Navigating The World Of Online Dating

Dating can be difficult, but the online version has its own set of quirks, rituals, and pitfalls. Here's our guide to navigating them.

Don't stress too much about your profile.

Of course, the first step in online dating is the profile, and there are a million people out there eager to tell you how to do that, often for a fee. Our take: just keep it simple. Be honest — especially about what you're looking for — but don't feel like you have to write your entire life story. Don't try to be funny unless it comes naturally, either — just express some things you think are important or interesting to know about you. We can't guarantee that this approach will immediately get you nine zillion dates, but it will allow you to start the process without tying yourself in knots about the best possible thing to say. Regarding photos: OkCupid has a bunch of data on how things like camera and time of day affect your pic's attractiveness to other users, but thinking about this stuff too much is a good way to get stalled out and never start dating. A simpler approach is to get a friend to take a nice, current photo of you, so you don't have to crop out other party guests or whatever. Unless you're one of those people who looks effortlessly awesome even when caught off guard, this will probably look better than a candid — and having a photo you like will make you feel more confident and relaxed about the dating process.

Pay attention to other people's profiles.

I talked to Virginia Vitzthum, author of I Love You, Let's Meet: Adventures in Online Dating and My Blind Date Went Blind, who says, "It boggles my mind that guys send these form letters. 'I am a fun, caring guy....' and you have no idea if they read your profile. Or guys that boast that the profile means nothing to them, they just like your picture." And indeed, the overly-generic message — one that doesn't mention your profile at all or merely says "I liked it" — suggests that the person isn't really interested in you specifically, which is never flattering. Instead, suggests Vitzthum,

[T]ailor your reply to their profile. Say that you too love that book, movie, band they love (but only if you really do) and then add something intelligent about it. Kind of triangulate passion onto a shared object. If they made a good joke, riff on it. Taking off from their profile is flirting without being overtly sexual.

Give a thoughtful compliment.

Cheril Clarke, author of Love and Marriage: The Gay and Lesbian Guide to Dating and Romance, told me,

Always throw in a compliment or two. Who doesn't like a good compliment? But try to be a little different. For instance, avoid telling him or her how "hot" or "beautiful" they are, compliment them on something they wrote in their profile or an apparent personality trait they portray. This will make you stand out from the rest because it shows you are able to connect below the surface (and that you actually READ vs. just looking at pictures). If you want to compliment them on their physical appearance, try bringing positive attention to a facial feature, rather than writing the common "you're beautiful" comment. An alternative is to state that the particular color they're wearing really makes them look radiant (only if it really does).

Telling someone he or she is hot can come off as generic (see above) or even creepy. You're much better off with something like "you have great taste in movies" — which can also be a jumping-off point for future conversation. Speaking of which...

Ask a question!

This is key. Asking questions helps keep the conversational ball rolling (until you're ready to meet in person, that is). It can be hard to know how to respond to a message that's just a bunch of statements, but a question opens an easy avenue for a reply — and you want to make replying easy. Suggests Clarke,

You always want to show interest in who they are what they do or are passionate about. You can ask questions about their line of work, what they're studying or what otherwise gives them joy (something that is not answered in their profile or something that is only lightly touched). This will prompt conversation as people usually have a lot to say about their line of work or school. If they have children, ask about that, but not too personal. Don't be creepy. Make sure you give information as you are asking then questions too. End with a question.

She adds a couple of caveats: "Avoid questions that only call for a yes or no answer" and "Be careful not to ask too many questions." People need to know you're actually interested in learning about them, but, as Clarke says, "no one wants to feel as though they're being interrogated."

Don't be a creeper.

