I Pretended to be a British Teenage Boy on Reddit for Three Years: Part 1

I'm not sure why I did it, but I'm sharing it with you.

First, I just soft-launched my book on Substack with Chapter 1 totally free! The rest of the chapters will be paid, so subscribe now to access all of them and my entire archive of articles!

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If you follow me on Twitter, you might know that from the late 2010s to around 2020 or so, I made a lot of one-off benevolent troll posts, often featured on relationships-centered subreddits. These tend to follow a somewhat predictable pattern: crazy OP (original poster) relaying a story about an even crazier significant other or family member, slowly escalating into insanity over the course of the post and culminating in absolutely batshit comments. As an example, my post about a guy who wrote a science fiction book dedicated to OJ Simpson was covered in multiple news outlets. My post about a boyfriend who categorized everything in his life as Virgin or Chad was featured on the Barstool Sports podcast, Pardon My Take. People still tag me when bizarre Reddit posts show up on Twitter, but I’m serious this time: I really don’t do this anymore!

Why was this ever my hobby? Well, it’s fun. Most of the time I would send my fake posts to my friends and family (yes, including my parents- I’m sure they’re very proud that they raised a prolific Internet troll.) I also love making myself laugh and often I write my posts through cackles (most notably, I responded to graphic sexual DMs sent to a Tostitos corporate shill troll account on an 8-hour Greyhound ride, laughing hysterically the entire time.)

Although you’d think I’d be proudest of the trolls of mine that have “gone viral” (sorry that I sound like an early Gen X marketing manager) I’m actually most proud of a long-form troll I started three years ago. His name: Dylan.

Long-form trolls are difficult because they require you to build a semi-believable post history that goes on long enough that people no longer think the account is fake. Basically, folks either think “This is either a really weird person, or the most dedicated troll in the world.” There are no shortcuts. You have to pretend to be another person for years. I always wanted to do this, but never had a persona in mind. Then, I randomly saw a post on Reddit from someone purporting to be a teenage boy asking for video game recommendations. The post itself was unremarkable, but the innocence with which it was posted sparked everyone in the comments section to emit a virtual “awwww” and this post inexplicably got upvoted to the front page. I thought to myself, what if I did that, but the boy was extremely annoying and British?

Enter Dylan.

I started out making Dylan, age 15, ask generic sexual questions like “what is your favourite joke about boobs” and “how many flaps does the average minge have.” Most people on sex-related subreddits aren’t 15-year-old boys, but D&D-playing people in their thirties who like to brag graphically and earnestly about how much cunnilingus they either give or receive, so they were not impressed with Dylan. In order to get Dylan any attention, I would need to find a subreddit that entertained his presence. This proved harder than I thought.

Quickly, I learned that any sub with a majority female userbase would downvote Dylan immediately, preventing him from getting any exposure. Heavily moderated subs like r/relationships would inevitably remove Dylan’s posts, even if they were somewhat realistic.

Dylan started out as a combination of all my favorite British TV shows (I am not British, as evidenced by my occasional misspelling of “humour” when speaking as Dylan. Someone called me out on this and it was humiliating.) I wanted him to be an endearing mix of The Inbetweeners, People Just Do Nothing, Da Ali G Show, and that one chav who mugged Mark in Peep Show.

But Dylan isn’t supposed to actually be a chav- Dylan is white and middle class, but with a strong desire to appear tough and cool. He attempts to achieve this by claiming to be “spiritually Jamaican” and aspiring to be a garage rapper when he grows up.

Initially I wasn’t sure how long this was going to last. Surely I had limited material for this character. Then I stumbled upon r/malefashionadvice, a subreddit for men to discuss fashion trends and get advice on how to dress well. I thought, what the hell, I’ll post here. This is when Dylan exploded. As it turned out, I stumbled upon a group of people who would become Dylan’s biggest fans:

As you can see, Dylan has his own flair. “Dylan.” I actually did not create this flair- the mods of the subreddit did, and they faithfully flaired each of Dylan’s posts this way, but that only happened after Dylan gained notoriety on the sub.

The above post about school uniforms perplexed the sub. I’d say about half the people thought Dylan was real and adorable, and the other half thought Dylan was fake, but hilarious. Given that Dylan already had a pretty substantial post history at this point, I can’t blame anyone for being gullible. What especially shocked me was how kind the users were to Dylan. Even the people who were fairly confident Dylan was a joke still gave him advice, including advice on whether or not he should get married or finish school.

Even people who knew Dylan was a troll spoke to him as if he wasn’t.

Even though the moderators largely liked the post, some humourless bellends reported it for being fake. The post was removed. This continued with Dylan for a while: he’d post an outlandish story masquerading as a request for fashion advice, people would engage with him, and the mods would reluctantly remove it.

Want to see where Dylan eventually ended up and why he had to stop poasting? Subscribe and don’t miss Part 2!

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