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‘Sexting’ is one of those words you’re probably really tired of hearing. Not least of all because you’re wondering how you can get in on the action. Sexting by itself isn’t a bad way to spend your time—especially if it happens to be with Rihanna—but if you’re like every other red-blooded male, you’re eventually going to want to turn it into the real deal. Here’s your step-by-step guide.

1. Start Slow
Yes, there really are guys who are going to straight send a girl a crotch shot right off the bat. You don’t want to be that guy. It’s not that we don’t think your mighty meat saber isn’t impressive enough to warrant her attention; it’s just that she’s more into you than your package itself. So slow down there, Tiger. She’ll want to see it eventually. Instead, start with casual flirting and playful banter, just like if you were chatting in a bar.

Feel free to use jokes and innuendoes to wade into the good stuff, and remember: in this situation, it’s always better to ask for forgiveness than permission.

2. Push the Envelope
This might seem to contradict the last point, but it’s all about finding balance. It’s up to you to gradually turn up the heat. You do that by pushing her boundaries a little, bit by bit. Don’t be afraid to be edgy. You aren’t chatting with your mother, you’re trying to get hot and heavy with the girl you’re into. Feel free to use jokes and innuendoes to wade into the good stuff, and remember: in this situation, it’s always better to ask for forgiveness than permission.

3. Calibrate to Her Reactions
Of course, pushing the envelope doesn’t mean being a total creepvert. You want to increase the level of eroticism and intimacy without making her feel uncomfortable. If she seems to be a little put off, back off a little. You don’t have to stop completely, just dial down the intensity a notch or two.  Think two steps forward, one step back. If she continues to appear uncomfortable, then it’s time to take a break. Alternately, if you drop an innuendo that can be interpreted as innocent or dirty, and she takes it the dirty route, go with it, young man.

Not exactly the response you should be aiming for…

4. Be Careful with Pics
Not to sound like your high school health teacher, but remember that in the digital age, pictures are forever and spread like wildfire. No matter how proud you are of all that time spent at the gym, you probably don’t want to be on HotWebHunks.com (we just bought the url!). If your lady is exhibiting signs of being a crazy future cat-herder, definitely do not send her a picture… of anything. If you must, at least leave your face out of it.

No wonder Anthony Weiner got in so much trouble. That resolution is horrible.

5. Walk the Talk
You should never promise anything in a sext session that you can’t deliver in real life. Honesty counts, because if you’re b.s.-ing her, she’s going to find out eventually. Feel free to be really descriptive, as you’re only working with words—no vocal tonality, eye contact or hand motions. Chicks can be just as dirty as guys, but they generally also want a man with a mind. In other words, scintillatingly clever dirty talk will blow her mind.

6. Make It Happen
All that said, sexting is only about a half-step above self-pleasuring. You want to get her doing the real thing. If you two are far apart geographically, you’re just going to have to bring this thing to its logical conclusion and hope she’s interested later. But if you’re in the same city, it’s time to steer the conversation toward your, um, male needs. Frame it in terms of ‘loneliness’ rather than getting off. Then offer to go to her. Asking her to come to you isn’t so smooth, since no lady likes to feel like a call girl. At least not on the first date.

Editor’s note: Looking for more texting advice? Check out the Spotter playlist—a series of short videos with handy tips—below.


Jordan Harbinger is a Wall Street lawyer turned Social Dynamics expert and coach. He is the owner and co-founder of The Art of Charm, a dating and relationships coaching company. The Art of Charm has an entire ebook dedicated to texting and sexting. You can find the book and more articles about texting at www.howtotextgirls.com. You can also interact with Jordan on Facebook.