We have Team Rocket's Jessie of the Pokemon franchise being bound and gagged in her birthday suit.
In Crossing Paths, it was revealed that she had a crush on a boy she had gone to school with named Astin, who has a current-day counterpart with a similar name.
When she was old enough, she left home to become a Pokémon nurse. However, she was unable to go to a regular nursing school and went to the Pokemon Nurse School, which was intended for Chansey. She was quite skilled at things such as bandaging, and even showed a Chansey how to do it, which she quickly became good friends with. However, because she was not a Chansey, Jessie couldn't do things like use Sing to soothe Pokémon, instead falling asleep herself. Ultimately she failed to graduate, and on graduation day she simply packed a bag and left. As she was leaving, Chansey came up to her and offered her her nurses' hat, but Jessie refused to take it. Chansey then broke her egg-shaped pendant she got as proof of graduating in half and gave one half to Jessie so that they would have something to remember each other by. In the episode Ignorance is Blissey, Jessie was reunited with that same Chansey, which had since evolved into a Blissey.
It is assumed that she then enrolled in Pokemon Tech, a Trainers' school, where she met James, and subsequently failed and dropped out. After this, as revealed in The Brisge Bike Gang, Jessie and James joined a bicycle gang in Sunnytown, where Jessie was known for swinging a chain above her head as she rode her bike, acquiring the nicknames "Big Jess" and "Chainer Jessie".
It was revealed in Spring Fever that she was supposedly a model at one point.
Sometime before joining Team Rocket, and it is not known when, Jessie obtained a Contest Pass in the Hoenn region. Also during the years before Team Rocket, she had several boyfriends, all of whom left her and/or treated her badly. In Xatu the Future, she revealed that she had once worked at a TV station as the weathergirl. In From Cradle to Save, it was revealed that she once was a ninja.
Due to conflicts in canon between Kanto and Johto episodes and the special episode Training Daze, what happened between Jessie and James after the bike gang is unknown. What is known, as shown in the special episode, is that they joined Team Rocket separately and were on initially unfriendly terms after being grouped withMeowth but they quickly made up and became good friends.
Team Rocket member Wendy held a grudge against Jessie for failing to pay for a drink (making Wendy pay), but got her revenge when she added the charge to Jessie's overall Team Rocket bill. (However, Jessie revealed to Meowth and James later on that she didn't even like fruit smoothies for some reason.)
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