Who Switched the Dating-Game from ‘Life’ to ‘Monopoly’?

Samuel Carlton
6 min readOct 19, 2018
He hasn’t shown up yet. He’s still waiting to cross ‘Boardwalk.’

The ‘Scrabble’ of Our Discontent.

“Dating is a battleground filled with deception and infidelity.” — Andrew S. Trees, college-instructor and writer.

I can’t tell if finding a mate is harder than it used to be or not.

I mean harder than it normally is, of course.

The path for lasting happiness used to appear simple: you grew up, went through government-mandated-schooling, maybe went to college or a trade-school, found a job, and started the transition as a young-adult to full-fledged adult. During these time periods, you hopefully found people compatible enough to form a bond called love.

You wanted to be around them all the time. Maybe you eventually started a family or maybe you were content being with each other. In any case, you at least found someone who could consider you their would-be-lover.

You don’t need to do a scientific study to figure out things have changed.

Navigating life’s romantic relationships appears to be easier than ever. Multiple apps and dating websites — Tinder, Bumble, Match.com, pof.com (Plenty of Fish), eHarmony.com to name a few — offer the idea that true-love is only a few clicks away. Just post some pictures, make a profile, wait a few days, and you could have multiple people begging you to take them out on a date.

Add in social media and you can see who among your friends and coworkers are eligible based on their ‘relationship-status’. The wonders of the internet allow for a quick rundown before you even reach the casual-coffee-date or dinner-and-a-movie-extravaganza. The possibilities of endless love at your fingertips await!

So if all of this is true, why does it feel so much harder to find a connection using these methods?

Who switched the dating game from ‘Life’ to ‘Monopoly’?

‘Apples to (Oranges).’

“Your chances of dying a violent death are 1/500th of what they used to be during medieval times.” — Peter Diamandis, engineer and entrepreneur.

It’s not just a case of changing social mores.

Not only are younger generations getting married later, they’re also cohabitating a lot more than previous generations. While numerous articles and sociological tracts will trace this to growing irreligiosity not just in the United States but worldwide, traditional milestones like graduating college and marriage getting pushed later, and even cases of getting ahead in the working world instead of the romantic world — all of these reasons are enough to stir the traditional meet-and-greet out of the melting pot.

While cultural scholars and sociologists may point to numerous causes, many young-to-middle-aged people are noticing how complicated the dating world has gotten in comparison to the past.

For instance, take the following example.

The year is 893. You are a peasant in medieval-Europe. You settle down and get married once you reach the age of 20. You and your spouse start pumping out kids as fast as you can. You end up having six. Three of them die to disease and one of them gets killed after bandits storm your village (32 other people died but that’s just how things go in this day and age). Two of your children end up surviving. After you and your spouse hit around forty, you consider yourself lucky to make it past four decades. You die of tetanus at the age of forty-two. Your spouse dies of grief. Congratulations, that was your life.

The previous paragraph was mentioned almost-not-entirely-tongue-in-cheek. Previous centuries almost required people to get married early on. If you were part of the nobility, marriages were usually positioned as strategic alliances. If you were in the peasantry, marriage was seen as an ordinance of both God(s) and man. Biological urges could be satisfied and family trees could be extended.

If the family as a holistic institution was necessary for childbirth — and if premarital relations were considered blasphemous or problematic — then many people ended up married regardless if they wanted to or not. With threats of disease, natural disasters, war, and famine always present, having many kids was recommended if you wanted to increase the odds of gene survival.

Class ‘(Chutes) and Ladders’.

“My most brilliant achievement was my ability to persuade my wife to marry me.” — Winston Churchill, Prime Minister of Great Britain (1940–1945, 1951–1955).

Fast-forward to today.

In most developed countries considered ‘first-world’, access to advanced medicine, clean water, and fresh food is available in far greater supply than it was in the year 893 (wherever people were). The peasantry has been replaced with a working-class that is able to enjoy higher levels of freedom compared to centuries-old-regimes — even if daily financial-struggle is still part of the game. Even middle-classes and higher-classes in many countries are not necessarily bound by the old rules of alliance, kingship, and arranged marriages.

Add in the 60’s — 70’s sexual-liberation, and global reconstruction after World War II, and you have many ‘old rules’ and ‘laws’ for dating and courtship which simply don’t apply on an international scale — at least, not like they used to.

While those who still practice the conservative-variant of marriage in their home countries will practice courtship in traditional manners, a younger and more secular generation is choosing to use the modern tools at their disposal. With online-dating, bars for every sexual-orientation and interest across the spectrum, activity-oriented-meetups, and niche-conventions being a dime-a-dozen, the chances of finding compatibility can go as far as you’re willing to look.

Which is why some are realizing that using modern services can make the process more exhausting than it already is.

If a first date is this romantic, pretty sure it’s all downhill from here.

If dating and marriage were previously tied to how ‘Life’ was ‘supposed to go,’ it can feel like these services almost have a ‘Monopoly’ on romance-seekers everywhere. Instead of going out and meeting people, you don’t even have to leave your house to browse the marketplace. You can merely swipe and click your way through a surface-level-understanding of somebody without even having to meet them.

You think they’re hot and have similar interests? Swipe or send a message. No reply? Well, that’s a shame…but you can move on to somebody else. If these apps and profiles are mostly based on optics — looks, interests, income, etc. — there’s no way to account for personality. On paper, somebody may seem like a perfect fit…until you finally land a date with them and realize they did their master’s thesis on Shakespeare and refuse to speak in anything but iambic pentameter.

Not a good look.

Preparing for the ‘Operation’.

“It seems essential, in relationships and all tasks, that we concentrate only on what is most significant and important.” — Soren Kierkegaard, philosopher.

So what’s the solution?

In a world where certain companies and apps have forayed into the cultural mainstream, the quest to find a significant other can feel like trying to buy properties during a rigged game of ‘Monopoly.’ Certain people may possess a checklist of superficial traits people are looking for — leaving others that don’t out in the cold by comparison. People who don’t possess a body sculpted by Michelangelo — or endless bank accounts — may feel inadequate in the surface-level-online-dating-world compared to those who do.

For those who feel inadequate every time they open an app or use a service, they might be better off doing things the old-fashioned way.

It is still accepted that a ‘minimum standard of attractiveness,’ is important in the overall picture. However, having a charming personality can help close-out a date if the object of your affection may be on the fence about your looks. Because of this, going the traditional route of meeting new people face-to-face may still end up being the best option. No longer do you have to play games involving witty text messages or first-dates turning into non-dates after you realize there’s no real chemistry beyond how they look.

Which is why social settings such as bars, clubs, hobby-shops, conventions, mixers, and others are still great avenues for old-fashioned-courtship. Getting out and having a good time with your friends — or people you don’t know — will still kindle a would-be-romance. Working on your presentation — of appearance, dress, or conversation-starters — gives you room to work in three-dimensions instead of a one-dimensional-profile that just gives the appearance of who you might be.

So even if the Dating Game has evolved from ‘Life’ to ‘Monopoly’ over the years…

…we should give ourselves the freedom to play chess instead of checkers.

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Samuel Carlton

Writer. Blogger. Sales Professional. Film Buff. Coffee Addict. I write about tech, movies, stories, life, current events, and the future.