[HEADCANON #1]

Tim has a secret love for country music but he won't admit it because he always teases Jay about being "too country" and doesn't want to be seen as a hypocrite

[HEADCANON #2]

Tim's Schizophrenia causes him to have intense dreams of his bones snapping one by one
This wakes him up every time and is a huge contributor to his insomnia

[HEADCANON #3]

Tim has been arrested more than any other Proxy

[HEADCANON #4]

Tim's dream job would have been to be a contractor
He was very good at electrical, lumber, concrete, and everything else needed

[HEADCANON #5]

Tim dropped out of high school in his Junior year to work full time

[HEADCANON #6]

Tim started smoking at the age of 12

(Credit to georgeroni)

[HEADCANON #7]

Tim started avidly taking pills when he was 15

[HEADCANON #8]

Tim was the breadwinner between him and his dad and he had to work multiple jobs to be able to pay their living expenses