DM: I think it's about time to meet the bride-to-be, Princess Mi Amore Cadenza.
Shining Armor: "Cadance" to her friends.
Twilight Sparkle: You mentioned all this before the last time we were in Canterlot. She was my babysitter, right?
DM: Technically, it's called "foalsitter." And yes, that was the idea.
Princess Cadance: Interesting. What sort of relationship do you think we would have had?
Twilight Sparkle: Um... Well, if it's anything like how I was as a child... I didn't really *need* babysitting. I was quiet and did all my homework on time.
Princess Cadance: No need for scolding, then. Perhaps we would've made fast friends!
Twilight Sparkle: Well... I don't know how receptive I would have been to that. At the time.
Princess Cadance: So preferably not overbearingly positive, then.
Twilight Sparkle: Yeah. Yeah, I guess.
Princess Cadance: Done and done! You had an empathetic, patient babysitter who largely left you to your own devices.
Twilight Sparkle: ...Thanks.
This is sort of another big moment where I realized that my FiD-Twilight has a lot of divergences from show-Twilight. You can chalk it up to the show having additional in-narrative years of positive character development, but even then, a lot of the little decisions I've made have led to a character that's both familiar and very different.
I always enjoyed the flashes where the two Twilights intersect again, because that's usually where the Twilights get impulsive with magic. I still laugh at the comic page where Twi uses the Fireball spell to resolve a problem.
My second 3.5 Campaign was set in Faerun, and our party druid was the adopted sister of my Dwarf Rogue/Barb. She was, genetically an Elf, but as far as the pair of us were concerned, she was a Dwarf. We didn't mention the ears, height, or lack of facial hair, and neither did anyone else who was attached to their kneecaps and wished to remain so. Made for some glorious interactions, especially the couple of times we had to introduce new players mid-campaign.
My fiancé and I like to make characters together. In this case, Janice was a Div spawn tiefling, born into high society, and generally hated by her ashamed family. Krath was a rakshasa spawn tiefling, has a horrible relationship with his dad, and was an accomplished swordsman, thief, and arsonist. Also a lady’s man. Janice was fascinated by how confident and proud he was, and how he didn’t bother to disguise himself (she was forced by her family to always cover her inhuman traits with clothes). They got together, he kicked her primary suitor’s butt in front of everyone, and they eloped, becoming even more crazy together.
TLDR: Tiefling Bonnie and Clyde, but just plain crazy, and much more destructive.
While some of my friends are making 3/5 of our party siblings in my upcoming game, I have some better but older stories on this.
1. Playing a CE character who had convinced a LG character that the LG character was their guardian and needed to be with them. This had apparently led to "6 years of therapy" at one point. The CE character was 10.
2. One time my character worked for a vampire and another was playing their 'I hate you dad' dhampir son. I was a half-faerie dragon.
And I think the one that takes the cake:
3. Snowball game. So backwards time 'scenes' - you start at end, do a bit, then go to previous scene. Characters start with one defining trait that they get bonus dice from, but develop more as the scenes go backwards in time. And rolls are done with nd6 , any 1 gives you a victory that YOU narrate, any 6 with no 1's gives a defeat that YOU narrate, and no ones or sixes and the GM decides what happens. I mention these rules because I shamelessly abused them.
We were playing a sci-fi oneshot. I decided my defining trait was 'Eldritch Puppetmaster'. The other players had more typical traits, like 'swordmaster', 'air blades' 'electrity powers' and a few others that I forget.
I described 'Eldritch Puppetmaster' as being it in all senses of the phrase. My character was eldritch and puppetmastered those around him. He puppetmastered eldritch horrors. I also said that long ago he put on puppet shows for children called 'My Little Cthulhu'.
...And as the game progressed, I also ended up puppetmastering all the other players. You see, the rule stating that 1's lead to successes and 6's losses, but the player gets to decide ended up letting me convince the other players, usually with a 'wouldn't it be awesome' or 'what if' to basically to give their defeats to me. I ended up the antagonist of the rest of the party, but basically got way more 'successes' as every loss from the others I convinced them to help me. Things like instead of failing to save a girl, they did end up saving the girl but she immediately turned into an eldritch horror.
But anyway, to the backstory part.
I had set myself up as the villain, sneaked aboard their escape pod as a lone tentacle in the first scene, 'died' in our second scene, and subtly worked against them in the further scenes. Between scenes we were allowed to try to roll for adding a new trait to our characters...
So the swordmaster said that maybe we had been friends before, and worked together in the Knights Templar, but I had betrayed them.
He rolled and got a failure that he could describe.
Him: "Hmmm...I guess we weren't friends?"
Me: "Or...I wasn't the one who betrayed them."
So that is how the Knights Templar turned out to be a Cthulhu Cult.