How to Sext Like a Gentleman (Heterosexual Edition)

Eight Hard and Fast Rules for That Most Slippery Form of Interpersonal Communication

By Sam Eichner ·
Photo: michaeljung/Getty Images

Given that an estimated 92.5%* (*made-up statistic) of all interpersonal interaction now takes place on a digital platform, we regret to inform you that “sexting”—i.e. sex via text—is a more vital form of communication that at any other point in human history. What a time to be alive.

But not to worry. Like sex itself, sexting can be fun, provided it’s done respectfully, thoughtfully and not while operating a moving vehicle. Just in case you’re looking for some assistance, though, we’ve compiled a list of rules (and accompanying examples, thanks to Geoff Rynex, fellow editor and good sport, who will be playing the female role) everyone should follow in order to sext like a gentleman.

If such a thing is possible. Which it is. Right? Right.

1. The intensity with which you sext should be more or less commensurate with the stage of your relationship.

By which we mean, you shouldn’t really be telling someone how much you want to be inside them if you’ve only shared a chaste kiss goodnight. That being said, sexting can be an important seduction method, used to inspire longing in whoever you’re seducing. If you’re on the cusp of sleeping together—maybe you’ve already been on a few dates, and have been some degree of naked in each other’s presence—you should feel free to wade into sexier waters. But if you’ve just started seeing each other, maybe stick with “I can’t wait to see you again” or something that doesn’t involve you discussing your genitalia.

2. Know your audience.

Know her likes, know her dislikes and, perhaps most importantly, know her boundaries. Some women are going to be more accepting of your sadomasochistic emoji porn than others. When in doubt, err on the side of caution.

3. Escalate slowly.

Again, think about this like real sex. You wouldn’t whip out your dick before you started making out with someone, would you? Try something relatively innocent and sweet first (“I want to kiss you, again”), then move on to the more risqué (“[redacted]”), noting how she gauges each response along the way.

4. When at all possible, let her initiate.

Give a man enough rope and he’ll hang himself. Give a woman enough space and she’ll take sexting to a new level. This is a very problematic and imperfect metaphor. And yet, apt.

5. That said, sometimes you've got to step up. 

Don't assume your possible beloved will start things. At a certain point, there's an element of cowardice and awkwardness in waiting that is sure to send the whole thing down a catastrophic path. When you feel the tipping point coming, think of an elegant sext to send. Then, don't send it. Then sleep on it. Does it still seem like a good idea? If so, send away. If not, think of a new one and repeat the sleeping-on-it process. If you're stuck, remember, innuendo is your friend. Just use it with humor, not perviness. 

6. RE: Emojis

Dos: Facial reaction emojis, lipstick emojis, hand slap emojis, any and all heart emojis. Don'ts: Animal emojis, fist emojis and the poop emoji. Caveat: There's an exception to every rule. We're not sure we want to know what that particular exception would be.

7. Never send a dick pic unprompted.

We would say “never send a dick pic, period” but since the invention of the camera, dudes have been taking pictures of their dicks to send to girls. It’s become biological imperative. It’s the modern equivalent of Vincent van Gogh sending his ear to his beloved, except also not that (though, really let that gesture sink in). So let this be the rule you live by: don’t send a dick pic unless expressly instructed to do so. Or just don’t send one at all. Because unless you’re a legitimate photographer, or a porn star, or both, your dick probably won’t translate well to the notoriously inartistic medium of amateur iPhone photos. 

8. If prompted, remember the "death from above" principle.

Foreshortening contains the word "shortening" within it, and it's real

Sam Eichner


Elsewhere on the Daddy

More Entertainment