What If You Gamified Your Search for Love?

Tim Denning

That’s exactly what I did in 2017.


Photo via unsplash

Your search for love can look totally different when you treat it like a game.

In 2017, I faced the battle of my life. I entered the world again as a single man after being in back-to-back relationships for most of my adult life. The thought of being single scared me.

I felt I wasn’t pretty enough.
I felt I wasn’t rich enough.
I felt I wasn’t successful enough.
I felt I wasn’t romantic enough.
I felt I wasn’t funny enough.
I felt like a bum for not owning a home (The American Dream).
I felt I was too skinny for any woman to love.

One day I showed up to work and poured my heart out to a woman I barely knew who was much older than me. She laughed at my romantic problems.

What she didn’t know was the woman who broke my heart and left it shattered on the floor in a million pieces was someone she knew well. It was a woman who she managed at work for many years and spoke to daily.

She kept telling me how the two of us would be perfect for each other without knowing we’d already been secretly dating and broke up.


Her approach was to think of dating like a game.

There was a game she introduced to me that had its own app: Tinder.

I was scared to download the game because I felt it was taboo. What if friends, family, co-workers, or people I knew saw me on a dating app? That would make me look desperate, wouldn’t it?

Turns out it was all in my head. What changed my mind was my colleague’s blatant disregard for privacy.

She said to me, “I’m a forty-something-year-old overweight woman who smokes and is a borderline alcoholic. Take a look at all the guys who think I’m good-looking and want to be in a relationship with me.”

Her confidence was rubbing off on me. She simply didn’t let so-called disadvantages stop her from dating. She joked about bumping into co-workers who saw her on Tinder and even dared to tell her. She opened her Tinder app to show me what was possible.

I could hardly believe my eyes. Men half her age that looked like models and had six-pack abs were lining up to go on a date with her. Things became more and more odd as she discussed her sexual adventures in all the raw detail. It was a cross between a Jerry Seinfeld stand-up comedy performance that made you laugh your ass off and a softcore erotica story. There was no detail she was afraid to leave out.

After I got home from work that night I downloaded Tinder. She had me inspired. As the weeks went on she kept sharing her dating stories with me. I pretended I was too heartbroken to download her game and play it. The truth was I was playing the game every chance I got and using what she taught me.

Imagine Dating like Playing Mario on Nintendo

There is your Princess Peach or Prince Charming waiting at the end of the game for you. What stands in your way is many small enemies such as Piranhas, Boos and Goombas. These little obstacles are not the main enemy.

The real enemy is the boss at the end of every level of your dating game known as “Bowser.”

You are Mario, and Bowser is the voice inside your head that tries to hijack every date you go on and tell you you’re not good enough, or you don’t deserve to be loved, or your heart will always be broken.

You win the dating game when you defeat this inner boss at the end of every level. On every dating adventure, there are gold coins you can collect in the form of compliments, confidence and learning about how to love again. These gold coins add to your self-worth.

This Mario world that is dating is played on a dating app like Tinder. You sign up for the app, create a profile and start swiping. The key is to swipe with less judgment. The more you judge a potential person you can have a conversation with and go on a date with, the longer the game will take.

When you play this game you won’t know how you’re progressing. Your swiping actions will seem meaningless. You’ll feel like you’re swiping your life away and getting nowhere. The key is to have faith in yourself and believe you will find love.

The game starts out with a match

Seeing your first match on a dating app is an incredible feeling that will quickly fade. You’ll realize that a match means nothing. As fast as you can match with someone, you can be ghosted.

Being ghosted before you even say a word will be common.

It’s important to understand that in the game of dating, there are problems:

  • There are too many options.
  • People often don’t treat each other nicely on dating apps.
  • There are two ways to use a dating app: to find sex or to find love. Many of the people you’re matching with won’t know which way you’re playing the game, so they may assume you’re just looking for a one night stand. Or they may assume you’re pretending to look for love when actually all you want is some action.
  • There are a lot of fake profiles on dating apps.
  • A dating app can be a huge drain on your time.

I found that the key to playing the dating game is to not make assumptions or jump to conclusions. There will always be people playing a different dating game to you. Let them.

Upgrade to the premium version of the game

I approached dating like a nerd would. I started to study the dating app algorithms. You know what I quickly learned?

Dating apps are like slot machines at the casino. The more money you put into the dating app, the more your profile is shown, and the more chances you have at getting lucky and finding love. I upgraded my dating apps to the premium versions. I also used the paid bonuses many of them offered (like Superlikes) to increase the number of matches.

Try the shortcut to the game

I initially tried to start conversations with anyone who matched with me on the dating app. This proved a useless strategy. Getting a response was hard. Maybe it’s because I don’t look like Dwayne Johnson.

Rather than sit at home alone trying to measure dating profile attributes with my own, I just got out there. Opposites attract. The dating profile doesn’t matter that much, so don’t overthink the dating game.

I found another pathway in the dating game. All I did was send a first message that asked to have coffee in a public place. By cutting to the chase, women looking for love seemed to notice I wasn’t messing around.

I quickly went from zero dates to three dates a day. It was exhausting to go on so many dates.

Treat the date like a game

I approached each date like a game.

Stage 1: Prepare for the game

I took some time to get ready. Wore my best shirt. Ironed that shirt (twice, to get out all the creases). Sprayed one squirt of my favorite Calvin Klein aftershave. Shined my dress shoes. Freshened my breath. Pre-prepared 3–4 stories that would act as conversation starters. Looked over any notes or intel I had on the other player.

