Lessons From a Scoundrel: How to Write Killer Subject Lines

Imagine a really pretty woman as she walks into a bar with a female friend. It’s probably after work and they’re about to have a drink, a chat, and unwind a little.

Now this lady is awesome. Stunning.

I’m talking Raquel Welch-ish or maybe Naomi Campbell. Or Susan Boyle if you like, I’m really not a judgmental kind of guy.

She’s obviously been approached by many guys in her life, with various degrees of lewd intention. What can I say? If you’re really beautiful, you get a lot of attention. That’s how it works. A good part of that attention has been the inevitable pickup line. ‘Naf’, is what my girlfriend calls it. “Who uses pickup lines, anyway?”

I’ll tell you: lots of guys. You can’t imagine how often men use pickup lines.

And our female friend for the night -let’s call her Suze- has heard them all. The good ones, the bad ones, the cheesy and the hilarious. And to her, they’re all drivel.

This particular evening, the same thing is about to happen again. Some guy gets up and pseudo-casually saunters over. Suze sees him get up, and as he approaches she surreptitiously bares her stiletto-toed pump, ready for action.

‘Hello Kitty!’

“My name is not Kitty”, she says in her usual conclusive way and starts to turn back to her friend.

Immediately, the guy says: “No, but you’re just as cute”.

And Suze can’t help it. Despite herself, she can’t help but smile. A little, but it’s a smile. Yeah it was cheesy, but it was new… kinda funny the first time you hear it…

Now, our friend the charmeur may not be getting laid tonight, but he won the first battle: He got attention, and a smile to go with it. At least he has a chance to talk to her some more, which he would never have had if he’d used a standard pick up line.

How Would You Like Your Every Email to Get Read?

In a way, a subject line is the same as a chat up line. You have about one second to get someone’s attention.

Do it right and you might get a chance to say more, but if you do it wrong, the girls turns away and your email won’t get read. No difference. Sort of.

What you do afterwards, either in the email, the bar conversation, or on your landing page, is a different story. Here we are talking about getting enough attention to be heard.

How I Make Sure That My Emails Get Read

When I pitched my guest post for Question the Rules to JohnnyBTruant, the subject of the email was: “I’m outing you, you fuck”. Then I just pasted the article into the body of the email.

I don’t know why, but I was pretty sure that the email would get read, well, right the hell now. (Note: I had already been in touch with him for months. DO NOT try this one at home. Trust me.”)

When I sent my guest post to James Chartrand, the subject was: “James Chartrand has a crush on me”. Bingo. (Also a pretty risqué one. Use with great caution.)

Erika Napolitana? Yup.

And there’s a lot more, but that’s enough with the names for now.

I’ve had my emails read and replied to, sometimes within minutes, by some of the most busy and popular people on the internet. How? Two things:

1.     I Make Sure I Say Something Remarkable

In the examples above, I said something remarkably outrageous. It’s a personality disorder, I think. Paging Dr. Shallard.

What exactly you say, always make sure it’s remarkable. Remarkably funny, or remarkably interesting, remarkably clever, up to you. It can be anything as long as it’s remarkable.

2.     I Pray to Stephen King

If I remember correctly, Stephen King always writes for one person in particular, and nothing else. I think it is his wife whom he keeps in mind. I’ve played with this technique a lot, and it works amazingly well for me.

When I write copy for a landing page, I imagine I’m the prospect who has just stumbled on the page, reading the words as I write them.

I imagine one single person and I talk to that person. Nothing else. I’m not trying to please everybody. I don’t even try to please a niche. Just one happy reader.

When I write an email subject line, I focus closely on what I think the receiver will want to hear.

I do the same thing with headlines, email headers, blog posts and, ahem… pick-up lines. In fact, at any moment, regardless of the medium of communication I happen to be using, online and offline, I try to hold to these two rules.

If I have nothing to say that I feel fits with these two modules, I shut up. Or try to, at least.

The result? Pretty high communication density.

What about you? What philosophy do you use for chatting up women making sure your emails get read?


  1. Hi Martin,

    I’m the comment fairy!

    This is fabulous article. You’re clearly a fellow rebel and adventurer. I share a similar philosophy for my headlines. I try to entice my reader to want to know more, to want to open the email or blog post.

    I double dare them! Some titles get a better response than others. It’s all about experimenting. In recent blogging memory, “STRIP!” got many comments. Yet, I feel the need to mix them up so my titles do not get in a rut. If every single one follows the same format, then that will get stale too.

    Got some new ideas for titles I’ll be releasing!

    Fun to read your post. Will return again. Giulietta

  2. Thanks Giulietta. I’m very glad it rang true with you.

    Originality is the crux of the whole thing. That’s why Suze ended up going home with me :)

    Seriously: there’s no use in running the same show over and over again. Getting something out that’s new and remarkable is the key.

    If that means you make a fool of yourself? No problem. Shocking? Can work. Ourtrageous? works for me.

    Never rehash old drab drivel.

  3. Stephen King was my inspiration for writing since as long as I can remember, his dedication to the art and writing what he wants are incredible.

  4. I know what you mean! Still, I hope my guess is more or less accurate: I never read his book on writing, I just played with the quote for a long time.

    Whatever, correct or not: it works for me :) I can recommend it to everyone.

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