Crazy Hacks to Boost Your Online Dating Success

You’re picking an online dating profile picture. Which picture do you choose?

  1. The one of you dressed up and smiling at the camera.
  2. The one of you pouting at the camera in a cleavage-baring top.
  3. The one of you biting into an enormous grilled cheese sandwich.

Hold that thought. Let me ask you another question.

You’ve finally got up the courage to start making the first move online. What should your first message to a guy be?

  1. A customized message based on something he said in his profile.
  2. “Hey.”
  3. A short blurb that you copy and paste every time.

If you know your dating advice, I’ll bet you picked (a) for both answers.

It’s common sense. Of course you want a profile picture where you look attractive—but not too sexy, and definitely not too weird. Of course you should write a unique message to each guy, so he knows you’ve read his profile.

But according to Christian Rudder, co-founder of OkCupid, those strategies aren’t actually the best of all your possible options. (Care to guess again?)

Rudder was the author of the enormously popular OkTrends blog, which captivated the internet from 2010 to 2011. He turned vast amounts of data collected by the online dating site into graphs and charts that shed light on why we behave the way we do online.

What he discovered sometimes supported our stereotypes and sometimes upended them.

For example, he found that men, no matter their age, like the look of women in their early twenties the best. Women’s tastes change over time. They prefer men who are about the same age they are.

On the flip side, most men are smart enough to avoid messaging much-younger women. They may admire youth, but that doesn’t mean they end up in relationships with a large age gap.

Rudder also found—as you’d guess—that exceptionally beautiful women get an exponentially higher number of messages than anyone else.

But here’s where things get REALLY interesting…

Rudder discovered that women who inspire both love AND loathing get a lot more messages than generically attractive women.

When it comes to getting approached by men online, you’ll have more success if you appeal to a niche group of men who absolutely love the way you come across in your profile photo…

Even if an equally high number of men find your profile picture utterly appalling.

One successful profile picture Rudder shares is a picture of a woman about to bite into (yes) a grilled cheese sandwich.

Women with tattoos, blue hair, big glasses, and funny expressions also make the cut.

Why would this be?

Well, a 2015 study found that men prefer unconventional women. The more independent-minded you are, the better your luck in love.[1]

Someone who’s quirky stands out. You can imagine a man looking at an unusual woman and thinking, “I LIKE this girl! She’s got guts. Not every guy can appreciate her like I can, so I’ll bet she’ll write back if I message her.”

Which brings us to the next question…

What should you write in your first message to someone, if you really want them to reply?

First of all, it should be short. The ideal first message is 40 to 60 characters long. Yes, that’s characters, not words. (A lot shorter than the average tweet!)

You shouldn’t blame yourself if he doesn’t reply, either. You can expect to hear back between 15 to 20% of the time. Which means you should be sending out a LOT of messages if you want results.

But sending out a lot of messages takes time. If you write a customized first message to every guy, it should take you about 2 minutes per message, Rudder says. Any longer, and you’re just spinning your wheels; your message isn’t getting any better.

Given the effort of thinking up something new to say, many guys resort to cutting and pasting the same block of text every time. They can message a lot more women with much less effort.

Is that lame? Or does it really work?

According to Rudder, it’s the strategy he would recommend. A template is 75% as effective as a custom message but takes a fraction of the time, meaning you get a lot better results overall.

Think of it this way. You put in the effort to write a good first message to 6 men, and only 1 of them replies back to you. That can feel discouraging.

But what if you put some time into writing a short blurb that will hopefully captivate the kind of guy you’re looking for, and you send it out to 30 men? Even though your message is not as effective, 4 guys should reply to you.

Those numbers are just guesses, of course, but they give you a good idea of what it takes to get results online.

If you haven’t updated your online profile recently, why not test out these tips? Upload your most quirky selfie and contact a bunch of guys using the same blurb. Let us know if you got results—or didn’t—in the comments!


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