Why Knowing “Exactly What You Want” From a Relationship is Overrated

I need to come clean: I think I was wrong about something.

A bit of backstory: As a self-proclaimed late bloomer in life, I sort of did everything backwards in my 20s.

The first half involved a few long-term, serious and adult relationships before I decided to go back to do a post-grad and subsequently embrace my independence in everything from my career, to living and travelling alone.

And – frankly – I did so also to reclaim my youth and the years that were lost in a relationship that was probably mature beyond my years and level of awareness at the time.

“Why are you going to waste your young, hot years in a relationship, anyway?” one of my girlfriends asked me now years ago when my last super serious, long-term relationship stated to unravel.


It was true. I didn’t want to be “tied down” in my pursuit of confidently coming into my own skin. I had the rest of my life to spend with the person I was going to end up with. Now, it was time to live it up in every way possible, I thought.

So, I did. And I don’t regret it.

I have remained focused on my job, self-growth and – frankly – sucking up the last of my responsibility-free days, and for the past few years, I have passionately written about the merits of waiting to get married and settle down.

One of my main arguments has been that, by this age, I am seasoned enough in the dating department to know exactly what I want in a life partner, what I am willing to tolerate and – most importantly – what I am not (i.e. red flags and deal breakers).


All of my 30-plus single friends seem to echo the same sentiment, along with the accompanying argument that, when they finally find someone, it will all “click” neatly into place and everything will be super serious right off the bat.

And yes, this mentality is all the result of an accumulation of different experiences with and relationships with different people.

I’ve dated as grungy of a struggling musician as Queen West can breed, to the finance type whose suits (and personalities) couldn’t be more rigid if they tried. I’ve been in love, been an asshole, been heartbroken and been borderline addicted to certain people in recent years.

In the process I made a mental note of what mistakes I don’t want to make again, something many of us do:

I can’t be with someone who lacks emotional awareness.
I can’t be with someone who is jealous.
I can’t be with someone who is too critical.
I can’t be with someone who lacks passion.
I can’t be with someone who is too controlling.
I can’t be with someone with a negative energy.
I can’t be with the perpetual party boy.
I can’t be with somebody who is too needy.

All valid points, right?

The thing is – aside from the very few people I have fallen in love with in recent years (that’s another story altogether) – most people who crossed my path romantically were, ‘too’ something.

And many of these “toos” actually had nothing to do with my red flag laundry list (as in, my reasoning varied from “too much of a simple small town boy” and “too uncultured,” to “too unhealthy” and “too nice for me”).

“Is there anyone you meet who isn’t ‘too’ anything?!” My mom asked, before boldly stating that I had become “too picky.”

And maybe she is right. Ok, I guess she is right. But it’s not just me.


Maybe we’re all too damn picky in a culture where most of us are scared to actually love someone regardless of age. You know, in that whole unconditional way.

I fear that my “seasoned dater mentality” has led to defining people by what they aren’t instead of focusing on and discovering the good in who they actually are. In your early twenties, it was a much easier decision to call someone your boyfriend or girlfriend. At this age, it seems so final. We can’t just “accept” things we perceive as unfavourable like we used to.

Now, if I see a glimmer of something I don’t like in someone, it’s hard to recover from it.

Sure, knowing what works and doesn’t for you is essential. But your pursuit of red flags doesn’t have to dominate your dating life. And – in keeping that list in mind – it’s increasingly difficult to fall in love the old-fashioned way, or the way you did in your early twenties when your checklist of requirements didn’t exist.

How many people do you really need to date to know what you want?


Our parents had way fewer options (there weren’t even smartphones, let alone dating sites) and many of them (actually, most of my friends’ parents) have been married for decades. They learned to grow and adapt with the other person in all of their good, bad and ugly glory.

Now, armed with the notion that “we know exactly what we want,” by this age, we are too calculated.

It doesn’t help in any way that, thanks to social media and dating apps, people are increasingly thought of as menu items instead of living, breathing humans.

We discard them after a date or two the same way we send back an article of clothing we order online that doesn’t quite fit right. This seems especially the case for my single thirty-plus friends, as opposed to my twenty-something friends who are totally cool with their “good for now” options.

The thing is, many of my married thirty-something friends ended up marrying their mid-twenties “good for nows.”

Obviously, we can’t ignore that our priorities are a lot different than they were in our twenties; when thoughts of white picket fences (or big apartments) seemed lifetimes away. But we can’t mistake our seasoned dating mentality of “I know what I want” with becoming picky or jaded.

As my mom has always said after every disgruntled phone call, “Give him a chance and focus on the positive, for God’s sake. And talk to me about it in a few weeks once you do.”

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