The 10 People We’ve Probably Dated

By Shayne 


Valentine’s Day is a corporately-puppeteering time of the year where thousands of couples engage in a social media arm’s race over whose relationship is more “cute”, while simultaneously criticizing other couples for being tryhards. 

At least, that’s what I think it is. 

While many people are spending time with someone they mostly just tolerate during the other 364 days of the year, the rest of us are left to bitterly reflect on why we’re spending today by yourselves.  

So I’ve decided that, instead of everyone sulking on their own, it would be a good idea for us all to take a stroll through our dating graveyards and revisit all the people that didn’t pan out. 

Here we go: 



1. Mr/Ms “Bad Timing”

The classic.

You know, this is a person who checked all of your proverbial boxes: they were funny, attractive, frugal (but not cheap), didn’t think that your weird left ear was all that weird, and they even had similar taste in movies.

But then, as fate would have it, you’re hit with a dose of reality:

He/She/Whatever is going to a grad school across the country.


They just accepted a job offer that’ll put them in Singapore for 6 months…at least.


You were actually only in town for a couple weeks due to a work training, and now you have to return to your chill life in Seattle and leave Wisconsin in your dust forever.

Whatever the case is, things end quicker than either of you would prefer, which precludes building a strong enough foundation to even attempt a Long Distance Relationship (henceforth referred to as “LDR”).

So you painstakingly part ways, promise to keep in touch and reunite, and progressively lose contact as you move on to the rest of the people on this list.

What you learn: We humans aren’t the most rational creatures in the multiverse, so we tend to place higher perceived value on things that have a dimension of scarcity to them.

The World Cup wouldn’t be the biggest sporting event of the world if it was played every 6 months, and this person probably wouldn’t have stolen your heart if you two actually lived in the same city.

So don’t beat yourself up over “bad timing”–this person would likely have ended up as a 3rd string player anyway.



2. The Poisonous Person

This is the person who all our friends said was toxic for us.

And we didn’t believe them, because we were stupid.

We were too stupid to realize that the constant fights, invasions of privacy, and mutual lack of trust weren’t all examples of intense love, but rather signs that the relationship would eventually blow up like the fucking Hindenburg and take your capacity to trust another person with it.

I’m not here just to criticize us, though.

I understand the appeal of these people. Few other things in the world inspire such visceral, intense emotion as a toxic person. But that’s only because humans pay WAY more attention to negative emotions than positive ones.

So no, it’s not really a sign of love, but a sign that a deadly combination of lust and distrust will cloud even the most rational person’s judgement.

What you learn: Well for starters, you learn that this type of relationship is ultimately childish and best reserved for recent grads who’ve convinced themselves that they’re real adults.

Second, and more importantly, we learn that toxic relationships are a two-way street. We were probably just as terrible for that other person as they were for us. Hopefully, this inspires some self-reflection on what it actually means to love and be loved.



3. The “Lightning In A Bottle”

You had a great first date with this person.

Maybe even a great second date.

Things seemed to be going well, until….

….well, until nothing, really. You just never saw one another again and things fizzled out.

It might have been because scheduling the third date was tricky.

Or that one of you went out of town long enough for you two to forget about one another.

Or maybe both of you were just waiting for the other person to initiate something else, but neither side budged.

For whatever reason, you both left a lot of potential on the table, and now have just relegated one another to being Instagram friends.

What you learn: Strike while the iron is hot. Or else, one day you’ll check their IG feed and see that they’ve ended up with someone WAY lamer than you.



4. The “Silver Medal” Person

This person is like Mario in Super Smash Bros: well-rounded, can be decently effective in most areas, but isn’t overwhelmingly spectacular at anything.

This person gets B’s and C’s across the board: attractiveness, intelligence, humor, ambition, interests, etc.

And just like Mario, nobody will really fault you for picking this person…but they also won’t praise you either.

Nobody ever says, “Nice, I LOVE Mario!” when you pick him. It’s more of a, “Hm, cool”.

Mario is safe, and you know what you’re getting when you use him.

That said, there’s probably a reason why not many people outside of beginners pick Mario.

As terrible as it sounds, there’s something in us that devalues our partner being “safe”. At least, at this stage of our lives, anyway.

We like Mario, but we don’t love him. We love Fox, Marth, and Captain Falcon. We love characters who have glaring flaws, but also incredible strengths that can make them top-tier in the right situation.

So after a while, we get bored of Mario, and move on to try and make Ganondorf work.

What you learn: Sometimes, being well-rounded and good for everyone means that you’ll never be great for anyone. Mario is great for people who are 40, not for people who are 25.

Go and get yourself a Falco.



5. The Serial Clinger

This person met you, fell in love, and started making wedding arrangements within the same 4-day span.

Which makes you feel pretty good, until you realize that they did that with the last 11 people they dated and will likely do the same with the next 11,000 people.

It’s like watching someone who’s REALLY bad at Sonic the Hedgehog play on fast-forward. They’ll come out strong, make the same stupid decision that they made the last 200 times, only to re-spawn and do it all over again.

