Sexting Rules For Online Dating
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Sexting Rules For Online Dating
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Sexting Rules For Online Dating

How To Master The Art Of Sexting In 10 Simple Steps

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You’re a man, and you’ve got needs. Luckily, your needs aren’t so selfish: Everyone has them -- though they’re on a sliding scale, from positive reinforcement to straight-up freaky-naughty stuff.

If you’re playing the online dating game, you will encounter potential matches who fall everywhere along this spectrum, and your chemistry with each person will be a unique blend of your respective needs. However, the digital dating revolution has evolved the rules of courtship, and at some point in these “relationships” -- even the ones that start out politely -- things will escalate to freaky-naughty texting tango. Sexting is part of the chase these days, and it’s important to know how to approach the game from various angles on this dating spectrum.

“Once you’ve sexted, you can’t unsext,” says Emma Golden, the calls-it-as-she-sees-it, been-there-done-that voice behind Emma’s Thing. “You can’t be sending a dude or gal sexy pictures of yourself, then rein in the entire thing and be like ‘How’s the weather?’ You can’t go back to a completely innocent convo, ever.”

Before you venture into this point of no return, review this list of sexting do’s and don’ts so that your needs -- and hers, or his -- are all understood, and wanted.

Do: State Your End Goal

Be intentional: This person should know if your motive is a hookup or harmless dirty exchange, or if you’re still interested in dating after everything's said and done. We all know that one’s interest can be lost as soon as things climax, so be upfront: The point at which you start sexting is a great place to state your end goal. This way, nobody gets hurt, and hopefully, both parties are still on board for fun -- in person, or just via text.

To that point, once you’ve established expectations, here are Emma’s guidelines for each end goal:

  • Potential Boyfriend of Girlfriend: “Say anything along the lines of how incredibly sexy and beautiful and amazing they are, how you can’t believe whatever they sent you is all yours, that you can’t wait to see them again and pleasure them until their eyes cross.”
  • Potential Hookup: “If it’s truly just a hookup, the dirtier the sext words and responses, the better. Make him or her feel like they’re going to be the best you’ve ever had, and vice versa.”
  • If you’ve gone on a few dates and are just spicing things up: “Don’t say much besides the sweet stuff -- i.e. wanting to kiss them again or make out. A subtle allusion to how you can’t wait to get further with them could also work given the situation, but tread lightly!”

Don’t: Give Up On The Person If Met With Resistance

Sexting isn’t for everyone. And if your partner is hesitant about sexting, then it doesn’t mean he or she is any less interested in you; it just means that they don’t get the same rise out of the digital flirtation. After all, the most important thing is your in-person chemistry, so that’s where your real judgments should be made. Think of it this way: Some people are verbal during sex, and others aren’t. Among those “others” are many people who are baffled by any vocal aggression.  

“If your partner is typically turned off by sexting, then ask him or her to lead the way when it comes to sexty time,” says Golden. “Tell them it’s OK that they aren’t comfortable with it -- you were simply inquiring, and no feelings are hurt -- but that the proverbial door is always open should they change their mind. Hopefully they’ll surprise you, if only because they know you like it. If so, marry this person immediately.”

Do: Consider Where You Met

Someone you met on Match.com may want to wait longer to start sexting -- like, after a few dates, and maybe even after you’ve actually had sex. But that’s because your shared foundation is a site that is used by people searching for quality over quantity. If you met on a hookup app, then it’s probably fair game to start sexting right away. However, some people on these apps still want to be “courted” first, even with a little get-to-know-you small talk. Sexting can be just as vulnerable as actual sex, so suss it out; is his profile photo buttoned up, and is he asking you about your job? Take it slower. Does she describe herself as “a lady in the street but a freak in the sheets?” Then sext away; the door is open.

Don’t: Sext On The Dating Site/App Itself (With One Exception)

“Personally, I would never send a sext via anything but my own personal text messages,” says Golden. “Maybe that’s naïve of me, but if you haven’t graduated past messaging within a dating site or social media app, then you certainly shouldn’t be sending or receiving full-on sexts unless you’re just a dirty bird. You can flirt, but save the filthy stuff for non-app communication.”

There’s one exception, though (and no, it’s not Snapchat, unless you can both agree to avoid taking any screenshots). Certain apps -- like 3nder or Grindr -- are green lights for a zero-to-sexty rapport. It’s not uncommon to be sexting multiple people at once in these apps, but be aware that you’re not building any mutual trust with anyone, which is a big part of sexting -- and sex.

Do: Learn Your Partner’s Comfort Level

You know how we all have different definitions of “hooking up”? For some people, it’s as harmless as making out, but for others the term is used to describe intercourse. You should assume the same with sexting -- your intensity may not match your partner’s.

Let’s pretend your partner is on board for a little naughty texting. Don’t jump in with a nude photo and expect one in return. It’s perfectly OK to ask your partner about his or her level of comfort. However, hopefully you can play off their cues, too, because the spontaneity has its own stimulating value.

“If they’re being extra flirtatious or making more innuendos than usual, then that’s usually a pretty good sign that they’re feeling it,” Golden says. “But in general, don’t be afraid to just talk to them about their thoughts on sexting. If they have your ego and best interests in mind, then this shouldn’t be an embarrassing topic to bring up. Just open the floor for the conversation.”

