The Trouble With Online Dating

I’m going to tell you something that you already know: dating is a frustrating process of trial and error. For a lot of people, it’s a seemingly never-ending dance of missed connections, nights you’ll never get back again and wondering just what’s wrong with you and why everybody else seems to have it so much easier.

Even for people like me who enjoy the whole dance and the chase and the thrill of the new, there will be points when you really just want to take a step back from it for a while and catch your breath and let your ego recover from the beatings that tend to come with it.

"Hey man, i want to get laid as badly as you do, but do you think maybe we could spend a night NOT getting rejected over and over again?"

“Hey man, i want to get laid as badly as you do, but do you think maybe we could spend a night NOT getting rejected over and over again?”

Online dating is often touted as the solution to dating frustration. Screen your dates in advance! You only have to deal with people who meet your standards! Take all the time you need to craft the perfect dating message

Of course, in practice… it’s a different story. In fact, for many people, online dating is such a trial that they give up early on. But just as when you’re trying to meet your future snugglebunny the old-fashioned way1, it’s important to understand the potential headaches that come with those marathon OKCupid sessions. Many of the things that drive people away from online dating can be headed off at the pass with some preparation.

Get Out of The Offline Dating Mindset

The first step to overcoming your frustration with online dating is to adjust your mindset and expectations accordingly. Online dating takes a different attitude and skill-set than, say, making cold approaches at a bar or flirting with someone you met at a house party.

To start with, you have to rethink the way that you present yourself.

Studies show that between 75% to  93% of communication is non-verbal. When we meet somebody in person, we have hundreds of thousands of verbal and non-verbal clues to give us an intuitive grasp of who we’re talking to and whether or not we’re into them long before we go up and introduce ourselves. Everything from how they stand to how they talk, who they talk to,  how they act around their friends, how they smell, even the pitch and timbre of their voice indicate whether or not we’re likely to have an initial attraction to them that would prompt us to make that all-important first approach. We’re able to process all of these signals so rapidly that we’re often unaware of it; to our conscious mind, we’re just eliding over the ones who we read as “nope, not interested” while we narrow our focus on the people who do it for us.

All of this subconscious presentation and filtering is lost in online dating; all we have are our words and our photos, so we have to consider how to craft as attractive a snapshot of ourselves as possible. In online forums and gaming – where many people meet their partners – how we express ourselves and our personality acts as the initial attractors. Similarly, we try to divine as much of that information as possible from the dating profile photo and username even before we start in on the dating profile. This is why you have to take care to understand exactly what your profile is saying to the women who view it. It takes very little to accidentally give the impression that you’re bitter and resentful and as we all know, there’s nothing that makes panties evaporate faster than complaining about how often you get stuck in the Friend Zone.

You have to treat your dating profile as an advertisement; you are, after all, selling yourself to others. This means that you have to consider your market, what you’re looking for and what makes you, specifically, attractive to others. OKCupid, for example, is structured more heavily towards casual dating and hooking up., on the other hand, leans towards more conventional relationships while eHarmony is specifically marketed towards (straight) people who are looking to get married ASAP while Plenty of Fish is the dating equivalent of a long weekend in Innsmouth.

"I like sunsets, sushi, long walks on the beach and eviscerating outsiders in the name of Dagon."

“I like sunsets, sushi, long walks on the beach and eviscerating outsiders in the name of Dagon.”

You also have to consider where and how to present your best self. If you’re the sort of person who’s clever and witty, then you want to look more towards a site like OKCupid that lets you display your humor like the tail of an Oscar Wilde-loving peacock. At the same time, you’re less likely to  have success when dealing with dating/hook-up apps like Grindr or Tinder. You’re going strictly by photos; you only have a chance to wow them with your wit after they’ve decided you look fuckable.

Play The Numbers Game

Speaking of the offline dating mindset: you’re going to have to accept that online dating is even more of a numbers game than dating in IRL or meatspace or whatever the cool kids are calling “the world” these days. This means sending out more cold e-mails, dealing with more rejections and more dates that go nowhere.

