Making Connections: 12 Things Online Dating Can Teach Biz About Connecting on the Web

When it comes to doing business on the web, one need look no further than the world of Online dating to glean a little insight and direction. In this post we’ll explore 12 things the singles scene on the web can teach business about creating high quality connections.

 1. We compromise ourselves (values, virtues, stories) based on the image.

A tantalizing prospect can get you to change your whole personality or brand. It doesn’t take more than a great photo and short story to get us to read into it. A pretty face, a big budget, a few clever words and details and we find ourselves fumbling on our own positions. In fact many tend to flake and cave on their values, ethics and morals.

The integrity of a brand is often compromised in the face of a good deal. Loyal partners and customers are betrayed in the face of a cheap and temporary gain. Companies and relationships rise and fall like this all the time.

Perhaps what is worse is the illusion that tricks/tempts us all to compromise our values. There is a natural bias to trust a pretty face. (So use it if you got it, but use it for good). Most online interactions are poor substitutes for genuine experience. The prospect’s profile, site, and portfolio isn’t the reality. Yet many take what little they can trust and project their own desires and draw many conclusions from innocuous details and a fancy facade.

On the business side – this should convince you to create a more attractive image. Get your shit together. Tuck in your shirt. Brush your hair. Also, be mindful that integrity and reputation multiply your earning potential. So don’t compromise your values, quality, or integrity or deal.

2. Obsessing over a single, idyllic mold of a prospect is an easy way to fail.

Whether it’s set for perfect mate or customer, we rarely if ever fit the mold. Why in business or life for that matter do we attempt to obsess and pursue an imaginary, perfect target?

In the business world there is plenty of useless marketing research based on the notion of “perfect” customers. And on the world wide web, this becomes interactive fan fiction. We want to believe they exist and spend much of our time, effort and energy pursuing it. We build entire business models on it. What fraction of a percent of your market fit that ideal target? If 99% of your energy is spent chasing less than 1% of who is out there, are you getting a large enough return? Or is the return still in the imagined future? Be careful Ahab, chasing white whales can cost you.

Let’s be real for a moment. We’re not really looking for perfect. In fact there are many characteristics and qualifiers we’re willing to throw out for the right individuals. There are essential qualifiers, a mix of nice to haves and a reconciliation of red flags or potential deal breakers. The acceptable mix varies from person to person. We can even map these out, count them and calculate our share of the market and the available opportunity. These are worthy strategic endeavors. Consider expanding the size of your target. It will increase the likelihood that you’ll hit it.

Operating on the idyllic expectations causes faulty thinking to sneak into our strategies and behaviors that result in a lot of wasted effort, energy and resources. We’re often all to eager to chase the unrealistic. In business, we operate on quantitative, often linear metrics that come to an apex of a perfect target and assume it/he/she exists. Is this really more accurate and relevant to our efforts or is it simply easier to think of it this way than dealing with the murkiness of qualitative approaches? Our we focusing on a target or missing realistic opportunities. As Musashi teaches many in business school – it’s vital to reconcile narrow and broad thinking.

Am I saying you should stop dreaming? No. Not at all, but let’s agree that there is plenty of data/experience that shows we could be more discerning and aware of our assumptions, efforts, projections and missed opportuntities.Furthermore, we’re rarely if ever perfect prospects or consumers.

When was the last time you remember sitting, waiting with a pile of money under your pillow dreaming of your pain points and descriptors of the perfect solution to rescue you from your problems? We rarely focus our complete/perfect attention on any of our problems at any given time. Why do we market to prospects as if they do? When you start thinking about people as if they are human beings -scatter brained and distracted, you can begin to think of adjacent concerns and opportunities to engage them. You can also more accurately qualify them.

Imagining your ideal prospect is like this

The expectations we set based on ideals often allows us to dismiss good candidates for the dream of better- or -fucking magical in this case. I’m not advising anyone to settle for mediocre, but rather focus more attention and awareness to the wisdom of their experience and an adaptive attitude of acceptance and comprehensive understanding. I know- it’s harder, less math, more heart, more conversations, harder to systemize. Cry me a river.

3. Making huge projections from weak signals causes unneeded heartache. Being Steadfast by qualifying your prospects can save you from a world of grief.



We are so desperate for data (validation) these days that we project on the weakest data points and often mapped in a perfect line to our desired outcome. It leads to thinking and assumptions that small behaviors amount to extreme approval/ evangelism. A prospect winks at you, or likes your page, and marketers (your BFF’s) go bananas; as if it means that they are focusing all their time/attention on you.

Observation: Someone winked at you.
Steadfast Conclusion: Possible interest – qualify them.
Crazy Talk: You think they love you.
50 Shades of Reality:
They winked at 40 others and waiting for first/best reply.
They’re bored at work (as a mall security guard or something hilariously upsetting).
Their spouse isn’t giving them the attention they desire (sad but truly happens)
They’re interested if and only if no one more attractive/interesting responds first (Mr./Ms. Right Now Syndrome)

The Information Age affords everyone the opportunity to take the shotgun approach to shopping. In the online world, people cast a wide net, play many games, and behave differently for many reasons. Your job is really to quickly disqualify the riffraff and qualify the true prospects.

