Ask An Adequate Woman is a space where folks can ask the questions they can’t—or maybe just won’t!—pose to their friends about relationships, fashion, family dramas, dating, existential crises, weird sex stuff, and everything else. The Women of Deadspin (and some of our clever friends) are here to happily lend an ear, and share some thoughtful advice. We want the best for you, bud. Got a question? Here’s our email.

Our first question comes from Mike:

How do I sext a girl that I’ve been hooking up with or dating for a few months now? She’s mentioned it in conversation before. I don’t want to be a creep, and it’s really awkward to do it out of the blue. Any advice on how to get started?

This is a question of when, rather than how, to sext, but it’s sensible to start by thinking about what you might say when you do decide to break the ice; not least so that you can avoid some of the common pitfalls that tend to plague men in particular when it comes to sexting. For a start, guys tend to overdo the adjectives when it comes to style—“I can’t wait to see your tight wet moist cavernous ...” STOP RIGHT THERE, DUDE! — and they also have a propensity to go from 0-100 real quick in terms of substance. (Example: “Hey babe, how are you? I can’t wait to [CENSORSHIP NOISES] your [BEEEEEEEP] with my hard f****** [REDACTED] when I see you.”) Unless you are 100 percent certain that your girl goes wild for talk like that, something that front-loaded is unlikely to appeal as an opener, so start subtly.

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I’m going to throw an idea out there: Are you even sure it needs to be you who breaks the ice? Sure, we’re marinating in social narratives insisting that men are the pursuers and women are the bashfully pursued, but it’s also 2015, and presumably you’re dating a grown-ass woman who is capable of spilling some filth in iMessage if and when the mood strikes. I’ll defer to your superior knowledge of your own relationship here, of course, as she may be waiting patiently for you to take the plunge. All I’m saying is to be open to the idea that she might surprise you and take the lead on this; even consider that perhaps, inconspicuously, she already has. Consider the subtle sexual signals women send: the flirty eyes and the other 30,000 non-verbal signals that it’s okay for you to talk to them before you brave it and come over to make the “first” move!

In this case, I think your girl has already given you a fairly clear signal that she’s at least open to the idea of sexting, and maybe she will ramp things up to actual sexting (as opposed to dancing around The Topic of Sexting) in her own time. If you really think it’s on you to move this to the next step, though (and soon), then there’s nothing stopping you doing so straight away. Sexting works the same way sex itself works: You do it with someone you like and respect. You get to know what that person likes by putting out a suggestion, looking and listening carefully to the feedback, going a little further, and easing off if you notice that you’ve lost her enthusiasm.

A fairly safe opener, if you’re looking for a specific way in, is to allude to some especially good physical sex you’ve already had. (Although you should start off in vague terms—“I can’t stop thinking about what we were doing last Wednesday night,” for example). Her response will immediately show you whether to go on. (“Oh man, yea, that was so hot” means that you should; “Haha! Hey so I’m at work” calls for a swift subject change.) Bold as it seems, if you think a more direct approach would go down well, you should go for it. Why not say something like, “Is there anything you’d like to do in bed that we haven’t done yet?” or “Do you know what I’ve always wanted to try with you?” So long as you have the green light, you can (slowly) springboard from there into unexplored terrain and still-secret fantasies, making sure that your girlfriend is signaling her continuing enthusiasm all the way. Good luck!


Madeleine Holden is a lawyer and writer from New Zealand who is currently based in London. You can follow her on Twitter here.

Illustration by Tara Jacoby.

Adequate Man is Deadspin’s new self-improvement blog, dedicated to making you just good enough at everything. Suggestions for future topics are welcome below.

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