Recently, a website called Headlinesagainsthumanity has been doing the rounds on social media. The site seeks to point out how headlines are increasingly used as clickbait, and invites you to guess the real headline between two equally attention-seeking examples. But headline writing is harder than it looks. As with a completed crossword, you may see the result and think it’s obvious, but I promise you it doesn’t seem like that when you have a big black hole in a page five minutes before deadline and have to write something quickly while an editor is looking impatiently over your shoulder.

If you panic, the result can be ambiguous. The term “crash blossoms” comes from a headline in Japan Today: “Violinist linked to JAL crash blossoms”. You had to read the story to decipher it: her father had died in the crash, but her career was blossoming. Sometimes the potential pitfalls should be apparent. While it’s a myth that Guardian reports about the explorer Vivian Fuchs ever carried the headline “Fuchs off to Antarctic”, the following did appear: “Sir Vivian Fuchs for Antarctic” and “Sir Vivian Fuchs at palace”.

My favourite headlines typically involve a play on words, tweaking a well-known expression or quotation, such as “Book lack in Ongar” (funding cuts hit Essex libraries) or “Drop dead, gorgeous” (a feature about office jealousy). Yet both headlines would score very poorly in terms of SEO (search engine optimisation) – the need to include keywords from a story in its headline to help readers find it. If someone types “floods” into Google, it’s not going to take them to theguardian.com’s coverage of the weather if our headline doesn’t include the same word.

You can see the difference in the Guardian’s interview this week with the alpine skier Chemmy Alcott. The paper’s version of the headline was “This is my last Olympics – I’ve got nothing to lose and everything to gain”. No problem in print: a photograph, its caption and a label at the top of the page made it clear whom we were talking about. But the online headline on the same story was “Chemmy Alcott: I would love a Hollywood ending in Sochi”, and for good measure the subheading included the keywords “alpine skier”, “Russia” and “Olympics”.

In the old days (the 1990s) we just used to write funny or apt headlines without giving much thought to the reader. SEO has changed that; and about time, you might say. But the dangers of SEO are that it can make headlines too dull and prosaic – taking us back to the days when the Daily Telegraph’s front page intoned “The Queen in London: phones her Mother” – or not dull enough, seen in the Mail Online’s evident desire to fit a complete story into its headline, so you get this sort of thing: “Children shouted ‘Moobs!’ at me in the street, but now I model in catwalk fashion shows: bullied teenager lost 9 stone in 18 months and now wants to encourage others.” Not very snappy. More words don’t necessarily lead to more clicks.

The technology may have changed but the headline writer’s art is, as it always has been, to summarise the article that follows in a way that draws the reader in. So “Town hit by red sludge goes green”, about an environmental disaster zone in Hungary that has reinvented itself as a hub for sustainable energy, is running on the front page of our website as I write this, and like hundreds of similar examples produced by subeditors every day, it does the job neatly and without fuss.

In my book For Who the Bell Tolls: One Man’s Quest for Grammatical Perfection, my nomination for the best headline of all time is a tie between the Sun and the Liverpool Echo. When the then lowly Highland football team Inverness Caledonian Thistle (nickname: Caley) beat mighty Celtic 3-1, the Sun’s headline – “Super Caley go ballistic, Celtic are atrocious” – echoed the Echo, describing a brilliant performance by Liverpool’s Ian Callaghan against Queens Park Rangers thus: “Super Cally goes ballistic, QPR atrocious”. A case of great minds thinking alike. And, although no one knew it at the time, SEO friendly.