Sorry. It’s part of the price of entry, and it’s better that adjust your expectations accordingly instead of dealing with the slow burn of “WHY WON’T THE MAGICAL BOX PROVIDE ME WITH SEX?”



Remember what I said earlier about how we mentally filter people into “attractive” and “not attractive” when we meet them in person? The lack of non-verbal cues that attract us to others don’t carry across in online dating and, as a result, you’ll occasionally come across people who seem great on paper but who don’t turn you on in person. We can get as righteous as we’d like about “getting to know somebody’s soul” or the purity of meeting people without our hangups about looks, but without that physical component, it’s impossible to guarantee that you’re going to be attracted to somebody in person. This is why so many people get first dates that go nowhere; you may have had great intellectual or emotional chemistry, but physically, it just wasn’t going to work.

And the answer to this is, simply: date more. And that’s where the benefit of the numbers game comes in.

Many people treat online dating as though they were talking to somebody in a bar. In the physical world, unless you’re Jack Harkness, flirting with several different people simultaneously is a major faux-pas and likely to leave you going home alone – possibly wearing several drinks. We often carry this mindset over into online dating and start to give one person – usually the first one to respond – all of our attention, ignoring everybody else until that first conversation has run it’s course.

This is a mistake – and one that makes online dating considerably more inefficient and tedious. One of the advantages of online dating is that you are capable of carrying on several asynchronous conversations, fielding responses from persons X and Y while also sending out an introductory message to person Z. You can and should cast your net far and wide. Focusing on one single person – even if you’re at the “meeting in person” stage – puts far too much importance on them and makes it sting worse if it doesn’t work out the way you’d hope. You want to be using a shotgun, not a spear.

Show, Don’t Tell

Of course, before you can get those dates, you have to make your profile stand out the right way. Most people who have trouble making  online dating work for them make the cardinal mistake that gets drilled into anyone who’s ever taken a basic creative writing course: they’re too busy telling about themselves instead of showing. Some of the oldest and most boring cliches of online dating are the people who just say that they’re some attractive quality… without anything to back it up. Saying that you’re funny or spontaneous or romantic is the dating site equivalent of “I listen to a little bit of everything except country and rap.” It’s so generic as to mean nothing. Everyone has heard it a thousand times before they saw your profile and they didn’t believe it any of those times either.

In the great chain of credibility, being told something is the least believable. Having a second party tell vouch for you is more believable, but being able to show that quality is instant credibility. I could say I’m Dr. NerdLove, Millionaire and that I own a mansion and a yacht and most folks would brush me off.

Seems legit.

Seems legit.

On the other hand, if your friend tells you about the incredibly lavish party they went to at NerdLove Manor (aka: the Gatsby Gambit) last weekend, you’re more inclined to believe that yes, I am a millionaire with a mansion and a yacht. And if I happen to sail past your house – which is quite the feat when you live in the middle of a land-locked city, let me tell you – then you’re far more likely to believe.

This is why you want to demonstrate those qualities, to the best of your ability.  And since you’re dealing with dating profiles, that means using your words… and your pictures.

Take humor for example. Everyone claims to be funny in their profile and most of them are as dull as dry toast when you meet them in person. If you want people to believe that you’re a laugh riot, you have to show them. If you have a sharp wit or a way with words, work that into your profile. Don’t call attention to it, just work it into your “About Me” section or “What I’m Looking For”. If your brand of humor trends to the physical or being silly, then post that picture of you as the Stay-Puft Marshmallow Man from last Halloween or doing something wacky. Telling somebody you’re adventurous is similarly unhelpful. Better to talk about your recent trip to Ankor Wat or – even better – have a photo of you in front of Ta Prohm. Don’t say that you’re athletic, mention that you take part in an amateur soccer league or have a cool photo of you and some of your teammates after your latest scrimmage.

Remember: the web is a visual medium. Photos that back up what you say in your profile will give you more appeal – and credibility – than just saying something.

