The worst online dating strategy for straight guys

Image by the brilliant Stuart F Taylor

Look look! I’ve found it! After years of sifting through terrible dating ‘systems’ and advice that amounts to ‘treat women like they’re vending machines‘, I think I’ve found the worst online dating strategy of all time. One that misses almost every conceivable mark. Are you ready? Here it is…

You can probably see, immediately, that this is bad. But can you fully understand all the levels on which it is bad? It’s fun to break it down, so let’s go.

Generic chat-up lines are the worst online dating strategy

I have not met a single man who could come up with something ‘funny and smart’ that would seem equally funny and smart to every woman they encounter. This is because women aren’t a monolith, nor are we games consoles: there’s not a single sentence, message or cheat code that works on all of us. If there were, I am such a loudmouth who loves web traffic that I would definitely have let that secret slip in exchange for retweets by now.

Generic chat-up lines aren’t shit because they’re cheesy. The problem isn’t that your generic ‘funny and smart’ comment didn’t happen to be funny or smart enough: the problem is that these kinds of introduction are not fit for purpose. If you’re looking to introduce yourself to a stranger on a dating site, your message needs to do three things:

  1. Show that you have properly looked at their profile, found some thing(s) about it interesting or attractive
  2. Show why you think they might be interested in you and
  3. Ask an interesting, specific question.

And you aren’t going to learn these things from random strangers who haven’t seen the profile in question.

What happens next?

The second reason why this is the worst online dating strategy is because even if it did work in the short term, it’d absolutely destroy you in the medium-to-long term.

When I was younger I used to pretend I liked stuff to impress men. If I had a quid for every time I’ve nodded and smiled through Star Wars references I’d have retired at the age of twenty-five. But having done this I can conclusively tell you that pretending to be someone you aren’t is an absolutely terrible dating strategy in the long term. In the best-case scenario, your date will realise swiftly that you’re not who you’re pretending to be, and call it quits before you’re in too deep. Worst case scenario? You manage to keep up the pretence for just long enough to fall for them, then come to your senses a few years down the line whereupon you realise you’re in too deep with someone wildly unsuitable, and it takes a mountain of effort to escape. I have luckily never fallen into this ‘worst case’, but the thought of it makes me shudder.

I’ll let you in on my own dating strategy, if you like, which one day I’ll try to write about in a little more detail: my dating strategy is to try and be as ‘me’ as I possibly can be. On my profile, in video chats, and everywhere. I don’t tell people what my job is, but other than that I slightly turn up the dial on ‘who GOTN is’ so the guys I chat to are met with an oversexed, sweary woman who is interested in neither Star Wars nor 5-season Netflix box sets but has Very Strong Opinions on politics and jokes that you may or may not find funny. There are plenty of men who’ll be turned off by this woman, which is great, because those are exactly the men I want to turn off. I want to find men who are excited by women like me, not ones who are impressed by a costume I’ve put on to appeal to as many dudes as possible.

So using other people’s personality, wit or smarts as the basis for your first message, even if it does get you a few more replies (which I have to stress it probably won’t), is the worst online dating strategy in the long term, because it means you have to try and be that person for as long as possible. Exhausting. Dating is, after all, supposed to be fucking fun.

I want to understand women, so I’ll listen to men!

Final point, and I think it’s the cherry on the cake of why I believe this is the worst online dating strategy: if you want to know what straight women want, the best people to listen to aren’t straight men, but straight women.

More helpfully, if you remember point one about how women are unique individuals with different needs and desires, the best person to listen to if you want to get with a woman is the exact woman you’re trying to chat up. You want to get with a woman who is sporty and works with animals? Listen to her! She’ll probably know best how to get her attention. Want to hang with that woman who mentions dick three times in her profile and has a photo of herself scuba diving? Listen to her!

Do you see where this is going?

