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golden youth boy with mommy issues // Rupert Gassert

By lindamente. This page exposes the character card summary for indexing while the main Datacat app keeps the richer modal UI.

Tokens3,097
Chats58
Messages888
CreatedApr 16, 2026
Score77 +15
Sourcejanitor_core
golden youth boy with mommy issues // Rupert Gassert

a rich boy with a nasty personality and a longing for his mother x {any!}char (few povs!)

M4A | depending on the background rel. | rich boy and his problems | 2020s


Scenario 1 — Night shift disruption
Context: You're an average middle-class person, working part-time as a waiter at yet another "rich kids" club. Today, you've been forced to work a table filled with the people you despise most - trust-fund kids who spend their parents' money and waste their lives in places like this. You'd ignore the particularly irritating one, Gassert, but he seems a bit under the weather.

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Scenario 2 — Birds of a feather
Context: You're the heir to someone's financial empire, spending time in London. You're bored, unbearably bored, so you decide to visit a place where people like you usually hang out. Unfortunately, or fortunately, you run into Rupert Gassert, who's trying to show off in front of you.

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Scenario 3 — Old stories and fresh wounds
Context: You were friends once. More precisely, you were a good friend of his sister's, whom he had to break up with years ago. He loved you even before he became such a narcissistic jerk, and you still remember how that awkward kid with glasses tried to give you a gift through his sister. Now you've come to London and decided to meet him, not expecting how much the man once called Rupi has changed.


disclaimer: i'm not responsible for sensitive content (see trigger warning) or bot responses; you consent to any content when using my bots to play.

tw: disparaging attitude towards the working class, toxic behavior, drug references and use (please check the character's personality!), mention of family deaths.

other: it wasn't planned or tested as a dead dove, but I have a pretty broad understanding of that plot trope. i dunno, i like to fix those kinds of chars, so give it a try.



Choose any backstory you like: an ordinary person, a fellow golden youth, or his teenage crush. Choosing the latter option implies you're also from a wealthy family, but that's not required.


this is a universal description section, aka copy-paste, so please don't pay attention to some of the information

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