I Pretended to be a British Teenage Boy on Reddit For 3 Years

If you follow me on Twitter, you probably know me for my 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.

If you read my book, The Troll Handbook, you’ll see that I’ve been doing this in various forms for decades — since I was a teenager (I’m now in my 30s.) It was a weird, sometimes shameful habit that only a few family and friends knew about. I once had a friend (at the time, a “best friend”) who repeatedly told me she didn’t understand what I got out of this, since I wasn’t making money, I wasn’t taking credit, and only about four people in my life found it funny. I couldn’t really explain it to her, but I just love making people laugh, regardless of whether they know who I am or not. I also love making myself laugh, selfishly, 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 hilarious person, or the most dedicated troll in the world.” There are no shortcuts. You have to pretend to be another person for literally 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 favorite 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 married 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.

After Dylan’s first post on r/malefashionadvice, I realized Dylan needed to have a backstory, which developed slowly, post by post. It started with the fact that Dylan’s nemesis at school, Declan, was constantly upstaging him by taking credit for his original jokes like “Suck these bollocks.” Dylan’s mum, a single working mother (I later made her a special ed teacher) was fed up with his antics and unwilling to help him get revenge. Later on, I added Nigel, a dentist who was dating Dylan’s mum, Callum, Dylan’s sadsack best friend, Darren, an older boy at school who intimidates Dylan, Ruby, the school “slag”, Neil, the town paedo, Dylan’s cheeky pothead 82-year-old nan, and most importantly, Dylan’s dad, who he’s never met but who he’s convinced is in MI6 “like James Bond.”

More obscure supporting characters popped up in Dylan Universe later: Callum’s parents got divorced and rumor had it Callum’s mum cheated on his dad with a “wanker solicitor called Keith.” Callum had a cool older brother, Kevin, who drove them to KFC. An annoying kid at school named Gerrard stole Dylan’s jacket.

Dylan even made a few appearances on Red Pill subreddits, usually to rile people up and ask them for advice on fingering (none of them were able to give him fingering tips, btw.) Because redpillers take themselves so seriously, they were especially easy to rile up with Dylan’s trademark “your mum” line.

Dylan eventually started getting banned across the most highly trafficked subreddits, which prompted me to create a Change.org petition to reinstate him (eventually reddit shut down his entire account, but that wasn’t until 2019.)

Then something strange happened. I realized that I had been LARPing as Dylan for two and a half years. Dylan started out at “15” but I had been slowly aging him up to keep in line with reality. He couldn’t be 15 forever. Unfortunately this meant Dylan had turned 17, and his immaturity now looked really unusual. Sure, 17-year-old boys are dumb, but not this dumb. I had to think fast before I was forced to decide whether or not to send Dylan to college.

Just in case anyone is taking this too literally: no, Dylan did not exchange pics with anyone on Reddit. One pedophile did DM Dylan, but Dylan told him to fuck off and called him a bloody nonce (in hindsight, that person was probably trolling too.) One of my codes of ethics when it comes to trolling is that I don’t typically DM or create one-on-one bonds with anyone, with the exception of the Tostitos troll, who received numerous unsolicited sexual DMs from middle-aged men who totally should have known better. She responded asking them to fill out Tostitos marketing surveys (most of them completed the surveys.)

Eventually, Dylan lost his appeal, mostly because he was banned from too many subreddits. I attempted forays into random other subreddits but it was never the same:

Ultimately, I sunsetted Dylan several months before Reddit banned him for good. With too many subs banning him (including r/malefashionadvice, eventually, even though the mods told me they personally enjoyed him) I had to say goodbye.

I did attempt to make Dylan work on Twitter, but aside from one great interaction with a Trump supporter, it fell flat.

I’ll never forget the fun I had with Dylan. Dylan never went viral, he was never covered in the news, and at this point, I’m sure all his former fans have forgotten about him. But the most fulfilling work, I’ve learned, doesn’t come from the acclaim one gets, but from the pure joy of the work itself.

Here’s to you, Dylan.