I like a good chase. No, scratch that; I like a great chase. One that is flirty, clever, constant and often results in a few hours of debaucherous fun.

My problem of late is that I haven’t met many men that are skilled in the art of a good chase. I’m not sure what’s happened over the last 15 years, but –here it comes– back in my day, men (as I dated primarily men in my youth), knew how to flirt, tease, and be cleverly playful. I married one of those artistes, and there has been no substitute since those early days. We didn’t have texting or even email back then (holy fuck I’m old), so the art involved way more imagination and skill. Notes and packages left on my doorstep, answering machine messages, mailed letters, mixtapes, even flowers (do people even send flowers any more?). The fact that flirting has so many more lines of communication these days yet people fail to properly utilize them for flirtatious good is a sad testament to lust and technology. People have become just plain lazy.

In a world where messages can be sent and answered in milliseconds, we’ve become used to instant gratification. We refuse to put any real thought into our missives. When we’re asked to posit a message in less than 140 characters, out goes the art of communication, to be replaced by no-frills facts. I’d still rather wait for a well-written letter sent via post than a poorly constructed instant message.

But such is the century that uses pixels instead of paper, so I’ll take what I can get as long as it’s finely crafted. When I first started heavy texting, it was in response to a man who knew how to use words to his benefit (and mine). Our flirts were playful, witty, and got the job done with flare and finesse. We did it so often, we had to upgrade phones and service plans just to be able to keep up. But as all good things, that eventually ended, and other than my NumberOneMan, who himself is a master at wordplay, I have not been able to find a suitable replacement. Oh, I’ve had dalliances that included a few exchanged digital missives, but none enough that have satiated the lust in my brain as much as the lust between my legs. I’m sapiosexual as much as I am anysexual.

I’m not one to beat around the bush; if I’m interested in you sexually, you’ll know it. Life’s just too short. I do, however, expect/hope for the same honesty in return. What’s important here is the distinction between playful flirting and headgames. The art of the chase is something completely different from being an asshole. It also means that despite drawing something out in a skillful manner, you can still make your motives known early on. If you don’t know the difference, that’s a problem.

I once had an extended fling with a man whose company I quite enjoyed and when together, we had tons of fun, both in and out of bed. What I realized over time was that I was always the instigator of said fun; that I was the one always sending out the flirty invitations. I got tired of being the only one pushing the teeter-totter off the ground and I left the playground.

Luckily, new games were afoot with a clever artist who knew how to play, on and offline. That game was short and deliciously sweet, and was wrapped up quickly with a little satin ribbon. Too perfect to continue past its prime, I relish little gifts like these. 

Flash forward about a year and yet another opportunity for sexy diversion arose. An old acquaintance was reintroduced into my life and extreme flirting quickly turned into extreme action. Huzzah! Single, smart, creative. The sex was fantastic, the post coital chat stimulating. We clicked. This was it; it could be the perfect fling I had been waiting for. Flirty, steamy, regular. Jackpot.

If only it panned out as well.

What I always ensure after a hookup –whether it’s a one night stand or a promise to be something of substance– is to send a follow-up note of thanks. If it was indeed a very good time, it’s infused with enough innuendo that leaves the playground gate open for more fun. If the feeling isn’t mutual, it will be readily apparent in the response
(or lack of one). Easy peasy. Unless the experience was exceptionally egregious, I’ll always send that note. It’s only good manners. I am usually the first to send it.

With this latest liaison, it was like moving from the teeter-totter to that metal spinny thing that you have to push like a fiend to get any tangible result. Monosyllabic replies that I could see had some juicy potential fell flat, and though I struggled to maintain the momentum, he just couldn’t keep up. Despite a couple more energetic dalliances, I became tired of spinning and jumped off. The contradiction between the offline and online tryst was proof that despite his wanting to continue playing, he just doesn’t have the skill. I chased too much, he not enough.

So my words of advice for being a skillful flirt: 

Be clever, not lewd. Don’t send dick pics until consent for that type of shit has been established.

Don’t try to be a smartass and quote (especially incorrectly) Alexander the Great, any Shakespeare, poetry, or songs. Movies, tv or contemporary literature, however, get a pass in my book.

Be honest. If you want things to go further, let them know. If not, also let them know.

Be respectful of a person’s time. Find a balance between too much messaging and too little.

Bonus points. Try flirting offline. Prove that you’re willing to take more time with a potential playmate than you would paying your phone bill via the Rogers app.

I will be the first to admit I’m a sexual snob. I’m one with high standards and low tolerance, so finding a worthwhile playmate is not a common occurrence. When I do find someone who understands the art of being a valiant courtier, the game is certainly worth playing, and I’ll jump on every structure in the playground.

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Got a question about sex in art, relationships, parenting? Send Sonya a note at dearmadame@torontostandard.com. Anonymity assured.

Sonya JF Barnett, also known as “The Madame,” is the founder of an erotic arts community called The Keyhole Sessions and the co-founder of SlutWalk Toronto. Follow her on Twitter @KeyholeSessions. 

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