Not choosing to look your best is quietly disrespecting the other person.

Stage 2: Play the game the best you can

I was all over the place on the first few dates. I was nervous, scared and annoyed at myself for being a thirty-something-year-old who was still looking for love, while most of my other friends had already got married.

I’d show up thirty minutes early to every date. I’d assess the map I’d be playing the game in. Where are the bathrooms? Where are the potential cafes for later? Where are the wine bars if that’s appropriate? Where is the best place to park my car?

The goal was to be like a tour guide who could show a woman around the level we were playing the dating game in. It made the anxiety ease. My only goal was to get to the end of each date. I’d never listened to my hormones either, that would sometimes get lost in a woman’s good looks.

At the end of the date, I would walk her to whatever transportation she had selected and immediately, subtly, ask about a potential second date. This qualifying question was key to my dating game. Ghosting, I learned, was all too common. Never knowing the outcome of a date was something I wasn’t willing to allow if I could avoid it.

After the date was over I’d remind myself I did my best. It’s easy to be hard on yourself. This a hard game; it’s the game of life.

Track your dating achievements:

  • Did you like them? Did they like you?
  • Did your confidence grow slightly?
  • Can you see yourself finding love even if they’re not the one?

Take a no sex approach to the game

Sex can mess up your thoughts about the dating game. I made sure to put sex in the distant future so I could focus on looking for love, not being distracted by the temptation of sex.

Remove your biases and keep playing the game

The game of dating can be ruined by your biases. As you progress through the game, you may find your biases start to come through. I started doing dumb stuff like going “Well, she’s got a dog, that’s a deal-breaker.”

A friend said to me, “You’d be surprised how good-looking you become when you remove all the filters from the game.”

By filters, she meant all the boxes I was ticking about the person I was searching for. The worst box I ticked was age. I thought that only women who were a similar age to me would consider me an option.

When I blew the dating game up and turned off the filters, everything changed. Women I thought were too smart for me or too good-looking for me started to say yes to going on first, second, and even third dates.

Biases ruin the dating game. Because you have no idea who you’re looking for until you meet the person.

Take a long, hard look at yourself

As you play the dating game you’ll learn a lot about yourself. I learned I was far too in love with myself for another woman to ever love me.

I had to dial the ego right down. I had to listen more than I spoke. I had to stop being so impressed with my own achievements.

Seeing yourself in the mirror after a few dates and a lot of negative feedback can make you feel ugly. The good news is you can change yourself and how you act, so you can magically become better looking in the dating game.

Go to level two with an appropriate player

As you work on yourself, your success in the dating game improves. Each player in the dating game has various levels. Date one equals level one. Date two equals level two . . . and so on.

My goal became to progress each player of the dating game through the various levels. The further I got in the dating game with one player, the more I could let my heart guide me to the right player. Intuition plays a huge part in the game.

There are no obvious signs, only what you feel or don’t for another human.

Put the effort into the game

The thing about the dating game is you actually have to try. You can’t cruise through the game and expect to magically win.

Dating takes effort.

You have to lose yourself in the process and believe in the process. I put a lot of effort into the dating game. It takes an emotional toll after a while. Sometimes you need a break from the game so you can reboot your human software and play the game differently.

You get out what you put into the dating game.

There are other single players, playing alongside you

The whole way through the dating game and through the trial and error of many different dating game apps, I was surrounded by other players.

There were my single friends who were playing the dating game. It was helpful to talk to them about their dating experience and help them in their journey. We did group dates and helped be each others’ wingman/wingwoman.

Dating can be lonely. Being around other single people just like you can make the process a little easier. Just don’t get lost in the story of why you haven’t found the right person yet, or blame the game.

Dare to track the game using a spreadsheet

This might sound crazy: I played the dating game with a spreadsheet.

The spreadsheet was like a CRM used to manage a company’s sales team. I would track each player of the game. How many dates had we been on? Where could we go for the next date? What did they do for a living? What was there favorite place?

I used a spreadsheet to play the dating game because I have a lousy memory. I learned you can never pay too much attention to the finer details of a person. It shows you care.

Play the game over and over

You rarely win the dating game the first time you play. You play the game over and over until you find someone that makes you not want to play the game anymore. Then you both agree to delete the dating apps off your phone and be together, and perhaps live happily ever after.

End the game

The biggest problem with the dating game is you can never choose a player. You can keep falling into the game’s trap that there is always a better option. At some point, I learned, you gotta end the game. There is no perfect player you will discover by playing the dating game.

All the players are imperfect — most of all, you.

Find the person who makes you want to get out of the dating game and work on yourself so you can be with them. Find the person you’re prepared to grow with, as opposed to the person you expect to be a finished product.


Okay, maybe my approach to dating is weird. But I hope it at least gives you some ideas and inspiration for your own journey. You learn a lot about yourself when you play the dating game and that’s the most important part.

When you become self-aware, you see your faults and stop trying to place bandaids over the top of them.

Ready player one? Play the dating game and discover the power of love. Love will change how you see the world, even if you end up single again.

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Aussie Blogger with 100M+ views — Writer for CNBC & Business Insider. Inspiring the world through Personal Development and Entrepreneurship www.timdenning.com


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