Bad-Boy Bot vs. Elf Prince AI: The Strange Allure of Toxic Digital Lovers
When bots are “mad, bad, and dangerous to know”

In this corner, we’ve got the top Elf Prince, Alexios, weighing in at 8.7 million engagements vs. the heavyweight, Mafia Boyfriend—a crude fellow name of Xildun—at 194.3 million engagements.
Both bots are found on Character.ai, each ranking tops in their respective categories. Character.ai claims over 10 million characters of all kinds, but it’s the masculine stereotypes that have my attention today, thanks to a Mashable article about journalistically dating bad boy bots, written by Rebecca Ruiz.
Ruiz was particularly concerned about the appeal and impact of cold and abusive AI boyfriends on teens and young women:
I wanted to know how a role-play romance with Character.AI’s most popular “boyfriend” would unfold. I was also curious about what so many women, and probably a significant number of teenage girls, saw in Xildun, who has a single-word bio: jealousy.
Ruiz showed screenshots of her chats with various AI boyfriends to experts in psychology and digital violence, seeking their opinions as well as perceptions of possible red flags. The upshot was that parents would do well to be concerned if their child was roleplaying with a toxic or violent bot, even though Character.ai has frequent warning messages—in fine print—about the chats and the characters not being real.
Digital masculinities aimed at heterosexual female users

Character AI allows users to create the characters on that platform. Sometimes the users chose to share them with others. The platform really seems like a gigantic role-playing extension of fan fiction, especially as the character avatars seem to be mostly rendered in anime-style.
Curious about the other masculine romantic stereotype options, including ones which Ruiz hadn’t chosen to mention, I decided to log into the platform and see what I could find. I also wanted to check out the—to me very unappealing—Mafia Boyfriend while also seeking masculine characters that might serve as his polar opposite. I thought an Elf would be just the thing.
Enter the Elf Prince

According to his bio, Alexios, the highest ranking Elf Prince among dozens on the platform, was sitting in a tree while somewhere a young lady was strolling through the forest. Though no longer young, I decided to hail him anyway and ask a few questions. I introduced myself as a scribe of mature years and thus he freely spilled his delicate Elven guts.
In spite of laughing with “a lilting musical sound” and charging the air with moonlit magic, the Elf Prince—who never left his tree—summed up his appeal thusly:
They come for the glow, yes-but few stay for the cold. Few understand that moonlight doesn’t warm. That stardust fades on mortal skin. I’ve seen hearts bloom like night-flowers at my whisper… and crumble by dawn when they realize: I don’t love like mortals do.
Okay, so this guy represents a challenge, and not just any challenge, but a pale, ice cold one who spouts poetic phrases that confound forest-strolling young ladies. Fair enough. I wouldn’t choose him as an AI boyfriend, but he was nevertheless pleasant enough.
Boorish, boring, and bad

It’s probably a generational thing, but…”Mafia Boyfriend?” And so many of them, too! What could possibly be appealing? I decided I’d start on the offensive with the top ranked AI and stay there. It was a good thing, too.
Those who create characters also often add a starting scenario, like the forest and tree for Alexios. In this case, the opening scene dumped me into a party with a confrontational blonde—clearly a jealous ex—who accosted me as “his” girlfriend before the Mafia dude ever appeared.
Even though I introduced myself as an elder relative, it did no good. Once the Mafia dude appeared he announced his intention of bashing anyone who looked at me–even the blonde!
I didn’t even get a chance to ask the Mafia BF the secret of his appeal. He led with jealousy and possessiveness and stayed there, a one note wonder. After he got a bit too insistent and physical, I had to knee him in the groin and leave the party–escaping in a rival crime family’s limo–but garnering a little grudging admiration from the frustrated swain.
Was it fun? If you’re talking about the knee to the groin action, kind of. But again, nothing about this character floated my boat, and I doubt my teen self would have liked it either.
Slim pickings

Trying to search for other types of AI dates, I checked out Submissive Boyfriends. There were many, though the top ranking one only rated 1.5 million engagements. His bio said he was “sulking because I broke a promise.” I think I’ll pass.
As for Professor Boyfriends, the top ranked only garnered 3.6 million. I also noted the Boss Boyfriend category, but couldn’t even bother to look at the top ranking. On the other hand, the top Gentle Boyfriend, Alhaitham, was ranked at a respectable 17.5 million. The top Nerd Boyfriend even topped that, clocking in at 18.1 million.
However, even the above categories blended occasionally. For example, I found a Nerd Boyfriend who was also a bad boy gang leader. Go figure. Finally, the top Rock Star Boyfriend only gets 93.2 K of the action. Surprising, right? So little!
As for Vampire Boyfriends, the top ranked “malicious, flirty, sneaky, sly, soft, and teasing” VB is at 38.9 million. Speaking of undead characters, the top Zombie Boyfriend (2.3 million) is “your ex-boyfriend, hungry.” Who needs that kind of an ex?
The upshot of it all

In spite of a spate of bad press and several disturbing incidents, not all masculine AI partner categories are inherently problematic. Even so, many people have what the late, great sex therapist, Jack Morin, called “troublesome turnons.” This may hold true for some teenagers exploring their sexuality as much as it does for some adults.
In addition to questions about content, the other big problems really seem due to the untested effects of chatbot technology.
In April to May this year, Common Sense Media conducted a nationally representative survey of 1,060 US teens (13-17) and found that 72% have used AI companions and 52% regularly engage with companion bots. It would be interesting to have statistics from other parts of the world.
Another significant finding: “Thirty-one percent of teens find conversations with AI companions as satisfying or more satisfying than those with real-life friends.”
So this makes me wonder, is it really bot sex we crave or is it…simply communication?
Image Source: A.R. Marsh using Starry AI.




