Three Ways Single People Do Dating All Wrong

Stephen Hussey

Being a single guy in a big city, I’ve learned a few things about what it takes to build a good dating life.

I’ve faced both ends of the dating spectrum. I’ve had “busy” periods where I’ve been on several dates in a week and hooked up with new people regularly, and periods where ABSOLUTELY nothing happened and I’ve been home in my flat on a Friday night wondering, “Am I the only person in London not getting laid right now?!”

Sometimes my dating life is quiet or even barren because I purposely decide to keep my head down (in the non-sexual sense) to focus on a big writing project. At other times, when my life is more balanced, I put more effort into being “single and looking” and my dating life gets rolling again after a couple of weeks.

But what does it mean to ‘put effort’ into dating?


I think a lot of people get the tactics single and dating wrong, so this post summarizes what I’ve learnt about the three big mistakes single people make that lead them into despair and prolonged dry spells.

This post is for those who want to stop wasting time and have more consistency in meeting new partners (sexual or otherwise) rather than waiting to get lucky on the rare occasion. So here are the three biggest mistakes single people make:

1. You think you need to go on lots of dates to have a good dating life

I’ve been in the “dating binge” mindset before, thinking that somehow just going on more dates meant I was doing better at dating. The result? Typically after two hours of going through the motions with someone I’m only sort-of-interested-in over a glass of wine, it ends with me walking back to my place, alone, wondering why I wasted a perfectly good Saturday night when I could’ve been out with friends, or doing something more fun, like reading Kafka, going to the movies, or binging on YouTube videos.

Quantity is not everything. Typically we go on average dates because we get sucked into the trap of thinking it’s a positive sign to be out with someone, when a lot of the time going on a first date with someone we’re not really into is just an waste of our precious hours in the week.

Bottom Line: It’s better to invest more time meeting more people you REALLY like than spending the time going on average/bad dates that don’t really excite you.

2. You think just going out a lot will get you more dates

There’s the classic advice to get out there more, but I think too often people interpret this as meaning “just get out the house”. While that’s a good start, to actually get results a little more strategy is required.

Ultimately, it comes down to two things:

Going to places rich with NEW people ¬– While it’s tempting to go over to your friends house for a movie night with four other pals and convincing yourself that you’re “getting out there”, it’s likely that the only new guy you’ll meet is a pizza delivery boy. While that may be opening scene to many a classic porno, it’s probably not how you envisioned your glamorous single life at this point.

Taking a few strategic risks when you go out – This is other big mistake most people make. Apart from actually failing to get out there enough, the people stuck in the “lonely and single” trap usually get in a rut because they lose their drive to be sociable and actually meet people. They’ll be the ones who go to the club and purposely remain huddled with their friends all evening, or they attend a friend’s party and latch on to the one person they know, or they show up to the new evening class or speaking event, only to keep their head down and never interact with the strangers around them. This is a sure-fire way to blow a ton of opportunities for potential dating.

As a single person, although it’s nice to think it will just happen, it usually “just happens” the most to people who are naturally pro-active and make an effort to connect with lots of people.

This is also why having nothing but coupled-up/married friends can be a disaster for your dating life. Even if they mean well and you love them dearly – most couples have zero interest in meeting ANY new people and will for the most part keep you sheltered in a hermetic bubble with them. Now in my late twenties, the gulf between the mindset of my single friends and those in long-term relationships is vast.

As a single person who wants to get out there, it’s on you to be actively putting yourself in situations where you’ll meet more people in your everyday life. If your weekends are nothing but dinner parties with married friends and nights in watching Keeping Up With The Kardashians with your siblings, it’s time to shake up the diary and make a few substitutions in the calendar (by all means, love and cherish your married friends, just know that you also have a love life to attend to as well).

Which brings me to the third point:

3. You don’t have enough single friends

And not just any single friends. You need friends who want to go out more and actively bring you into new environments. The more you get exposed to other people’s social circles, the much more likely you are to be introduced to someone amazing through a friend of a friend (which is still an incredibly common way to meet people).

Ultimately, yes, if you sit back and wait it’s perfectly possible that your coupled-up chums will introduce you to a lovely friend/cousin/colleague that they can hook you up with. But who wants to wait for that? Who wants their dating life restricted to waiting for things to be delivered and forfeiting their choice over the partners they meet?

Not me. Not you.

When you wait, you end up forced to make bad relationship decisions purely because you wonder, “when will I ever meet someone else?”

You don’t need to think in those scarcity terms.

Go out there – and find some friends who want to be out there with you. Friends who will cheer you on and help strategize with you about how to get the attention of that cute guy at the bar.

You might just find that you feel sorry for your coupled-up friends who are missing out on all the single fun. Or maybe that’s just me.

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