That’s right! It’s a very long and tortured way of making the same sledgehammer point I make to anyone and everyone who is struggling to get responses on dating sites: read people’s profiles, pay attention, and stop looking to match with just anyone – seek out the people you specifically like, and listen to them! If you’re really nervous and unsure what to ask, but you are incredibly intrigued by a particular woman, you could do a hell of a lot worse than:

“Hey, I love your profile – am really intrigued by [interesting thing she does]. How did you get into that? Sorry if this message comes across as clumsy – I’ve tried to rewrite a few times because I’m super-keen to get it right but I’m a bit terrible at this messaging thing. But because you [something else about her profile that you think is cool], I’d kick myself if I didn’t at least say hi so… hi!”

Remember, though, you should only send a message like this if you genuinely are a bit clumsy and bad at messaging, because above all your message needs to be true. Don’t just copy/paste this because I’ll get a bunch of women on dating sites coming for me (and rightly so). I’m just making the point that it’s OK to be honest – you don’t need to copy ‘smooth’ messages from men who are better at dating than you, because you’re looking to find someone who wants you, not some random cheesy stranger who thinks of themselves as an ‘alpha’ and believes they have ‘solved’ women like we’re Rubik’s cubes.

I know, coming up with personal messages is time-consuming, and it’s often incredibly hard. More importantly, I am not going to guarantee that if you craft the perfect first message you’ll even get a response: I have about two dozen genuinely lovely, interesting guys sitting in my dating site inbox at the moment, but my life outside the blog and dating continues to crumble in remarkable new ways with each week that passes, then London went into Tier 2 lockdown so chances are many of these lovely men will languish in my inbox unreplied-to and unfucked. I don’t say this to boast about numbers, just to reassure those of you who aren’t getting responses: the balance in straight dating genuinely is incredibly skewed, and it’s more than possible that the women you wrote lovely messages to have just been caught up with other life stuff, lockdown woes, admin or something else. Make your messages personal, but try not to take it too personally if you don’t get a reply. The world is an absolute shitshow right now, and not a single one of us is at the top of our game.



  • oxyfromsg says:

    i can feel that pain behind my eye coming back.
    Wanna talk to a woman? Talk to a woman.
    Its not rocket science.
    Dont use strategy, use being you.

  • Kafka says:

    Hey, you’ve just discovered my super-secret formula I’ve used for great effect :-) I did use to have a template message: it had 2-3 sentences about me, 2-3 sentences about what I liked about her profile and I tried to ask a specific question. I did find my wife, so it worked for me, but there’s a big caveat. I agree that’s important to listen to women – if only they’d tell anything! My experience was that most women left their profile more or less empty, especially those under 30. I guess their age and kind of genitalia ensured a firehose of incoming messages, they didn’t need to do anything more to get requests. More mature women tended to write something useful, but after a month I literally ran out of possible women to write to (and I live in a fairly large city). I was about to let my subscription run out, the message I sent to my future wife was one of the last messages I ever planned to send on that site. So while I agree with everything you’ve written here, I’d like to add to guys that if they’re looking for women under 30, live in some rural region and/or are below 180 cm – don’t get their hopes up.

  • Folly says:

    I second all of this.
    And even if the guy would not interest me according to his profile – if he had gone to the effort of a three sentence personalized message, he’d get a reply.

  • Faustian says:

    I presume that bloke also wrote the profile he was catfishing with? Did he steal someone else’s pics too?

    So not only is it a man listening to men it’s a man listening to men responding to the a man in the first place. I think we’re probably degrees closer to Kevin Bacon than any women in this situation (assuming the profile creator was targeting only men).

    I do love looking at dating profiles like I’m in a nature documentary though and wondering if the psychology at play is effective or not to other people. I find it terribly off-putting if someone rattles off a list of things they own for example, or is overly negative and tells me all the people on the site are bastards or perhaps they feel the need to clarify that their kids are more important than random dates on OKCupid. I do like someone who laughs at themselves, or laughs at me.

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