This is a huge challenge and begs a few questions such as:

How should we think about Mr. & Ms. Right? How do we qualify them?

Well strap on your Chief Executive Customer hard hat and let’s examine this for a minute. In the dating world and business world, it’s often the goal to create a volley of questions. Showing genuine interest and concern for your prospect as well as your own brand is important to building the appropriate level of intrigue. Getting a prospect to ask a question is a great opportunity to provide an experience, some insight into who you are and how you do things (commercial teaching). Desperate people and bad salesmen will talk about themselves too much in ways that seek validation vs. entertain/inform the prospect. They will also completely disregard their concern for their own brand/organization and ask questions to pander and qualify. This exudes weakness/desperation. Conversation is of course an art, but in general, in business and life, we enjoy interacting with people who are comfortable in their own skin, concerned for it, and willing to collaborate to create a fun experience.

4. Insecure brands and people pretend to like everything their prospects do.

Can we all admit to fudging our identities and values a time or two? Sometimes we don’t know how to communicate the truth in an authentic way that mitigates risks. Sometimes we’re just scared. We haven’t honed our message or story down in a way that doesn’t make us sound crazy. I know I’ve been there. So in the face of fear, we mirror our target or go to something generic. You like long walks on the beach? Me too! I love Star Wars/ Twilight / Hunger Games! Be honest- If you had a shot at which ever half of Bran-Jolina you prefer, would you mirror their interests or be yourself?

At a strategic level, brands take an all-positive attitude towards everything. In fact many organizations, platforms and brands have all but made it a crime to dislike anything. I find fault with that. I don’t trust brands/people that believe they like everything. They strike me as those who are either dishonest or who don’t know themselves or reconciled all their parts; good, bad and ugly. To steal from Hemingway, people have an exponentially growing resilience to bullshit; their shock proof shit detectors are set to level 11 these days. So do you want to come off as insecure and dishonest or confident and genuine? Where’s the bigger market opportunity? Be mindful when you’re mirroring others.

5. It’s all too easy, tempting addicting to pretend Online.

Here’s a rarely expressed notion – photos, videos and other imagery on and off the screen are abstractions. Interactions on the screens are abstractions. It’s hard for our brains to take people seriously online. It’s easy to apply a self-centered mentality on the digital domain. The same mindset that allows you conquer a video game (whether you’re launching birds at green pigs or running over pedestrians in Grand Theft Auto) allows you to selfishly progress through a singles dating site. You literally game the system and inevitably start pretending. This may manifest into something as innocent as feigning casual interest to copying and pasting messages to multiple recipients. You may think to yourself- well I don’t do that- these are real human beings I’m interacting with, but study after study reveals a different story. It takes a lot of brain power to emote with people on the screen in the exact same way we would in person. On the screen, we’re more likely to be dishonest where it serves us and act more selfishly.

6. It never lasts when you fake it.

Faking interests/aspects of your persona to force a false connection requires extra energy and in business and life. Eventually your reserves are depleted and your true identity comes to light. The short term result is usually conflict and loss. The disingenuous connections while largely in the majority do not last. In the long term, you burn your way through a market and a reputation eventually spreads. Troubled and disingenuous brands tend to treat customers like disposable resources. When the jig is up they move on. It gets expensive and tiresome after a while. The cyclical existence of short flings are not good for the health of a brand. People respect a good brand that’s willing to settle down and grow its customer base in a long term committed relationship.

7. Short flings are exciting distractions that help us procrastinate our own development.

Small business knows this all too well. This is one of the many things that keep them from growing; investing only in the short term what you can have now (small deals), vs. making longer, more strategic plays that could help you grow. There is a never ending supply of squirrels to distract us from our true goals. These distractions enable us to put-off the serious thought, reflection and strategy to improving our situation.

Taking the time resolve issues and course correct can have a profound impact on the results.

Personally, this may mean resolving your issues, healing old wounds. Professionally this may mean identifying opportunities to optimize processes, organize efforts, and take time to think strategically. This sounds incredibly basic but when’s the last time you had a strategic session with yourself let alone the rest of your team?

8. Common ground is qualitative and requires matching depth and/or intensity.

When you say you like Twilight – how much do you mean? Will we have to watch it every weekend or can it be any time I’m out of town? Is it like dessert and to be taken after dinner each night? This isn’t a yes or no question but it has serious implications towards how well you can connect with your prospect. In the business world. There is a lot of yes or no questions being fielded when it comes to shared values, and few qualitative measurements. Many businesses (Fortune 100’s) believe they’ll come off as more connective when they say that they have something in common without having to go into detail.

9. A Checklist Mentality towards shared interests does not make for good matchmaking.

In the early days of Online dating- matching interests was done via a linear yes or no questionnaire. This lead to matches based on really poor evidence of shared interests. Robbed of context and depth, it’s really difficult to qualify just how well you’ll resonate with another person or group. The checklist mentality is still running strong in business today

Do you have a website for your brand?
Is your website customer-centric?
Do you know your brand values?
Do you enjoy long walks on the beach?

