Successful pickup artists know that it takes more than luck to get lucky. Like those expert pickup artists, we try to use attention-getting techniques and build strong trust-based relationships with our community.

What Is It All About?

Ace Hotel, New York City — by day its lobby is a bustling coworking space, but come nightfall, it’s an intimate bar with singles looking to mingle. People build startups in the morning and romance in the evening. When it comes down to it, they’re almost the same thing.
A beautiful Italian in red crosses her legs and recounts a recent date: “Everything was good for the first half-hour. Then he moved his plate aside and started in —”
“I work as a VP,” he boasted, “I’ll be an associate in 5 years and I grow tomatoes at my place on 5th Avenue.”
It sounds like the typical story of a boring date, or… a boring landing page. Or newsletter. Or sales call. They all go about the same.
This article is about:

How to Be a Dull Showoff

Why Dates Get Boring

Because everything is cut and dry. Consider the above-mentioned couple: obviously, the man likes the Italian. It’s clear that he wants to impress her. And it’s as clear as day that the woman is in charge of the situation: she can turn him down any time.

Why the Internet Gets Boring

Same story. Let’s compare:

What they mean What they say on a date What they say on the web What everyone hears
We are successful “Let me tell you how I tamed a lion” “We are all Ph.Ds, MBAs, DNAs. And we live in Thailand!” “Blah blah blah”
We are surrounded by successful people “My friend is coming by, he hooked up with Miss Universe the other day” “Our clients: *Paste the logos of all domains from which someone has ever registered on your website* “We almost believe we deserve you, honestly!”
We are fun Embarrassing drinking stories “We’ve got an X-Box, bean bags, and fridges full of organic foods/craft beers/smoothies in our office.” “We’re not as boring as we seem”

On dates, people observe one another and try to score. On the internet, users get segmented and put into a sales funnel. Something has got to give!

How Not to Be a Dull Showoff

Creating Tension

It’s important for both sides to gradually expand their boundaries, and as a result, become closer to each other. You need to keep that gaming element in your relationship. Let’s consider another example:
Noon, Buenos Aires. A guy sees a woman with a huge disobedient dog. He says:
– “Your dog needs to lose 20 lbs or maybe you just need to gain 20 lbs”
– “Perdon?!?-” she asks in surprise.
– “Your dog doesn’t listen to you and leads you around however it wants.”
The woman smiles doubtingly.
– “Do you know how to train dogs?” the man asks playfully. “Let me show you.”
Here’s how we come to an important point. One has to build a comfort zone with the help of:

  • Kindness
  • Interest

Then you can get into a private space, perhaps rarely, and even just for a bit.

How Not to Go Overboard

How Not to Be a Pig on a Date

It’s not easy. Many of us have been there — being rewarded with a snicker, rolled eyes after a bad joke, or even worse, being ignored right on the spot. That could be the subject of a whole separate article, and it would surely be embarrassing to write it.
However, there is something most of these cases have in common: It’s when someone only thinks about one person — themselves. They only talk about themselves or something they know. That doesn’t work. Instead, one should be truly interested in the other person, have empathy, be careful, kind, and curious.

How Not to Be a Pig on the Internet

All the same again — be curious, friendly, and give gifts. Only then may someone be ready to let you into their private space, even for just a moment.

Internet Communications Revisited

Creating a Comfort Zone on the Internet

It’s less about showing off and more about helping the community. We’ve made and probably keep making the following mistakes, and we are ashamed of it, but that doesn’t mean we can’t change our ways.

The wrong way The right way
Decorate your office with ping pong tables Create open source resources and freebies
Abuse competitors Suggest open technologies
Post hot-dog-legs photos: “I’m working in heaven” Post screenshots from Jira
Canned support responses: “Your opinion is very important to us” = it won’t change anything “We’re planning to do it this way or the other way — what do you think?”
Show off your capital Openly speak about how you spend your money

Icons8: From Self-Interest to Community

When we created Icons8 we saw it as a maketing hack. Instead of buying links for promotion we simply put our icons online as a free download and asked users to post a link back in exchange.
People gave us more than credit. They also sent us words of gratitude and love in the comments (we didn’t switch comments off in WordPress because we didn’t know how). And they actually used the word love.
It turned out that a business’s self-interest can evolve into a great community, which became part of our principles. Together we specify our project’s direction, generate content, and communicate with our users using lots of warm, lively, and sincere words.
In other words, there is a wide comfort zone. Just like with a date, it’s good to create some tension.

Creating Tension on the Internet

Method 1. Turn the Tables

Instead of desperately following users with various selling and marketing texts, try positioning yourself as an object of desire. Here are three examples from our newsletter introductions:
We’re afraid you’d think we’re easy, so we haven’t written since December. But we can’t keep silent: here’s a free Windows 10 icon pack.
We’re not that psycho ex of yours, we won’t get drunk and send 18 messages. In fact, we haven’t sent anything since 2014. But now we’ve got a good reason: The Ultimate Toolkit for Responsive Icons.
We thought you might be feeling lonely over there so we decided to drop you a message and give you some attention.

Method 2. Don’t Get Pregnant

There is a good old-fashioned way professors use to attract student’s attention during lectures. They suddenly say the phrase: don’t get pregnant.
Many other subjects can strike the eye. Here’s one way we do it:
This page is constantly screenshotted, tweeted, and praised. A user stops for a second during the usability testing, giggles and says: “Ha — you’ve got my attention!”

Method 3. Tim Cook Eats Penguins

We made up a few absurd headings designed to resemble tabloid news. Users see them after they have downloaded our icons for free. That’s how we remind and ask people to set a link to Icons8 (see the yellow strip):
Tim Cook Eats Penguins
A few more variations:
Getting User's Attention
It’s important to laught with a client, not at a client. In this case we succeeded. In others we didn’t.

Method 4. Smile At the End

Articles are complicated. When someone opens our message we only have a couple of seconds before the user decides if they should keep reading or not.
According to the inverted pyramid method we have a chance to diffuse the tension only in the last point. Our editor Josh likes to finish lists like this:
Smile At the End
As a comparison, see quite long humorous texts on another page. We enjoy them a lot, but sadly nobody reads them:
Humorous Texts

Method 5. Good Boy License

You can also call users names.
For instance, we call our clients mama’s boys and they seem to like it. We released an icon set under the Good Boy License.
Meanwhile, our serious clients demanded we added an MIT Standard License. See how tension can work both ways once the trust is there?


We can learn a lot from the principles of successful pickup artists:

  • creating a comfort zone for users
  • one that is established, they may just let you get into their private space

The big test is, do people actually like it? They love it, and they make no bones about expressing their feelings:

That doesn’t mean that we don’t still get into difficult situations:
Negative Comment

So What Do We Say to the Italian in the Hot Red Dress?

Many interesting things, for example:

  • “Stop staring at my breasts, I’m not an easy man”
  • “I’m looking for someone who sees my beautiful soul, not just my perfect body”
  • “Luxury cars aren’t comfortable. I’m looking for someone who drives a hot dog cart”

You can say it to your users as well. But one thing at a time, ok? 🙂

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