Don’t: Send Pictures Of Your Junk

“PLEASE GOD. Nobody legitimately wants a picture of your penis,” says Golden. “I’m sorry, I know it hurts. But penises are not pretty. They’re great to see in person, if it’s someone you care for and are attracted to. But in a picture? Just…no. I think, for girls, getting a picture of their man shirtless in bed, with a soft smile on his face, is sexy as hell. Maybe his butt if he’s got a cute one.”

One exception to the dick-pic rule, though: “Posing naked in the mirror never hurt nobody,” she says. “We’ll take that if the rest of your body and face are included in that picture. But, just your isolated dick is a hard no. The thing to keep in mind here is that women are not visual creatures like men are. Nine times out of ten, we’re going to want a very descriptive, dirty sext in words from you rather than a picture. Our little lady bean is really located in our brain, ya dig?”

Do: Compliment And Encourage

“Sexting is an incredibly vulnerable act,” says Golden. “And anybody who starts sexting should respect this. I’ve had guys who have barely reacted -- wet rags, tell you what -- and others who lose their shit. Everyone is going to respond differently. At the end of the day, it’s just pictures and words. Nothing beats the real thing, so don’t expect amazing responses every single time. Just keep a high level of respect for your partner when textual stimulation occurs by sticking with encouraging compliments, like ‘OMG you’re so fucking hot,’ ‘holy shit I want to be inside you(r bed),’ ‘mmm you’re fucking killing me right now.’ Use these general expressions of ‘YES!’”

Don’t: Let Undesirable Reactions Deflate Your Ego

Everyone communicates differently via texts, and many a good relationship has suffered because of misunderstandings.

“One of the biggest risks of sexting is what it does or doesn’t do for your confidence,” says Golden. “If you don’t get the response you want and it gets awkward, you might question everything. Again, just be sure you’re engaging in sexting with someone you trust, and keep communication open. If they react differently than you expected, hopefully they’ll justify it politely, with no real blow to your ego. And never be afraid to straight up ask your partner how they feel about the sexting experience after the dust has settled. See what he or she liked, what was weird, what was exciting, and so forth. Debriefing the sext exchange will only make your communication stronger.”

Do: Revisit These Sexts For Your Own Pleasure

Aside from Snapchat screenshots (bad etiquette, bro), anyone sending you sultry photos or nasty one-liners should fully expect that you will keep the receipts. Many people use sexting as source material for masturbation -- and that’s perfectly healthy! But follow the previous rule: These sexts are for your eyes only, even after the relationship folds. In fact… especially after the relationship folds.

Don’t: Show Her/His Photos To Your Friends

This is where sexting gets tricky. You’re leaving a trail, whether you trust the person or not. (Snapchat does archive all your photos, by the way.) It’s one thing for his or her friends to see the naughty things you say, but it’s a complete violation to show their intimate, private photos to your pals. It would be humiliating for this person to eventually learn that his or her photos have been passed around, with no control over where they end up. This person trusts you; don’t challenge their judgment by being a selfish idiot.


Finding New Matches

Now that you've learned the ropes of how to sext with online matches, it's time to expand your audience. Sure, free sites like Tinder and Bumble do an OK job of checking the basic boxes that you need when it comes to online dating. You're put in touch with singles in your area, and if you both dig each other, you're granted access to one another via the apps messaging capabilities.

But if a hookup is what you're after, mainstream online dating sites and apps aren't going to be the most effective tools you can use in order to seal the deal. For starters, if you're using Bumble, you have to wait for the lady you've matched with to make the first move -- not only is it that a time suck, but once you do get in touch it's completely possible that she won't be interested in what you're putting down, so to speak. And while Tinder does have a reputation for being more of a hookup app, not everyone is on there looking for no strings attached fun -- and virtually everyone is on there, which makes it a tough space to navigate.

What's a guy got to do in order to use his newfound sexting game to get lucky? The good news is that there are plenty of sites out there dedicated to matching singles that share the similar goal of hooking up, no strings attached. Ready to get started? Here are a few hookup sites to consider.


XMatch

AskMen Recommends: XMatch has the basic functionality of any dating site in that it connects you with local singles in your area. But the presentation differs in the way it's presented -- as a "hot list" of the most highly rated singles in your area, which is curated via a member vote. Aside from the hot list, you can browse singles not only by who's nearby, but also by sexual preferences. If you're feeling too lazy to actually meet up IRL, connect with other members via web cam, or browse the group chats, forums and "Sex Academy" that the site offers. A basic profile is free, but if you’re looking to get in on XMatch’s more premium features, it's $20 a month.

Check out XMatch


FriendFinder-X

AskMen Recommends: If you're looking for a dating site that leaves little to the imagination, FriendFinder-X is bound to make you pretty happy. For starters, you can filter your matches from everything down to cup size. On the off chance that your search for a match comes up empty, you can spend the night exploring cyber sex scenarios on the site with live member webcams. Like XMatch, you can access some of the site for free, but to gain access to all of FriendFinder-X’s features you’ll need a $20 monthly membership.

Check out FriendFinder-X


Adult Friend Finder

AskMen Recommends: The best thing about Adult Friend Finder is that it takes virtually no time at all to get a profile set up, which means you can hit the ground running so to speak. But because there are so few required details for membership, the information you're able to filter potential matches by doesn't measure up to the caliber of the other two competitors. Still, the profiles are sexy and explicit, and everyone on this site is clearly there with the same goals in mind. Basic membership is free, but if you want to gain access to the interactive features on the site, you’ll need a monthly membership of $19.95.

Check out AdultFriendFinder