a tight-ass gets me nowhere either.

Sasha, although I’m young, I’m terribly afraid that I will live out the rest of my life alone or in pain because I can’t get away from this stupid habit.

Jaded

I don’t know what your biological age is, Jaded, but like so many of us, at heart you seem to be a thrashing teenager with a gaping wound for a soul. That’s why you see your entire life unfolding in front of you without logic or agency. That’s why you call yourself Jaded after what seem to be less than half a dozen sexual partners. That’s why you can be so sure that your entire life will only be one single way forever and that you must simply accept this.

It’s fine, I remember thinking, prone with self-pity on my matzo-thin futon after my HPV diagnosis at 19, I will just be celibate till I die. This thought filled me with that hallmark duet of youthful emotions: despair and superiority.

“I have a theory that sex was more complicated for me when I was in my early 20s because I was constantly struggling, on a broader scale, with questions of who I was, what I wanted and what I felt I was constantly giving up and giving in to,” says an author friend skilled in unscrambling the cruel, inflexible laws that govern adolescence.

“At the best of times, sex is incredibly liberating and fun. It aligns you with the other person or persons involved. It’s something you share for a minute, an hour or through an extended long-term relationship. It’s what you need and what you get. At the worst of times, sex is giving some-thing up, be it power or control, an act you regret because you feel you’ve given something up, which then makes you feel shitty on the long walk home.

“The key to this problem is to try and peel away the bullshit of hating yourself for wanting what you want and needing what you need and focus on finding a way to engage with people you want to have sex with and do have sex with that does not discount the possibility of having sex but keeps in mind your typi-cal feelings post-sex. There is a happy medium between being a tight-ass who never has sex and a promiscuous sex-regretter. Finding that middle ground means figuring out something about the person you are the next day.”

Here’s hoping you grow weary of the self-imposed hair shirt that forces you to spout fatalistic truisms about cows, virgins and whores, Jaded, and are able to look back on this stage of your life with the same incredulity as so many of us. Adolescence? Really, what for?

Dear Sasha,

A friend of mine is embarking on an impossible mission in my eyes. He’s trying to convince his girlfriend of five years to enter into an open relationship. His secret and only wea-pon is a simple statement: “A relationship should be monogamous, but sex should not.” I thought he was crazy and expected him to be joining me and my single buddies very soon. Then I thought, “Maybe he’s on to something. Maybe that’s the secret to keeping guys and gals from pulling a Tiger or Jesse.”

Could you shine some light on the matter, as it makes for interesting conversation?

Hunting for Answers

This is a wonderfully charitable and openhearted vision of non-monogamy, Hunting, but it discounts the fact that many people cheat not because their partner isn’t receptive to opening up but because they don’t want their partner indulging in the same pleasures they do. Yes, people step out because their partner is not on the same page sexually as them. But they also cheat because they’re selfish dick-swabs who don’t respect their partners’ needs and health.

I’m going to guess that if Tiger Woods found out his wife was banging a plethora of scandalously employed men without informing him, he would have backed over more than just a fire hydrant and a tree. I doubt very seriously that Jesse James would have left his marriage with the same grace and dignity Sandra Bullock showed if he’d found out she was getting it on the side.

Your buddy is onto something, it’s true. And if all goes according to plan, his girlfriend will be as well. He does know that, right? If his one and only argument is simplicity, I can assure him that he will not find it in this model. That line of thinking is akin to the theory that being a lesbian must be so much easier because women “know” each other.

Got a question? Ask Sasha: sasha@nowtoronto.com

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