And while it’s gotten a little better, it is still built on a system that is too easy to BS through. When it comes to connecting a brand to prospective customers, the mechanism is the same. Both parties tend to respond in a way that they perceive is favorable by the other despite their true positions. We’ve evolved to another linear model when attempting to measure quantify the qualitative- the “strongly disagree” to “strongly agree” scale is the latest exercise in hilarity.

(Alright statistics fans, warm up your emails and let loose the hate mail). Balancing the sacrifice of depth with our expectation of instant feedback leans in the favor of poor results. Using these results to derive greater conclusions and match any group together will prove to miss the mark to an even larger degree.

10. Those confident in their identity, are always in high demand.

In the Information Age, there are a zillion images to make you feel insecure, and unsure of your own identity. There is a global market full of direct and indirect competition who are doing many things better than you. If you define your identity (brand, personal or professional) only in comparison to others, you’re more likely to make many of these mistakes. If you first know thy self and thy brand, then reconcile with others, you’re more likely to be resilient, confident and desired. Your actions and strategies will reflect these positions. Prospects will see it.

“Nosce te ipsum”

“You know what that means? It’s Latin. Means Know thyself. I’m going to let you in on a little secret. Being the One is just like being in love. No one can tell you you’re in love, you just know it. Through and through. Balls to bones.” -The Oracle in The Matrix

Those who don’t give into the opinion of the multitude are usually seen as leaders, contrarians, creatives, and so on. While not always positive, they are differentiated and distinguishable from the crowds and “meh” opinions. Confidence is a key trait.

11. A discerning identity is one that people are more likely to trust and respect.

Making a discerning opinion known is risky and yet has the benefit of allowing you to stand out for what you believe in, where exactly, you draw the line, and your reasoning behind that distinction. Standing out from the crowd lands you a job, gets you the prom queen/king, and always involves risk. It can also get you fired, arrested, secluded, outcast, and so on. So it also comes down to subtle distinctions, nuances and details.

This is not the same as running to a contrarian extreme in excess in hopes of being labeled a rebel or rock star.

“Excess ain’t rebellion. You’re just buyin’ what they’re sellin’.” Cake “Rock N Roll Lifestyle”

Subtlety when wielded appropriately, reveals compassion in a death blow, mindfulness, discipline, and compassion; mastery of craft with a respect for life. Many if not most people and brands have yet to do the work to dig to their cores to notice the subtleties that truly make them great, distinct, and wonderful. These unexplored nuanced truths make for the most compelling, connective and engaging stories. And when you dig in and dare to tell the true story, with blossoms of nuance, often you’ll find that the true stories are far more compelling than the BS you think you need to sell.

Now, if you’re a professional procrastinator, you’ve lead your life and career attempting to skimp your way to maximum effect. The reality and result of this attitude is that you’re doing what most do, and not creating or meeting a market need. Is there a short supply of Average Joess and Janes? How about empty headed, image obsessed gym rats? Nope. Don’t commodotize yourself. Emphasize the complexity and nuance of your brand.

12. Old News-Most of the time, the best place to catch them is not Online. Real-life experiences tend to give us better information and stronger impressions.


For many businesses and every person, the web is a means to an end. Yet there are many souls and brands who are completely lost and stuck on the web obsessing over interactions that aren’t converting. You might be upset, enraged with “I want to believe” sickness. You want to believe you can build deep connections on the web. You can, but  they’re relative. Compared to what you can do in real life, accept no substitutes. Study after study (and experience) has shown that are friends are not really those who we can count on a screen. They’re the ones who pull us out of holes, bail us out of our worst moments, and laugh with us at every misadventure. And why many may want to believe that we’re closely connected and engaged with the umpteen hundred thousand people we can reach on the web, what really reaches most of those removed from your immediate circles, is a faint buzz and static.

Used appropriately, the web connection can land you the first date. That’s the plan remember? The whole  point is to use it to connect face to face. Finding shared values & experiences are great ways break the ice, lure a prospect, and attract an audience to a cup of coffee. Practicing your values, doing what you love to nth degree , sharing your stories, and being open to those that you meet in real life will organically lure the appropriate people.  Being a good storyteller with your real life can earn you quite a bit of attention.

Those moments are also where you’ll really need to bring your A game. The face to face meeting is where we get better signals for levels of interest and integrity. At Heroik, we refer to the first meeting as a cup of clarity. We’re scrutinous about qualifying our prospects while providing value up front. We watch, listen, interact and follow up.

Final Thoughts – Positive Indicators vs. Conversion Points

None of this means that you shouldn’t strategically peacock and strut your stuff on the web. Shaking your tailfeathers and attracting others to your assets are all part of courting process. You swim in the right circles and some markets adjacent to your interests, open to opportunity and it will find you. Be mindful to your offline experience and true conversion points.

The number of cups of coffee you bought might excite you but  is not yet a measure of success. It’s another positive indicator not the conversion point. When you’ve made a mutual commitment and contract, collaborated on a few endeavors, then you can count your chickens.






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