Original: The Ill-Matched Couple by Lucas Cranach the Elder

I recently celebrated(?) my 60th date. If you know me, or you’ve dated me, you probably know that I have an Excel spreadsheet where I track every first date I’ve had since moving to Canada, in January 2022. Controversial? I don’t know. A red flag? Maybe? In any case, it helps me, a guy with bad memory, keep track—and tabs!—on all the lovely (at a time) potential forever-afters. If anything, it makes for a great tool in case you get chancre, and you suddenly see yourself in the awkward position of tracking down the possible culprits. Not that this ever happened to me, of course. 

So anyways, yes—I’ve dated 60 people since January 2022. Now, I say “dated” semi-loosely, since I also add random, casual one-night-stands (more like 45-minutes-stands—AYOO!). I haven’t “romantically” dated 60 people. Who has the time? Who has the emotional bandwidth? That shit only happens in 90s sitcoms. 

The dataset is as follows:

Name

Age

Gender identity

Nationality

How did we meet (apps, through people, irl)

Did we have a date? (Y/N)

How many?

Did we have sex? (Y/N)

How many times?

Notes

Now this last column is the most recent addition. I included it after I couldn’t remember a specific person I dated back in summer 2024 (more on that later). And, even though the rest of my sheet is pretty serious, pretty unbiased, pretty quantitative, this last column is where we can have a little fun, where we can get a little crazy and let our hair down a bit. In it, you can find some wholesome gems such as “We kissed outside a bar” or “Said ‘I think I love you’ after sex”; or deeper, insightful ones like “Worked in the movie ‘Backrooms’,” “Surprised spat in my mouth,” and “Witch”. 

Point is: I’ve been at it and it’s been a winding road. In my efforts towards finding a legally Canadian partner the love of my life, I’ve had many experiences which, regardless of their quality and outcome, have collectively helped me get a few takeaways in regards to dating / trying to find love in your 30s. 

Today, I selflessly open the vault and reveal some of what I’ve learned throughout this daunting, fun, and at times WET endeavour. Everyone’s been asking me and you are so very welcome. I do gotta say that I’m most definitely NOT breaking any ground on people-in-their-30s psychology. These takeaways are of the “Duh! Obviously!” kind, and arguably surface-level, but you’d be surprised on how many technically adults seem to have missed the memo on them. I’m certain. I have the data to back it up, as previously mentioned. 

Anyway, here are some of my biggest thoughts/takeaways/lessons:

You can’t control people, only influence. 

Ok—relax, I don’t mean “influence” in the insidious, controlling way. What I mean is that no matter what you do in a relationship, the other person has the last word/thought. You can’t control their mind and/or heart. You can do everything right, bend over backwards for the other, and still, if someone’s just not feeling it, it will just not happen. We dumb animals like that, I guess.

What one CAN only do, is to influence people to MAYBE lean the balance to where we want it, meaning: that they like us and choose us. Being a nice person, showing intention, being our true selves and all of that Hallmark-movie crap, so that the other person sees what you bring to the table and decide whether they want that piece or no. Simple, really. Obvious, even.

In a nutshell: be sincere, be yourself, and hope for the best. Avoid trying to be someone you are not, because even in the odd chance that you make something work via insincerity, it will not last in the long term. So, don’t pretend you like volleyball just because the other loves volleyball. 

Learn from my mistake! On a personal and kinda tangent tale, I dated this person for a bit who always chose the movies we were gonna watch. Even though, initially, they asked for my suggestion, I always went “Whatever you want to watch” like a wet blanket psycho, to avoid the stress of maybe choosing something that they wouldn’t like and come across as boring and/or weird. Cut to a few months later, this became a thorn in my side, a point of quiet resentment that eventually (among other reasons) made me end things. I’ve since worked on it, no sweat.

You only get a second chance. 

This is my most personal take and, to be honest, my most cynical. So, feel free to take it or leave it. 

You only get two chances. 

I’m down to be the first to make a move, the first to make first approach, the first to message, and the one to plan our first date. If you are really interesting, you even get a second set to all those. But that is it. I’m going to need some actionable items from your side afterwards.

Not to reference sports again but it’s like tennis: I serve the ball and shoot it to your side of the court. You might miss the first one; you suck at tennis, loser. It’s okay. I’m willing to send another ball your way. If I don’t get it back after that second one you’re OUT. I got no time to play with someone who’s not interested in playing at my same level. (I don’t play tennis, btw.)

Basically, a relationship—especially at the beginning—is a reciprocity dance where we exchange time, effort, and interest. If the balance leans too much to one side, this is not going to work. We are starting a relationship, if we are 25 years in marriage and it’s the third time me being the big spoon, okay, I guess. What? We are going to divorce? We’ve got 3 kids, for god’s sake! But when we are just fresh out of our first coffee date and you are distant, mute, and expectant of me to make another move—please. There are plenty of eyes on this set of bones, baby. I’ve no need to chase anyone. (Yet!)

It’s all about showing interest and initiative. “I’m so busy this week! Sorry,” followed by silence and no “But what about this day or that one,” is an immediate red flag and you’ll be served with my classic “Well, let me know when you’re available! xoxo.” Spoiler alert: You’ll never hear from them again. Good! Bullet dodged, imho. 

This also applies to platonic relationships. Made a first and then a second move and no luck on your side? It’s fine. Not everyone has to befriend everyone. We’ll be totally, irrevocably fine. We’ll live.

