A girlfriend of mine in her 30s was set up with a guy. He checked her out on Facebook. She did the same. Then they both gave the okay to their mutual friend and a slew of emails followed, in which they got to know each other a bit before setting up a date. The communication started out promising. Then, she tells me, it eventually became “less English, more teenage shorthand.” Here's a sampling:

how r u,

what up? cn u mt stday nite?

This is a man who is 42 and runs his own venture fund.


Do not underestimate the power of language.


In one way or another—via texting, tweeting, or in real life conversation—we are all guilty of the occasional “obvi” or “totes.” But assuming that you’re a grown man who likes to read a quality magazine (hi, Complex fans!), or appreciates a good beer or well-tailored blazer, then you have great taste. Why ruin that by texting like a 15-year-old?

Unless you’re being sarcastic, or perfecting your imitation of younger relatives, there is no reason to use “like,” “awk,” “ridic,” or anything similarly dumb when communicating with a woman you want to date.

Before you shrug your shoulders and mumble “Whatevs,” it’s worth considering (again) that women will equate much of what you do with how you’ll behave in the bedroom. While many of us want a guy who’s familiar with the slang and pop culture references of the moment, actually using some of this shorthand is as misinformed and misguided as your first kiss.

Slurp. Drool. Ouch.

But everyone’s doing it. Is that what you’re thinking? Yes, everyone is doing it; you’re right. But no one who is getting to know, trying to impress, or keep a woman interested should be. Part of being a better man—better than the other guys at the bar and better than the massive field of singles on various dating sites—is recognizing the difference between looking cool and looking like an adolescent.

Do not underestimate the power of language. A woman falls in love with her brain, which is why proper grammar, punctuation, and spelling will often times get her to dinner (and by proxy, bed) faster than a solid set of abs or fancy suit. Though neither of those hurt.

You remember the time a guy signed a letter to me with a heart? (How could we forget?) Just as cringe-worthy is signing off with an “XO.” Amongst girlfriends, this salutation is warm and appropriate. When it comes from a man… well, let’s just say the only time you should be using “XO” is when ordering food in an Asian restaurant.

And don’t get me started on emoticons. I have lectured many a male friend on the (ab)use of smiley faces and their ugly cousin, “LOL.” Women are smart. We can tell the difference between when you're kidding and when you aren't. If you need to use a colon and parenthesis to show you're being sarcastic or facetious, or worse, that you're flirting with us, then you deserve to be single.

Slurp. Drool. Ouch.

I am willing to concede that I have a particularly strong gag reflex when it comes to “LOL.” I am also willing to admit that there is nothing a woman wants more than for a man to laugh at her jokes. But, please; I beg of you: When a woman says something funny, please do not respond with “hahah” or “LOL.” Instead, do better; say something funny back! Keep the banter going and I promise she will choose you over those other emoticon-using chumps.

I understand that we live in a world where texts fly fast and furious, unread email counts in inboxes climb higher than the steamy temperature outside, and a certain social medium only allows you 140 characters to articulate your message to the world. But there is a fine line between using modern technology for enhancing communication and becoming a slave to its jargon.

So think about your audience and think about your message. If you want to convey to a woman that you are an intelligent man worthy of her time and affection, then please email, text, and speak like one. You won’t attract a smart, savvy woman communicating like a teenager.

As my girlfriend navigating emails with a 42-year-old kid can attest, when you ask “cn u mt stday nite?” in the shortest amount of characters possible, I’m afraid you’re going to get a response with, you guessed it, the shortest amount of characters possible.


In Two Weeks: Is age really just a number?