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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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14 Replies to “Three Ways Single People Do Dating All Wrong”

  • That’s perhaps my biggest challenge – new places to go. I tend to lament the fact that I’m out all the time, but there does need to be more variety in the places I go (she begrudginly admits) ;)

  • I went to a Trivia night which ended in dinner at a pizza place, all with friends I have only just met in the last month (except for 1). We realized, halfway through the night that every person was single, which completely changed the dynamic of the night. You could tell that some had been friend zoned, and that some were interested in others… the positive thing was that we were all out, connecting! We had a blast.

    I have loved getting out more and hanging out with new people. Just have to switch on the flirtation a bit more for dates. Haha



  • A single guy in a big city, aah I love the cliche. You are absolutely right, as always, but you are never smug and your very self deprecating humour shines through. Your blogs make me smile and who can be sad when there is so much choice out there. The world is our dating oyster, which the smug, stay in marrieds can’t say. How wonderful is that?! xx

  • My theory on dating is don’t ever do it. Xx I’m coupled, and you totally want me as your friend if you are single. I may get you in huge trouble, but it’ll be fun. I stay in contact with guys as friends… Nothing serious. Just a message here and there as you would any friend. If I have single girlfriends, I can introduce them. Even if I knew it wouldn’t work out with a potential (like one was heading 4 hours away to get a PhD and was way too young), I was always game to hang out when it was convenient for me. That one – we have a lot of fun on snap chat and he’s a science nerd like me. We make each other laugh and talk about microbiology. I’d have a belly dance class downtown so I’d ask a “friend” to get a quick drink before I went home. Or, I was gonna hit up a nature trail so I’d ask a “friend” to bring his dog and walk with me. I refused to date actually for a long time. I’d go with a “friend” to the shooting range. One guy – we’d always coffee shop it up and say really sexy things to each other in Spanish or talk about ppl and no one would understand :) That’s kind of a rush actually. These were all potentials … Ppl I like and admire and have something in common with. It wasn’t all interview-style date-like, then – “I’m not interested.” Nobody got weird. I never slept with any of them. I like it this way, but some guys get angry if they really want you all to themselves and you are out dancing with someone else, but that was boring and I didn’t have time for it. I didn’t kiss any of them. Well maybe 2, but just for fun. As long as they were cool and didn’t get weird they can still text me. A lot of the ppl I wanted to date I seriously admired, so I tried to build a friendship to test them out and see if they were legitimate. I did it with lots at the same time so I didn’t have time to get serious with just one – and I acted in a way that I’m proud of, as long as I fairly sober ;) We never had to break up unless we wanted different things. We didn’t just rush into a lame relationship without knowing each other and realize it was wrong; I can still talk to them casually whenever I want – kind of sexy. I feel like seeing lots of ppl casually helped me realize what I want in a relationship and in friendships, so I can solidify different friendships with those who have the qualities I admire. What do you think of friendships with the opposite sex?

    You should bring your first dates out with your friends and tell them to bring a friend. If it’s boring, do shots. Lol. You are right; dating is serious and lame and should be reserved for ppl you are seriously interested in. I’m glad we’re not dating if you’d rather be at home watching you tube videos. Lol. Ouch! Technically though, you can get to know lots of ppl and not date at all ❤️ which is maybe the theme of #3… ish.

    I enjoyed reading this. I felt like you were saying date less, hence the long comment. But I think we are saying the same thing in a different way. Keep it coming Hussey. Xoxo

  • Amazing article as always. Seriously though, you need to put a warning on these things. I nearly choked on my tea whilst laughing at some of your puns.

    Already looking forward to the next article.



  • Well, sometimes (not always) you just have to say yes to find out;)
    What helped me is surely being more sociable.
    Going out with a group is great – you have the core (the guys who stick together) and the ones who love to meet new people.
    That’s the ones I can go out with in groups or just us two – even if engaged, she’s keen to meet people, everyone’s doing her thing and we’re still in there together.
    I recently noticed: Your advice did sink in somehow: I’m way less inhibited to make remarks, lately talked up a guy this way in passing – wasn’t even intentionally – and hours later (he stuck around)he approached. Wasn’t a big deal, but he remembered it quiet well! Huh
    Another useful thing: As I’m a reader I always have a book in my purse. As long as it’s not 4am in a club, if I happen to be out alone that’s a good balance for me: I get to chat up people, meet new ones and some I know, and if everyone’s busy with themselves or I need a break I catch up on some reading. First it’s my nature and what I like and need, second people get relaxed as I’m leaving them space and I have mine – and third, it can lead to some interesting conversation. On the book or other topics not less interesting – I’m not impolite, I put it down if necessary:)

  • Another great article from Stephen! I especially support the idea that we should choose more carefully who we go on a date with – spend more time watching the person behave – if they are from our friend circle or colleague, before we ask them out. The more you find in common before that, the more you will have to talk about on your date.

    There is another topic which I am very interested in as well. What about people who are not ready for a life-long commitment yet? Let’s say you are in your early 20’s or just not ready for a marriage yet – should you go on any dates at all and make any relationships at all at this point? If yes – with what mentality in your head?

    This is a question I am truly wondering about, because in my early 20s I had some relationships which were – “for the experience of it” or “he seems interesting” – but they all ended in a heartbreak for one of us, so I have the feeling I am truly getting something wrong about love life and dating, so I have been avoiding guys in general for the past 6-7 years. I am currently 27 and not ready for marriage yet. I am currently working on a very important project, but I wonder in a year when this project will be completed – should I at all have a dating life or just stick and party with friends until I decide I am ready for marriage?

    It’s probably a stupid question, but the answer somehow eludes me. Since I don’t want to repeat my mistakes from before, I would really appreciate if Stephen or Matthew shed some light on it in a video or article for the women who are not ready for marriage yet.

    Thank you very much for your attention guys! What you are doing for the female audience is absolutely remarkable – you are literally saving people’s lives!

    Keep up your great work!



  • Yes, yes and YES! Also, if I were to add a 4th it would be “relying too heavily on dating sites.” Especially in a city rich with young adults and lots of single people, this happens and deters us from making an effort with people we meet in-person in our social (or regular) life. I vocalized this to a group last week after a single guy announced how he kept getting matched with people he’d met in various circles (and wondered to myself why he didn’t just ask them out in-person). But I’ve been guilty of it too…

    Finally, thanks for using a pic that shows some diversity.

  • Why is a first date where no chemistry appears a waste of time???
    When I read your article I imagined that after your date both go home and are upset that it was “a waste of time…”
    If you guys cannot appreciate that the other person has the same expection about the date as you and both do their best to be interesting and polite to each other, you should consider that it is also up to you to create a nice evening or afternoon or just one hour in a café to at least have fun together like friends. Last but not least you can be proud to being brave enough to give yourself a new chance. That means that in my eyes every each first date can be a success but only in case you are willing to see it positive as a next step into the right direction.

    1. Its awesome to have a good attitude, but being abit more selective if you are dating everyone can prevent burnout. I’ve been there. Dating can become another job. I already have a job.

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