Everyone is looking for something different. 

Person on Hinge = person looking for love.

Hmm, yes, kinda, but I feel that’s an oversimplification.

Ask yourself, “why would I want to pair up with someone?” Is it because you feel lonely? Is it because you want to share your life-path with another person? Is it because you are horny? Is it because you want to split rent? Is is because, at your old age, it’s “what you are supposed to do”? Is it because you admire this person and want to have them close? Is it because you want what you’ve seen in movies? Is it because you feel you have so much love to give? Is it because you are an immigrant who’s on that weird line between not being a vulnerable refugee nor a specialized professional and the only way of escaping the limbo is through betrothing a local?… Ahem…

Yes—we, social creatures, are on the prowl to find companionship, but that can take many shapes, especially right at the start of the courtship. It’s good to know what someone is looking for, lest we make the mistake of depositing all our feelings into someone who just wants a casual encounter, for example. Hypotetically. Not that that’s ever happened to me—NO THIS HAS NOT HAPPENED TO ME IM GOOD IM OKAY.

Even when people are sincerely searching for a long-term thing, there are nuances to what a relationship means to them.  Not to be cutthroat about it but I suggest asking yourself and your date what it is that you want from this relationship you might be in the early stages of building, or “a” relationship in the general sense. At a certain point in life, “Idk, I’m just vibing,” just does not do. Even if you are just having fun at the moment, at least have the semblance of a plan. We are not (my Substack stats suggest), after all, seventeen anymore.

Being single is not scary

We are born single and we will (probably and technically) die single too. Let’s not forget that.

We love a relationship. It’s so nice to share the most profound of your soul with someone who understands, admires, respects, and celebrates you. Life is so hard but it’s made easier by having someone on your side to bear the storm and to build something beautiful out of the cards you’ve both been dealt with. Love love! Love wins!

Having said that, being single does not mean that you are a wasted being and can’t have a version of what coupled people have.

Being single is not only okay at any age, but it’s also super fun. You have freedom, independence, spontaneity, and the notion that possibilities are endless and that the best is yet to come. This obviously is not exclusive to being single, those things also (should) exist when you are not. But there are definitely more logistics when there’s two different people involved. Like, what if someone wants to walk and the other bike? There’s compromises to be had!

You HAVE to become comfortable with being by yourself, by your lonesome. Because, for one, being super dependent of another person is unattractive and scary (to me, at least). Like, we are young and smart and able (unless you aren’t, I guess). We are our own’s most important lovers. If we are unable to love and care for ourselves, we are vulnerable to the elements. For two, we will eventually be alone at some point in life, momentarily or for long periods of time. For example, I plan to live to a lucid and mobile 120. What if my lover dies at 80? That’s 40 years I need to be by myself. If we don’t practice our independence, our self love, now, it’ll be harder at 50 or 60, when you find out they cheated on you, they have a second family one town away, and now you gotta get a divorce. (I kid, I kid; that’ll never happen to you specifically.)

(If they’re like me) People will forget, so might as well have fun!

So, apparently in August 2024 I went out on a date with this Canadian 27-year-old I met through Hinge. We had a single date, no sex. I didn’t add notes to my sheet at the time so I have no recollection of this encounter. Terrible. I feel bad.

I believe it’s better to have had a bad date than having a mid date, a grey date, with a person that you don’t remember.

I started going on dates under the pressure of having to make a great impression, to be smart, and funny, and interesting, and engaging. As if this one was THE ONE and ONLY and LAST opportunity I’d ever have to avoid eternal loneliness. Sweaty palms, masks over masks, and panicking at the very idea of a moment of silence throughout.

At some point, probably around date #35, I went “Fuck it!” god and Google Sheets dot com know I’ve been out and about, and the data suggests that this upcoming first date might not be the last. So, whatever. Might as well pick a place that I’ve been meaning to try or that I know I always have a good time at because, at the very minimum, at least I’ll make good use of my energy.

This brain rewire came about, actually, after I found myself being annoyed at the conversation I was having while on a date. I discovered that I had a specific formula that I mostly followed while on a first date. I knew what the beats of the conversation were, and when they were going to come. I noticed repeating the same questions, the same answers, over and over again. Fuck! BO-RING! I’m bored of myself. Shut up, man!

That and the fact that I believe serial daters like myself eventually forget that random date they had with that random person, lifted all the pressures I’ve placed upon me before.

Who knows. Maybe I’m the outlier here and the whole 60 individuals I’ve met in the past almost five years remember me to the minute detail (I mean, I’m certain some of them DEFINITELY do—AYOO!), but I think operating under that framework is still for the best. At the end of the day, dates really are supposed to be a fun time with another human, if there’s a spark at the end of that, well, good!

Anywho, those are some of the top-of-mind takeaways for now. Use them wisely, or discard them consciously. I don’t know your life!

Now that I’m wrapping up, having (again, loosely) dated 60 people and still being single might come across to some as me being the issue. I guess, so. Maybe I have high standards. Maybe I’m stupid. Maybe I just want to have as many experiences as possible before this meat vessel I call body starts visibly rotting and no one whats to take a playful bite.

Two things I’m certain of, though: It’s been interesting, and it’s been (mostly) fun!

Thanks for reading!

PS: Visa expiring in approximately a year and change’s time. If legally Canadian, inquire within.

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