A writer’s guide to online-dating messaging

Reading Time: 3 minutes

How everything I’ve learned in a 30-year writing career helped me find love.

I’ve been a freelance writer since (yikes) 1999. In that time I’ve had columns in GQ and Readers Digest, written for every newspaper you’ve ever read, plus most magazines and loads of websites, and had 5 books published.

I’ve also messaged, met and married two lovely men.

I’ve come to believe those facts are connected. I did most of my messaging when I was already at my desk, procrastinating. I was already in “writing mode” and approached flirting with men like crafting a feature. They’re very similar. Both lead to great things, if you can overcome the terror, self-loathing and stress.

If you find yourself faced with the Fear of The Blank Page when you have to send a message to someone new (and fanciable), try my tips.

Set a Messaging Time

Just like I have set times for writing (usually after I’ve done the laundry, and am twitchily watching Netflix with mounting guilt), I found it worked well to set aside a specific time to message men.

Setting a Messaging Time stops you from spending your whole life gripped by your online-dating journey. That’s easily done, but it’s a mistake. Not only does it stress you out and cause you to overthink everything, it also gives you NOTHING to talk about on actual, real-life dates. “What did I do this weekend…?” becomes a hideous question when the truth is that you spent 6 hours dithering between signing off a message with 🙂 or 🙂

Your Messaging Time should be a boring time of the week, like a Monday afternoon, or Tuesday evening. If you work from home, do it over lunchtimes. Whatever you do, don’t reply to anybody on a Friday or Saturday night, any public holidays, or Christmas. You can include as many hobbies as you like on your dating profile, but if you send messages when most people are out and about, you’ll look like a chatty hermit.

Send LOTS of messages

If I want commissions, I have to regularly send pitches to as many Editors as I can. It’s the same in dating. You need to show the world that you’re actively looking for love. It doesn’t just net you more replies. It also tells the site that you’re a committed, active member, whose dating profile should be shown to as many people as possible.

Everyone you really like, message them. Everybody you quite like, message them. No, this won’t be a nightmarishly long and involved process, because you will…

Keep your messages short

Unlike when I’m getting paid by the word, short messages are best. Not only are they easier to write (and harder to mess up) they also receive the most replies. This isn’t just my theory, it was backed up by research from OK Cupid. They discovered the perfect length for a first message was 200 characters.

I think short messages receive more replies because they’re easier to answer. A long message is fun to read, but then you develop the sinking feeling that a “LOL!” and a laughing-face emoji really won’t cut it for a reply. Suddenly the long message goes from sweet to grabby, and you resentfully block them.

Use an emoji

Other research found messages with emojis received more replies than messages without. Try it, see if they’re right. 👍

Everyone gets a personal message

As a writer, I have to send tailored pitches. As a dater, so do you.

Some people (men) create a message they’re really proud of and simply copy and paste it, to be efficient. Efficiency is not romantic. Women can SMELL a mail-merge message and will not reply out of principle. 

Don’t get invested

Lots of people won’t reply. The stats are something like only 30% of online-dating messages receive a reply. (Don’t dwell on that. We don’t know how many of those were people not using emojis, the reckless fools.) Don’t see it as a rejection, but also don’t invest too much time or energy into something with such a low return rate.. 

All a first message really does is alert someone to your existence, so they can immediately stalk your dating profile and decide if they fancy you. That’s IT. It’s the equivalent of giving someone a slow wink on the bus to see if they start chatting or just hastily move seats.

Don’t spend too much time agonising. If you do, you’ll soon lose all interest. Like when I learned that some magazines only pay £80 for a 3,000-word story.

Good luck! Let me know how you get on.


Kate Taylor


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