How to Send a Guy the Right Text at the Right Time

Once upon a time there was an old rule of thumb that men and women lived by when it came to dating called the “three-day rule”. If you exchange numbers with someone, wait three days to call. After a date, wait three days to email. After a hookup, wait three days to text. And so on and so on. Nowadays in our culture of technologically enhanced instant gratification, this practice has become something of an ancient artifact, a bygone ritual of the olden days.

And yet, there are plenty of women out there who still struggle with how to time their responses and reactions to guys they are interested in. You don't want to come off as too eager or desperate, but you also don't want to seem uninterested or wait too long and lose out on a promising prospect, especially when it now takes only .25 seconds for a guy to swipe right on Tinder and find a new hottie to flirt with.

There's also the admittedly first-world problem of too many ways to get in touch: Should you text, DM, Snapchat, Facebook message, send a carrier pigeon or – heaven forbid – just pick up the phone and call? And then, once you've decided what medium of communication you'll use, there's an even bigger question waiting for you: What the hell should you say?

There's a pretty easy solution that I like to apply to this triple dilemma of 1) when to get in touch, 2) how to get in touch and 3) what to say when you do. Basically all you have to do is work it backward. So instead of focusing first on question #1, ask yourself a variation on question #3: What – if anything – do you actually want to communicate to this person right now? If you have something cool to share that you think is genuinely interesting, then trust your guts, embrace your inner superhero and go for it – the sooner the better, in my opinion. Be brave but don't be impulsive, and don't over think it! If it's a message you've actively chosen and feel good about, it will come out more easily, I promise. And hopefully this will help you care a little less about questions #1 and #2.

Now, if you're not sure what to say and you're struggling to get past “hey” or “whats up” or you've spent the past hour erasing and rewriting the same message twenty times without sending it, the best thing to do is just step away from the machine: stop and give yourself a minute or an hour or a day to regroup (note how that takes care of Question #1 momentarily). Bottom line: If it ain't working, don't force it! You want to strive to convey something genuine if you want anything genuine in return.

The next thing to do while you take a self-imposed technology hiatus is gently ask yourself a few of the following questions (since you will likely still be thinking about it anyway): What do I really want to do here? What's my motivation? Do I want to share something real with this person or is sending that sexy side-boob pic with three kissing face emojis at 1.42am just an easy way to get some attention? What are some of the things that might happen if I do that? What do I want to happen? And what if it doesn't? Am I cool with that? Is there another way I could better express my interest?

Try your best to get clear with yourself on this stuff and accept all the possible outcomes: Maybe you'll find that you don't have anything to say and decide not to get in touch after all. Maybe you'll go ahead but get no response anyway. Imagining the possibilities can be a powerful way to build a sense of control and confidence over the situation. And that may eventually allow something more substantive and sharable to pop into your brain. Who knows? Maybe by then he will have gotten in touch with you and all this will be a moot point, until the next go-round at least.

What's important is to know what you want to say before worrying too much about when and how to say it. So figure that out first then make your move. Always own your decision to act and be open to whatever happens next. And remember: making connections with new people is supposed to be fun, so don't make yourself crazy! After all, it is only a text or a tweet or a pigeon, isn't it?

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Chiara Sulprizio

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Chiara Sulprizio is a dating and relationship coach who specializes in helping women enhance their communication skills so that they can improve the quality of their relationships and become more empowered. You can learn more about her services and read more of her writing at www.chiarasulprizio.com.