Online dating sites can be a little scary, especially for women. While in-person dating carries plenty of hazards, it's true that being online ups the sheer number of pushy, creepy, or otherwise unsettling people who might have the ability to contact you. Lessen the scariness for everyone by following a few simple rules, as spelled out by Clarke:

Don't talk about sex and don't say "we have a lot in common" without being specific. Have some depth to your message. Avoid questions about their physical features (weight, size, build) right off the bat. You should be able to see all you need to see from a person's photo. Never ask to meet in the first message. That's a no-no and a clear sign to the other person that they should run, not walk away from you. Don't ask for their phone number in the first message or their real name.

The "don't talk about sex" tip may not apply if you're on a site specifically devoted to sex, but otherwise, it's definitely a good rule of thumb. Clarke also adds this key tip: "don't be a stalker. If you don't get a response, move on." Nobody owes you a message, and repeated — or angry — messages after non-response are invasive and creepy.

You don't have to respond to every message.

It's not the nicest thing in the world, but online, simple non-response is the accepted way of dealing with an initial message from someone you're not interested in. You don't have to say, "I don't think we're a match" or anything like that — and in fact this sometimes makes people mad. Just ignore. However, Virginia Vitzthum advocates a little e-breakup if you've been messaging with someone but don't want to continue:

[O]nce you've back-and-forthed, I think you should extinguish hope, even if it's with a gentle lie like "I realize I'm not ready to start dating again." Of course they can then see you're back on the site that very day, but at least they know to move on.

All that not-knowing and fading possibilities make people feel horrible. All the online daters are in it together, so why not make it as clean and pleasant an environment as possible? The creeping malaise from online dating doesn't come just from "everybody else is a schmuck"; it's also "I'm turning into a schmuck." Don't be a schmuck.

Don't be embarrassed about dating online.

Some people may turn up their noses at online dating, but their numbers are shrinking — and they really don't have a good case. Says Clarke,

You really know no more about someone you meet for the first time in person than you do someone you meet online for the first time. In both situations, you have no idea if they are sane or crazy. I don't think there is any shame in online dating. Although my wife and I met for the first time in person, the majority of our getting to know each other took place online through instant messaging. Sometimes physical distance can make seeing someone you're interested in a challenge at first. Why not use technology to help you out?

Adds Vitzthum,

Is it more wonderful to fall into relationships organically in the real world while doing something you like to do? Duh! But for whatever reason, that is not happening for a lot of people. So I'd ask the critical, nosy people if they think it's better to just pine your way through a dry spell.

For one reader, these critical people are her dates, who frequently ask her how much she dates online. This may be their own insecurity (dudes, get over it!), or it may just be an awkward ice-breaker, but it's not a question anyone should feel they have to answer. Be honest if you feel like it, or say something like, "oh, I've tried it a bit," and move on. Anybody who is prying or judgy in this area is probably not worth talking to.

Don't email forever.

Says Vitzthum,

My book I Love You, Let's Meet opens with my making the classic rookie mistake of e-mailing too long and creating a person in my head and being horribly disappointed when we finally met. And I've heard that more than any other narrative from other Internet daters. So I am a big believer in get-to-the-date after a couple back-and-forths. There is generally nothing to be gained by protracted e-mailing or phone calling with a stranger.

That said, one phone call isn't a bad idea, especially if you're someone for whom voice is an important part of attraction.

Obviously, you want to talk enough — over email, message, or phone — so that you feel comfortable meeting the person (and regarding safety, check out our first-date safety tips). But talking too much online before you ever meet incurs the risks Vitzthum mentions — and it also takes up a lot of your time. Meeting face-to-face can tell you a lot about someone that a bunch of emails won't, and you don't want to sink too many hours into composing witty messages to someone who isn't a match in person. So as soon as you've exchanged a few messages and there's interest and a certain degree of comfort, schedule a real-world meeting. Then your online dating experience will become just dating, which has challenges (and joys, really!) of its own.

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I Love You, Let's Meet: Adventures In Online Dating
My Blind Date Went Blind
Love And Marriage: The Gay And Lesbian Guide To Dating And Romance

Image via Lasse Kristensen/Shutterstock.com