Speaking of:

Appearances Count

I’ve gone on about the importance of dating profile photos before. These are going to be the corner stone of your time in online dating. People are going to look at your photos long before they bother going through the rest of your profile. If your photos look like somebody accidentally snapped your photo while trying to find Bigfoot, they’re never going to bother with the rest of your profile.

"Wait, I'm confused. Is that his face or a goiter?"

“Wait, I’m confused. Is that his face or a goiter?”

I’m a big proponent of putting your time and effort in the areas that will give you the most return for your investment and in online dating, that’s your main profile photo.

If you can manage it, I strongly recommend having a professionally done headshot for your profile. Failing that, have a talented friend take a few for you. You want something that’s going to entice people to click through to your profile when they’re searching for matches or when your email shows up in their inbox and the more they have to squint, tilt or otherwise try to interpret what they’re looking at, the more likely they are to just move on to the next person on the list. Just remember that you want something that shows a little of your personality, not something that looks like Picture Day in junior high.

You want your main photo to stand out from the crowd. A simple background puts the emphasis on you and makes you pop. A splash of color – a brightly colored shirt, for example – will also catch the eye, especially when compared to the mirror-selfies and the washed out party snaps that seem to populate every dating site ever. Let the rest of your photos be candids, but be sure only to pick the ones that you look good in. I’ve lost track of how many people I’ve seen who’ve posted awkwardly angled “cool” shots that ended up giving a great view of their nose hair and derp face.

Also: when in doubt, leave the flash off and opt for indirect lighting. Direct lighting, especially overhead lighting is nobody’s friend.

He Who Hesitates Is Lost

The number one complaint I get from guys who’re frustrated with online dating are the conversations that start strong and then suddenly she pulls the fade-out. Those long emails back and forth get shorter and shorter until you’re just getting one or two sentences back… at best. Then… silence. Meanwhile, you’re left wondering just what the hell happened and whether or not you should message them again.2

Almost every time I’ve seen this happen, it’s been because the guy took too long to get to the point. They get so caught up in trying to impress their digital coquette that they forget to, y’know, actually ask them on a date.

"Oh. Right. That."

“Oh. Right. That.”

The point of online dating is, y’know, the date. I can understand wanting to make sure there’s some chemistry or not wanting to seem too eager (or desperate), but the longer you take to getting around to actually asking her out, the more likely that either a) she’s going to assume you’re not interested and move on or b) somebody else is going to ask her out first and that guy is going to get the lion’s share of her attention. You can’t just assume that she’s going to be the one to suggest a date; you’re going to have to be willing to be proactive here.

The longer your conversation goes on over email, especially a dating site’s email system, the more emotional momentum you’re bleeding and the greater the likelihood that you’re never going to actually see them in person. You always want to be moving up the communication intimacy ladder. Email on a dating site is about as low-investment as you can get. If you’ve had three to four quality emails back and forth, you should be trying to set up a date. At the very least you want to take it off site – ideally to text or actual phone-calls, but at least to some form of instant messaging. Constantly just swapping messages back and forth gets you nowhere and ultimately just wastes your time. It’s online dating not online pen-paling, after all.

At the same time, sometimes things are just never going to go anywhere. Not getting a response to your latest email is a response: they’re not interested. It’s better to give them up for lost and look elsewhere. Similarly, if you get the sense that their interest is fading or that they’re just being polite by responding – cut them loose and move on to somebody else. There’s no profit in riding that bomb all the way down; it only makes you feel worse about yourself and takes up time needlessly.  You should have better things to do than get hung up with a relative stranger, including messaging other, more likely potential dates.

Remember: dating is supposed to be fun. In the end these are fairly simple adjustments to make that help eliminate the majority of frustrations with online dating. And the fewer headaches you have to deal with, the more you can actually enjoy being single.

  1. via arranged marriage! None more traditional! []
  2. Spoiler alert: no, you shouldn’t. []