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Story[]

Season 4[]

"The Kids Rob a Train"[]

Sylvester Stieblitz first appears in "The Kids Rob a Train," where he appears with a woman called Mandy, whom he made contact with on his E-Kiss (an online dating site) profile. He takes her on the Wine Train where it is later revealed that he had lied on his profile including his photo and failing to mention he had a son. He and Mandy later make up after a wine fight.

Season 6[]

"House of 1000 Bounces"[]

Sylvester next appears in "House of 1000 Bounces," where he is in charge of his son's birthday party. Louise Belcher suggests he goes after Sasha's aunt, Caitlin, as a distraction for the kids to steal the bounce house from Dahlia's party, which he does. After the heist, Caitlin doesn't show any interest in swapping numbers.

Season 9[]

"Better Off Sled"[]

In "Better Off Sled", Rudy says that he now has a friend called Nancy.

Season 14[]

"The Amazing Rudy"[]

In "The Amazing Rudy", his new girlfriend is a woman named Vicky. It's implied they haven't been dating long, but it's serious. She is the first of Sylvester's girlfriends to be invited to monthly "We're Still a Family" dinner with Rudy and his parents (along with his mother's boyfriend Paul).

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