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When he was six, he met Clary Fray and the pair became inseparable best friends.
He soon developed romantic feelings for her and pined for her for the next ten years without voicing affections.
The day after the Pandemonium Club incident; while at Java Jones, listening to Eric's poetry reading, Simon was just about to tell Clary about his feelings for her, when at that moment, Clary left to confront Jace, the Shadowhunter she met at the Pandemonium Club, whom Simon couldn't see.
Simon did not see her until three days later, when Simon was hiding in Luke's backyard and was apprehended by Jace, thinking he was an intruder.
After drinking a blue drink, while with Isabelle, Simon turned into a rat and was taken by a vampire, thinking he was one of theirs.
Jace and Clary broke into the vampire's lair, Hotel Dumort, to save Simon.
And I see on your face when you're looking at me that you're searching for that guy. A mundane when they were originally introduced to the Shadow World, Simon was once turned into a vampire, and later to a Daylighter.
When Clary's mother disappeared and the Shadowhunters finally revealed themselves, both were thrown into the strange Shadow World.While fighting with the vampires, the Werewolves also broke into the hotel looking for Clary.During the raid to save him from the vampires, Simon bit Raphael Santiago, a vampire, unwillingly making him a fledgling.Over dinner Simon also met Hodge Starkweather and Alec Lightwood.The next morning, after Clary and Jace met with the Silent Brothers, the gang met for breakfast at Taki's, including Simon who had shown up at the Institute.