A Gentleman's Guide to Kicking Game on the Internet

Internet wooing doesn't have to be a nightmare. Unfortunately for women everywhere, online douchebaggery is far too prevalent. It runs rampant and largely unchecked, lurking in every corner of the web, waiting to pounce on every available (or unavailable) woman with a Facebook account and a Twitter handle.

But we're here to reassure you: You don't have to join the inept masses who unwittingly repel women. You can successfully meet a lady with only your laptop and few keystrokes (in your pajamas even!) and we're here to tell you how.

Hold off on sending that unsolicited Facebook poke, and hold on to this: A Gentleman's Guide to Kicking Game on the Internet.

Your opening line should never include anything regarding her appearance. Aside from being rude and completely unoriginal, it's redundant. Most women will assume that if you're taking the time to message them (or @ reply them, or initiate any other sort of unsolicited contact) you find them attractive.

Because, really, how often does a stranger get in touch with a woman because he thinks she would make a cool, new friend? If your first point of contact is a cheesy compliment, ladies will assume you only got in touch because you think their vagina would make a cool, new friend.

That said, your main goal should be to show interest without being desperate, pushy, or creepy. Doling out compliments like "Shawty U is fine" or "I just had to tell you how sexy you are" have never—in the history of the Internet—been a successful route to capturing a woman's attention. This approach only incites boredom or anger. Sorry, dudes. You can (and have to!) do better.

When approaching a woman you have never met in real life, always ask yourself: "How creepy am I being right now?" More often than not the answer is very.

We want to believe you're a handsome, well-meaning guy, and not a 50-year-old toothless cretin with demanding kinks, but we've seen too many movies and heard too many horror stories to give you the benefit of the doubt. Until proven otherwise (as in, face to face), you are Patrick Bateman (though surely not as attractive).

Creepiness isn't just a "stranger-danger" issue—even men in her inner circle can create a aura of skeeviness. Before making your move, consider where you may fall on her creep spectrum.

Most creepy:

Medium creepy:

Slightly creepy:

Being aware of where you might fall on this creepiness breakdown and taking any apprehensions you may be creating into consideration when you first approach her—these are the first steps to getting her to take you seriously.

The best way to lower her inhibitions about talking to a stranger is to get a mutual friend to introduce the two of you (then you're not a stranger!). If you're cruising your Twitter or Facebook feed and you see some random cutie in a photo with one of your boys, don't immediately send her a friend request or a random message. As discussed, a compliment as an introduction is an always-fail approach, and "Hey, how are you? I don't know you but...you seem cool" isn't much better. What are you basing this on? The three small tidbits of info about her that Facebook hasn't blocked? Sure, it's nice to think that we seem that intriguing based on the single sentence bio Twitter allows, but it's just not possible.

Ask your mutual friend to find out if she's single and possibly set you up with her, even if it's just a casual group meeting at a local bar. If your mutual friend thinks highly enough of you to vouch for you (and reach out on your behalf), you've nullified any potential creepiness; in fact, you've actually won a few points.

In an ideal world, every beautiful woman you came across would be a friend of a friend. But the fact is, some of the people we stumble upon in the seemingly infinite universe that is the Internet are total strangers.

That's not to say you can't be genuinely attracted to the identity someone has constructed online. If you consider the many mediums we use to connect these days (Twitter, Tumblr, Pinterest, Formspring, Wordpress, LinkedIn, gchat, Foursquare, YouTube—the list grows faster than we can create new profiles!), you realize that you can get a multi-faceted sense of who someone is. Still, it's just a constructed outline, one that has probably been built with an audience and desired self-image in mind.

And yet, you should give thought to what your many social medium platforms have to say about you. If your Twitter handle is SuperSwaggerMan and your constantly @-ing other girls—"Hey sexy, follow me back xo!"—the woman you reach out to will size you up in a single click, and in that click, you'll lose your chance.

Similarly, if you post explicit images on your Tumblr, have an entire board devoted to "Big Booty Bitches" on Pinterest, and ask random women with bra-shots as their avatar personal questions on Formspring, you're communicating something very specific about yourself, and you're broadcasting it to every prospective new woman you meet out there.

Reevaluate your online persona from a woman's perspective. Are you someone who seems genuine and interesting, someone capable of being honest and trustworthy? Is your internet identity an accurate representation of who you are, or is it a cleverly constructed stand-in for the person you'd like to be? Do some serious editing so that your social media presence works for you, instead of against you.

The medium is the message when it comes to contacting women online, meaning your approach should be tailored to the pathway you'll send it along. For example, the message you send to a woman on Match.com will be different than an @ reply on Twitter, a message on Facebook, an "ask" on Tumblr, et cetera. The method of communication is as important as the message itself. Form is content, fellas.

Facebook is typically the most personal medium because of the level of access, the quantity of photos shared, and the fact that many people's families interact with them there. That's why unsolicited Facebook friend requests will often go ignored.

On the other hand, platforms like Tumblr and Twitter are crafted for the eyes of the Internet at large, and in most cases, interacting with strangers within those communities is the norm. In other words, your random message won't be perceived as out of the ordinary.

Consider the woman in question before choosing your means of contact. Also, notice we said "point" and not "points." It's quality of communication, not quantity, that will get you noticed. Don't go on a Google rampage and start following her every social network profile. That will not land you a date—it will land you a restraining order.

The Internet, though riddled with booby traps for men on the prowl, offers unrivaled opportunities to win over a woman before ever meeting face-to-face. With all of the information available to you about who she is and what she's interested in, you have literally been handed a field guide to establishing common ground.

Instead of making like Woody Allen in Everyone Says I Love You and using the information you have to pose as the man of her dreams, look for ways in which you can genuinely connect. If she's tweeting about Kendrick Lamar's latest track, share your opinion about it, even dare to disagree with her. It's not about seeing eye-to-eye right off the bat, it's about starting a conversation. It's more likely a woman will become intrigued by a guy who interacts with her on a regular basis and actually has something interesting to say.

This is exactly what women are looking for: a man who is genuinely interested in who she is and what she has to say. Rather than commenting on her profile photo, say something about what she devotes her time to online. If she always makes comments on current fashion trends, give her props on her good taste. If she takes great photos, tell her she has a great eye for landscapes (or whatever the subject is). If she keeps a blog, tell her you read it and mention something specific you liked about it.

Actually read it.

Find something that you admire, don't send a superficial compliment. An in-depth assessment will really get a lady's attention, because it shows she's really got yours.

Many an online faux pas can be avoided by considering the following: "If this woman was in front of me, would I act the same way?"

The application of this is endless. If a beautiful woman was right in front of you, would you ask her for a nude photo? Would you play it cocky and say, "I usually only date blondes, but I guess I can make an exception for you"?

Please, be you. Don't exaggerate who you are, even about little things, like your interest in Charlie Kaufman films. Having seen Adaption once hardly makes you a "big fan." Keep it real.

A few last things to keep in mind:

Gentleman, good luck navigating the very-tangled web! We hope our advice lands you exactly where you want to be: offline, and in-person with the woman of your (Internet) dreams.