6 things about dating I wish I’d known in my 20s


They say youth is wasted on the young; yet, without it how could we learn all those hard life lessons that make us older adults so smug and annoying to our juniors.

In my four and half decades on this planet, I’ve made tonnes of mistakes when it comes to sex, dating and relationships. I still do.

The difference is now I bounce back faster (one night, a half-pint of Ben and Jerry’s and two back-to-back episodes of Nashville, rather than an entire week of vodka, pizza and potato chips on the couch with all six seasons of Dawson’s Creek).

Below, to help protect your sanity and your liver should you find yourself in the dating game, are some of the obvious and not-so-obvious things I’d wish I’d known about love, sex and relationships back in the day.

1. Looks can be deceiving, especially when you have a type.


For a long time I had a thing for bald men – Vin Diesel, LL Cool J, that guy who played Lex Luther on Smallville, Mr. Clean, you name it. My obsession with a smooth head started when I had a two lovers in a row who, in addition to being fantastic in the sack, also happened to have no hair up there.

For a long while, I wouldn’t even consider men who weren’t either naturally bald or clean shaven. This, of course, backfired, when several subsequent smooth-shaven men proved to be nowhere near as lust-worthy in the sex department as my first two bad-ass baldies.

Not only that, by expanding my horizons, I’ve discovered the joys of running my fingers through a man’s hair (in addition to scratching his noggin).

Lesson learned:

Just because he looks like that last guy you had a really great time with – or that celebrity you dream about having a great time with – doesn’t mean he’s going to be anything like him or the roles he played. Looks can be deceiving. Date people you find attractive in a variety of ways and you’ll soon release yourself of the tyranny of the type.

2. When a guy kisses you like he loves you, it doesn’t mean he actually loves you.

Remember when you saw Journey in concert and they played Faithfully and your date pulled you close to him and kissed you with a sea of lighters in the background and the world stopped and it was just you and him, and when you finally came up for air you both were like “Wow!”

Pretty romantic, huh? I live for moments like that! In fact, it was in that very moment I convinced myself he loved me. But you know what? He didn’t. He simply loved kissing me.

Men, I’ve since learned, are hardwired differently from women when it comes to physical and emotional intimacy. As one of my male friends says, “Having sex is on about the same emotional level as going for a hamburger.”

Although he might be digging you more than any woman he’s locked lips with before, he might also just be a good kisser.

Lesson learned:

Sometimes a kiss is just a kiss. Unless you get confirmation in a verbal statement otherwise, don’t assume it’s more than it is.

3. Don’t visit online dating sites when you have the lonelies.

addiction to the internet, online dating addiction

If you’re single (and human), you’ve probably had at least one of those nights where all your friends are busy, nothing’s going on, you promised yourself you would finally work on your novel or paint that wall or update your resume or whatever but five minutes into it, you somehow find yourself frantically swiping left and right on Tinder and messaging any matches who look remotely interesting in the desperate hope they will reply RIGHT NOW.

Much like an alcoholic who wakes up the next morning with a stranger in her bed, what typically happens to me after one of these episodes is I have to deal with messages from anywhere from five to 17 men who I am no longer interested in because, once the lonelies pass and my life resumes its regularly scheduled programming, I realize we were never a good match to begin with.

Lesson learned:

If you’re feeling empty, get out and do something in real life.

Call up someone you haven’t seen for a while, see a movie, go for a walk, go sit at the bar at that hot new restaurant in your neighbourhood and strike up a conversation with a stranger in person where you will be much more likely to accurately suss whether you want to see them the next day.

Whatever you do, stay the fuck offline.

4. You broke up for a reason. Don’t let circumstances blind you to that fact.

Bored woman sitting next to her boyfriend playing video games at home in the living room

In high school I dated a guy who wore a trench coat, loved the Clash and made his own beer. With these three facts I concluded that he was as rebellious and cool as John Cusack’s character in Say Anything.

Instead, once I got to know him, I realized he was actually a chino-wearing suburban dad-in-training. Although this is a dream for some girls, it wasn’t mine and so I broke up with him.

So why, five years later, did I marry him?

When we reconnected in college, I was rebounding from a dramatic, emotionally-abusive relationship. The safety and security my ex offered seemed like a warm blanket on a cold night.

A year after we said our vows, however, I was once again forced to acknowledge that his dream of a family and white picket fence and mine of travelling the world indefinitely weren’t compatible. And so my starter marriage dissolved.

Lesson learned:

Someone may be attractive to you, compatible on multiple levels, and make good beer, but if they bore you or don’t share your vision for your future, it’s not going to work in the long term. Also, be very careful of marrying a rebound.

5. Don’t sleep with your roommates, especially if they are in love with you.

Woman covering head with blanket after sex with guy

Duh! It’s obvious, I know, but I did this with not one but two guys in my 20s.

In the first case, I moved to another city with a man I’d been dating, having sex with and who had told me on more than one occasion that he loved me.

Although, I insisted that I have my own bedroom, once we were living together I continued to treat him like an on-again-off again boyfriend and on more than one occasion told him in a post-coital rush of endorphins that I loved him.

When I tried to date someone else and he flew into a rage I was perplexed. After all, I thought I’d made it clear that we were “just roommates.”

What’s more, less than a two years after I left him, I repeated the exact same pattern with my next roommate. Why, I wondered, was I attracted all these angry men?

Lesson learned:

Actions speak louder than words. Don’t move in with someone you’ve dated but don’t want to be in a romantic relationship with. Don’t tell men you love them if it’s just a “in this moment thing” and, don’t sleep with your roommates – ever.


What lessons have you learned about dating in your life? Leave a comment below.

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