You’re cheatin’, heartless

Hello readers!
I am taking 14 days off my column for the first time in almost as many years. This means that for the next two weeks you will be reading Best of Love Bites, carefully selected by our dear interns. Enjoy

Dear Sasha

I have the ultimate opportunity that I don’t want to give up on but do need some help to achieve. My wife of three years is going on a business trip next week in Vegas, which will unfortunately leave me at home to pleasure myself. I am thinking that this might be the best chance I will ever get to have a casual encounter with someone new and exciting.

The problem is, I have never had a one-night stand before. I wonder what is the easiest and best way to approach women about the idea, and where is the best place in Toronto to quickly “hit it off” with girls looking for a night (maybe two) of pure fun and safe casual sex? Also, are there any surefire signs to look for in the conversation to get an idea of how great it is going?

—Any Lusty One-night Stands

Wow, my absolute favourite question—it must be Christmas! How can I get some easy, breezy vagina gratis while the little woman is out of town? I especially love that you ask me this as though, by virtue of this being a sexuality column, you are entitled to a courteous and reflective answer. Better still, you seem to imagine the only thing standing between you and some free sex is your wife and some inexperience. If only she’d just scram and you had the proper tools—some jazzy lines and good intuition—casual sex with multiple women would be all yours.

Cheating on one’s spouse while they’re out of town is not “the ultimate opportunity.” Many people, married or otherwise, might actually see it as an unmitigated abuse of this commitment, or at least something to give due consideration. But look at you, you’re putting on your Wayfarers and pulling out Bob Seger’s Stranger in Town with an attitude so upbeat it’s indecent. It blows my mind that queers had to beg and scrape and picket and sign one fucking petition after another to acquire the sullied privilege of marrying, but thoughtless, hypocritical pricks like yourself can just up and do it without an ounce of contention.

So then... onto the actual advice part (though yes, it will be scorching as well). Not surprisingly, there is a Web site for people just like you. Ashley Madison’s (www.ashleymadison.com) slogan is “when monogamy becomes monotony.” The Web site candidly caters to those seeking extramarital affairs so the only person you’ll actually be lying to is your wife. My guess is it might take time to scare something up though, since a lot of these ladies are the bubble bath and satin and roses and hot-air-balloon-ride types—big dreamers with dashed hopes and shit husbands, I guess.

The site creates an atmosphere of infidelity being totally routine (and yet fun and exciting!), pop-up quotes about people who seek out affairs being better-looking than average, that sort of thing. But to me, it’s more an unconscious critique of the very institution it opportunistically feeds off of. Going through people’s profiles, they talk about being unsatisfied, or not getting what they deserve, but isn’t posting romantic ambitions on a Web site rooted in deception just pandering to the same issues of denial and unreasonable expectation? The enthusiastic pragmatism of the site seems like such an absurd way of acknowledging the inadequacy of many peoples’ marriages, like those advertisements that try to rally enthusiasm around a product you didn’t even know you needed.

And just a note to the proprietors of Ashley Madison: posting articles about ethical polyamory on a philanderer’s site is like putting pictures of hands on a foot fetishist site. Just because it’s attached to someone, doesn’t make it the same thing.

Got any questions for Sasha? E-MAIL: POULEDELUXE@YAHOO.COM