Why is Dating So F*cking Hard?


Because people are hard. Because relationships are hard.

And because dating is actually hard.


It’s a mixed bag of bad timing, missed opportunity, and games.

By luck of the draw or fate, you occasionally come across a keeper – and if that doesn’t work out, the experience is always worth it although the ROI might not reveal itself right away.

Single in Toronto? Let me ask you …

1)     Do you have good personal hygiene?

2)     Have you put yourself out there?

3)     Are you emotionally available?

4)     Are you a decent human being?

5)     Are you pursuing men/women who are actually in your league? (And not chasing Instagram models)

If you answered ‘No’ to any of these questions, check yourself out of my internet office and go down the hall to YouTube. They have videos to help you with items 1 through 5.

If you answered ‘Yes’ to all of these questions, you are likely single due to some personal ‘limitations’ and a sprinkle of ‘it’s not easy to find someone’

It’s Not You – It’s Me … As in ‘You’


The following personal limitations could very well be what’s holding you back from finding – or keeping – someone.

Bad Attractions: You keep falling for the same ‘badass’ or ‘bad-bitch’ and of course the key word here is ‘bad’. We all have that friend – or we are that friend – that just has their head so far up their ass… Like God damn it Kristy, we’re sick and tired of hearing you complain about the same shit every day. Make a logical decision for once – your heart usually follows… and will thank you later. When I have a hard time making the right decision for myself because I am blinded by emotions and my ego, I become my mother: I ask myself, ‘what would I want for my daughter’, then the answer becomes clear. Thanks mom.

Unrealistic & Unhealthy: You want that Romeo and Juliet kind of love… Someone who will kill for you, die for you, ride for you. That kind of passion isn’t sustainable and it can go both ways – love and hate. The same dude that’s playing the guitar outside your window would slash your tires if you don’t pick up the phone on the first two rings.


Baggage: Even the word sounds tiring. Like if you date someone for 8 months who lies about their identity and ends up being married so you tell his wife because it’s the right thing to do and end up living with more trust issues than Drake. Hypothetically speaking… So yeah - it’s hard to let go of heartbreak, betrayal, mistakes – and it’s even harder to rebuild. But you move forward because that’s what you do. Don’t dwell – get well. The lighter you travel, the more space you have for opportunity.

Self-Love: We all have insecurities and sometimes, short-lived ones keep us humble. Stretch marks, cellulite, acne, hairiness, height, length (gentlemen), weight, nipples. It also goes beyond the surface… I.e. not feeling worthy or deserving of nice things. There is no quick fix – only a work in progress. But you don’t have to have it all - to have it going on. You are the only person in this world that you will guaranteed spend the rest of your life with.

In Love With Yourself: Being too picky, always thinking you can get better, and being quick to jump ship when something goes remotely wrong... This is likely due to feelings of entitlement. Daddy’s princess, momma’s boy… Perhaps you’re subconsciously looking for the parent in your partner? Maybe you would rather be alone because… you like it that way… because you’re afraid of having a real relationship. Or maybe you’re just a piece of shit?


Now that we’ve explored some internal factors, let’s have a look outside of ourselves.

Back in the Day….

When it was time to get married, you had a choice between who you knew – and who your family knew. The girl next door, the baker’s son, etc.

Smaller communities = less choice. Less choice = fewer expectations. Men were not equal to women and gender roles were more defined.

Women cook, men eat. Women bear children, men work. Women have intercourse, men have sex.

But now, the lines are blurred – in every aspect.

We have more choices, higher expectations, and more women are pursuing education / entering the workforce than ever.

Gender Roles & Culture


“You know it. I know it. Everybody knows it.” I dare quote Donald Trump…


Women are attracted to men who can protect and provide. Men are attracted to women who are ideal mating partners.

It’s in our DNA, and instilled deeply in our cultures and routines. Recently, gender roles have shifted: old school to new school and all the points in between…

Very valid questions include: Do men still make the first move? Is it socially acceptable for women to sleep around? Can men stay home with their kids?

It’s making relationships a bit more complicated – especially since everyone has a different idea on how things should go.

And then you have a city like Toronto where it’s a melting pot of beliefs, cultures, religions. Everyone does things differently, but they’re all dating each other.

Example: Omar is dating Stacey. Omar’s parents don’t drink and Stacey’s parents are alcoholics. So who’s hosting Christmas dinner?

The diversity is beautiful. But while some might be celebrating, others are holding on to what they know. Neither side is ‘wrong’ per se, but it’s the reality.

We are slowly turning beige – it’s just a matter of time.

The roles might change and the cultures evolve, but one thing is for certain: The Battle of the Sexes.

Battle of the Sexes.

Men and women are not the same. They are equal, but different.

In order to illustrate the differences between men and women, I have created a reenactment of a typical first date experience:


You get home from work at 6:30. Change your outfit 4 times. Moving on to make up because it’s now 7:10. Your date is at 7:30.

Google directions: 45 mins to destination via 2 streetcars. CURSE TTC.

You have to take an Uber if you’re going to get there on time. Uber surge is 2.2X. CURSE UBER.

Grab your purse and run out the door to the elevator. Did you lock the door?

DING. Elevator is here. You walk in and put an argument on pause between a middle-aged couple. Hi…

Looking down now because her boyfriend is checking you out and it’s your white flag to angry girlfriend.

DING. Rush out to street to flag a cab. You’re going to make it.


You get home from work at 6:30. Change into something more comfortable. Eat some chips. Scroll through some funnies.

It’s now 7:00. Your date is at 7:30. You go into the washroom, check yourself out. Flex your arms. You really need to get back into the gym.

Beard is good. Take a look at your junk and decide to clean up a bit – just in case you score. Spray some cologne.

It’s now 7:10. You leave your apartment and stroll into the restaurant 5 minutes early.

Men and women are wired differently. And we have to appreciate this reality despite the frustrations, misunderstandings, and confusion.

In the relationship world, men and women usually want different things, at different times, and all the while, they do all of it differently.

Now put them both behind screens – and strip them of their facial expressions, tone of voice, body language, and eye contact.

Hello online dating.

Stay tuned for PART TWO…