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Throughout the series, outside forces threaten those he loves and the life he most desires to have: a normal, human one.In Season Five, Stefan was killed by Julian in Promised Land while trying to protect Caroline, but he was resurrected one episode later in Home due to Damon's sacrifice to save him, and this caused him great anguish.Giuseppe, hearing Katherine collapse, entered and set in motion Katherine's capture.
After the ball, Stefan walked Katherine up to her room and confessed his love to her.
During this conversation, his father drugged him with vervain.
When Katherine went to see Stefan that night and bit him, the vervain poisoned and incapacitated her.
In the 1920s, Stefan had a brotherly friendship with Klaus and was romantically involved with Rebekah Mikaelson.
He was best friends with Lexi Branson until her death, and Caroline Forbes.
To calm him down, Katherine compelled him to not be afraid of her.