My first holiday reading disaster was also my first disaster holiday: a French exchange when I was 14 and every decision I made at every juncture was wrong. Instead of three days, I went for three weeks; instead of an urban sprawl that might at least have smelled like south London, I went to Noirmoutier, an island so tranquil, so isolated, that you could only entertain an escape fantasy for the 20 minutes a day when the tide was out.

I stayed with a minuscule family, all quite self-contained. Some nights, the chattiest thing in the house was whatever crustacea they still had alive in the fridge. Some days, the only words I could understand were the names of meals, which I could have guessed from the time. The loneliness was brutal and the hours immense.

Conservatively, I could have read 21 books and just about survived it, but all I had with me was one, which I had picked up from the throw-away pile at the library where I had a Saturday job. Libraries throw away books for one of two reasons: they have been borrowed so often that they are disintegrating; or they have never been borrowed at all. Misalliance, by George Bernard Shaw, was in pretty good condition.

The play is as short and about as funny as a cracker joke. I read it so many times that I knew it by heart, but I still couldn’t really tell you what it was about. Between the rudimentary politics, the life‑force spiritualism and the self-referential gags about acting, it read like an in-joke he had written in a hurry, having lost a bet.

I overcorrected after that. It didn’t matter what I took away to read, so long as it was incredibly long. My subconscious intervened to sabotage the self-improvement, or maybe just lighten the hand luggage. I left Infinite Jest in a duty-free shop on a ferry and dropped Underworld in soup. I ended up, again and again, with nothing to read but hotel rules and the ingredients on sweetener sachets. I started going away with works in many volumes, like a spread bet – surely I could lose only one?

I went on a resort holiday with Henry Roth’s four-part epic Mercy of a Rude Stream, set in Jewish-Irish Harlem at the start of the 20th century. It sounded so promising. Roth had had 45 years of writer’s block, which he had finally overcome in old age through his obsession with cultural depravity. Surely stuff would happen? The guy I was with hadn’t brought anything to read at all, nor any money or sunscreen.

It was 1998 and everyone else round the pool was reading Irvine Welsh – most of them Filth, some going back to Trainspotting. Every two minutes, someone exploded with laughter. People would gather in the bar at night to do impressions of Begbie. It was incredibly bonding – unless you were packing four gigantic library books with sepia covers, in which case you were a pariah.

Every five minutes, my boyfriend said: “You know what’s good to read on holiday? Something with a neon cover. Something other people are reading. Why haven’t we got any of those good books that people laugh at?” I should have put him in charge of stealing someone else’s Filth. “If you can just get through the awkward family argument that marks the dramatic highpoint of 1914,” I argued, “by 1915 there is incest.” The Roth was actually quite culturally depraved, but that didn’t speed things up.

I want to say I now have a perfect formula for what to take away on holiday, honed over years of mistakes. Unfortunately, that is not true at all; I am still frozen with indecision. But do you want to know what is good? The internet; the sum of human knowledge in your pocket; Kindles. People who lament the end of boredom have forgotten, I think, what boredom actually is.

• Zoe Williams is a Guardian columnist