Single. Dating. “Friends-with-benefits”. Coupled.

People like to tell us that one state is desirable over another. And yet, 10 years of working with people in their relationships has taught me that it’s possible to feel wildly fulfilled or totally miserable in just about ANY state between flying solo and a committed relationship.

But that’s not what we’re told.

The cultural story tells us: “Your life will finally make total sense when you meet the right person.”

Actually, it’s even worse than that. It says:

“Get a relationship, or else your life won’t have meaning.” 


This is why being single can be extra tricky, especially for women, who face far greater pressure to prove their worth by “locking down” a steady relationship by age 30ish. 

The cultural narrative tells us that all roads must eventually lead to a relationship, rendering singledom as a kind of purgatory abound with lonely humanoid atoms, hovering past one another until they finally get paired up and can live the rest of their lives in blissful duality.

Well, fuck that. 

I don’t have a dog in this fight. Being in a relationship can be incredible. But being single is also AMAZING and gets taken for granted way more often.

But to do single right, you need to avoid the traps that lead to dating burnout, bitterness, or a feeling like you’re waiting for connection to come and finally give your life purpose.

Here’s how:

1. Stop Forcing Dating

The greatest tyrannical mantra of singles is this: I must find someone else to merge with as soon as possible.

Says who? 

Unfortunately, a LOT of people say so. 

Even as a 30-year-old man, despite not being subject to the same pressures as women, every year I get older I find people have a bemused expression when I say I’ve recently been happy single and pretty much out of the dating game. It’s weird. But it seems to render people genuinely incredulous when you tell them you’re enjoying not having a relationship and don’t plan to have one for a while.

Their loss.

Let them assume you’re hiding. Or you need to grow up. Or pay someone to give you extensive therapy and delve into all the reasons you may be burying a terrifying fear of intimacy.

I’m not saying that getting into a relationship is an unworthy goal. 

I’m saying that once you learn how to love being single and squeeze the juice out of it, you won’t care about finding a relationship UNLESS it already adds to your bountiful, exuberant, jolly, freedom-filled single-fun-fest (think Homer Simpson skipping through the land of chocolate, and you’ll get a picture of where I’m at on this).

And the epiphany comes when you realise: Just because I’m single, I don’t have to date.

Suddenly everything gets easier. You can switch off from all the dating anxiety and throw yourself into all your passions guilt-free and love every second of it. You get PILES of precious free time. You can actually read books. You can fly to your college friend who lives 6 hours away just because you’ve always felt like seeing Budapest. It’s pretty damn enviable.

And just like that, ahhhhh. Relief.

2. Listen To Your Gut

Ok, but what if you are single and also out there dating?

Then you need to be smart about it.

Too many people in the single world waste time and emotion pursuing terrible leads.

They date men and women who don’t invest in them, they spend hours waiting for texts back only to get one-word answers, and they chase intimacy from people who only want attention/sex/validation.

So if you’re single and looking, and want to actually enjoy it (i.e. keep your self-esteem, self-respect, and NOT get burnt out with people in general), you need to listen to your gut more than you listen to what you’d like to be true.

I’ve written many times about how to decide whether to stay get into a serious relationship.

But let’s make it super simple. Ask yourself these 4 questions:

  • Am I REALLY REALLY attracted to them?
  • Do I REALLY REALLY like them and respect the way they live?
  • Do they treat me REALLY REALLY well (and make me feel wanted)?
  • Do we REALLY REALLY want the same things in the next 5/10 years?

Your gut knows the answers to all of these.

If it doesn’t, you’re still avoiding an important conversation you need to have. So listen to your gut and HAVE IT NOW.

Once you start listening to your gut, then comes the hard part…following it. 

In relationships, it knows where you need to go. Unfortunately, what it has to say is sometimes very pleasant and you want to punch it, especially when it says, “Now I want you to go break it off with that sexy person because they clearly treat you as an afterthought and trying to win them will waste years of your life and turn you into a ball of misery and resentment.” 

Your gut will help you drop the WRONG people faster, so you have space for the right person when they cross your path.

3. Be open about whom you meet, but picky about whom you invest in

This one idea changed my entire life. 


Because I’ve seen 10,000 single people do this the opposite way around. 

Most single people do dating like this: They swipe through profiles, go to parties, attend singles events, and in their head is a constant “NO”-monkey, telling them all the reasons they don’t want to talk to that person.

This monkey says things like:

  • He wears THOSE shorts with that shirt?
  • She’s into THAT stupid book?
  • His smile seems kind of cocky
  • I don’t like people who wear beanies. She’s probably an annoying hipster.

And so on, and so on…

Hey, you have standards. Great. But maybe also that monkey who keeps telling you a thousand excuses not to meet people hasn’t always got your best interests at heart.

Because here’s what else happens when that monkey kicks up a fuss and makes you dismiss everyone: you stop meeting ANYONE.

In fact, you meet so few people that the next time you finally bump into even ONE guy you really like, your monkey looks at him like he’s a magical never-ending banana tree, and screams at you “PICK HIM!!! OH MY GOD, HE’S AMAZING!!”, ignoring the fact that those bananas often disappear for three weeks, stop texting back, and then reappear kind of mouldy later saying “hey. U up?” (bananas can talk in this flimsy metaphor).

The smart way to date is to flip this around: Be open-minded about whom you talk to (even if it’s for 5 minutes), but be SUPER picky about whom you invest emotion in. 

That way, you train your monkey to examine the tree a bit more and see if it has strong roots i.e. if these bananas are the real deal or just a clever mirage.

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