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A Gentleman’s Guide to Sexting

Tiger Woods

And now for some wise words of advice from Kempt’s resident phone etiquette expert and certified lady-person, Michelle Ong.

Let’s get one thing straight: nothing ruins romance faster than a bad sext.

Even a perfect date can be spoiled if your best-intentioned goodnight message turns into a slightly vulgar description of your “peepee”—or worse, a deluge of winking emoticons and a picture. Ugh. Sure, the standards of courting a lady online aren’t much different from doing it in real life these days, but sexting comes with its own nuanced set of rules.

Here’s how to go public with your privates... gracefully.

Don’t do it if you haven’t actually done... it. Part of the excitement leading up to a first date is the whole “does he like me, doesn’t he like me” mental gymnastics thing that our brains will flip through. So keep your texts flirty but casual, and steer clear of the “Let me tell you what I’d like to do to you” zone... for now.

For the love of God, no emoticons. It’s cheesy as hell, and comes across as lazy (or stupid). Remember that you’re aiming for the eloquence of a Harlequin novelist (let’s ignore the fact that they’re usually middle-aged cat ladies for a second)—so don’t use a cartoon to express something you should be saying with words.

... nor “dick pics.” I know you think there’s nothing sexier than an expertly angled photograph of your towering monument, but 99% of ladies agree that private parts look better when they’re not illuminated by the alien glow of your camera flash.

And avoid “pulling a Weiner.” In other words, don’t be stupid—cover your trail by deleting after sending, and don’t post a sext anywhere remotely public (such as Twitter). Bonus: you won’t have to cringe when you scroll through your texts an hour later.

After all, you’re trying to seduce—not shock. Yes, you’re trying to electronically verbalize how much you want me. Yes, that means you should be using powerful adjectives to convey your insatiable desire. But there’s a fine line between “I want you badly” and “I want to cut your skin off and wear it to my birthday party.”

— M.O.