As a result, you realize that you’re more of a means to an end than someone who they actually like. You’re just another Sonic stock that will be easily discarded and replaced with another one.

What we learn: If we literally just sidestep this person when they next try to hug us, they’ll just keep walking until they latch onto their next vessel.



6. The “Square Peg”

Despite glaring fundamental differences between you two, you both still tried to make it work .

Whether it was a difference in cultural, religious, political, or family values, you both knew that things would never work out in the long term.

It was an ultimately futile effort, but a cute one.

You tried finding fun things to do together, stayed at each other’s place a bunch, and probably had some great sex.

At the end of the day, though, the writing was on the wall.

One of you will bring up the insurmountable differences, the other will painfully agree, and then you both move on.

What you learn: Dating doesn’t have to necessarily work out long-term for it to still be fun and fulfilling.



7. The Person Who Is Out Of Your League

Remember what it was like to hang out with your cooler older cousin and constantly self-monitor yourself so they would like you?

That’s exactly what dating this person is like.

You were somehow able to get them to at least be interested in you, and now you’re freaking out about keeping their attention.

You start reading WAY too much into their texts, you worry if you call them too frequently, and you spend days agonizing over that time you revealed that you don’t actually like peanut butter that much, seconds before they said it was their favorite food.

You’re basically walking on eggshells that you’ve laid out yourself, because you’re so afraid of pissing them off and having them realize how much better they can do.

The ironic part of this is that it’s your constant insecurity that eventually annoys the fuck out them.

One of the least attractive things anyone can do is be overly insecure. It just so happens that the most desirable people we come across end up making us insecure.

What we learn: This person liked us for who we are, and if we approached the relationship with a confident mindset instead of a pathetically sheepish one, then they probably would have stuck around.



8. The 98%-er

This person gets straight A’s across the board…except for one thing. They actually get an F in that one.

As luck would have it, the thing they get an F in happens to be the one thing you value above all others.

It could be that they’re bad in bed.

Or that they don’t exercise, and never will.

Or, it could be that they don’t drink.

Or that their laugh is too loud.

Or that they’re a TERRIBLE dancer.

Or that they don’t like pina coladas, and getting caught in the rain.

I’m just guessing at these by the way–definitely not speaking from experience. Promise.

Whatever it is, this ONE thing sticks in the back of your mind as you frantically try to justify how much you like this person.

However, the constant attempts to minimize this major blemish only ends up inflating it even more, to the point that you can’t take it anymore and break things off.

They were 98% perfect, but the missing 2% was just too much.

What we learn: That we’re willing to throw away someone who’s likely better than ANYONE we’ll ever meet because their parents are Republican.



9. The Co-Worker

“Nice going, dumbass.”

That’s what I’d tell my younger self if I could, since I once (twice?) dated someone I worked with.

On the surface, dating a coworker sounds pretty cool. You have the same commute, the same general work schedule, and you can complain about your job with the other person knowing exactly who and what you’re talking about.

However, the fact that you’ll likely end your life with more exes than spouses means that your chances of a work relationship panning out are slim.

And you know what happens when they don’t work out?

A whole bunch of bullshit, that’s what.

Suddenly, walking to certain parts of the office becomes really awkward.

Your friend group might get uncomfortable with the breakup and pick sides.

Your overall productivity takes a plunge because all you can think about is how much you hate your ex and how stupid his/her new hair looks, even if it actually looks really good.

You dread going to work, and now you also dread going home, because you’ll be alone there and thus have plenty of time to think of all the new people they’re seeing.

So yeah, way to go champ, you just ruined your job.

What we learn: When it comes to dating someone you work with, measure thrice and cut once.



10. The Basket Case

To paraphrase a quote from one of my favorite movies, Scott Pilgrim Vs. The World: this person’s got some battle scars, dude.

The amount of baggage that weighs down their interactions with you is almost palpable.

It usually comes in the form of dark or self-deprecating humor, random emotional popoffs, or a general sense of aloofness when it comes to your relationship.

They’ll also usually give you bullshit warnings about how you should stop seeing them because they’re afraid they’ll hurt you…a fear which ironically causes them to be emotionally unavailable, which hurts you.

Whenever it seems like you’re making progress, they’ll either act like a huge jerk to push you away, or disappear completely.

Eventually, you get over their immature disdain for affection, and seek greener pastures.

Or you don’t, stick around because they’re (usually) very attractive and good in bed, and eventually get ghosted by them.

Your choice.

What you learn: If you ever encounter one of these people, run.



*Bonus* The Person That Unexpectedly Broke Your Heart

You were all in on this person, told your friends and family about them, and would occasionally fantasize about the life you plan to live with them.

…And then they unceremoniously dumped you and will never talk to you again.

That’s it.

No explanation.

No closure.


What we learn: Jack Daniels doesn’t taste so bad after the 18th shot.



Thanks for reading! 

Seriously, thanks for making it this far.

My main hope is that you leave this article knowing that there’s no shame in failing at dating. Because, at the very least, we can all laugh and commiserate about it together.

Happy Valentine’s Day!


Leave a Reply

Your email address will not be published. Required fields are marked *