|This article centers around Toby Cavanaugh, a book character. For another version check out Toby Cavanaugh, a TV character.|
|“||Seeing all those people tonight just made me realize how hard it used to be, living in Rosewood.||”|
— Toby Cavanaugh
Toby Cavanaugh was Jenna's older step-brother. Toby took Emily to the Foxy Benefit Dance, but Emily thought that Toby was "A" and Alison's killer, and she wanted to get away from him as soon as possible. They talked about his "secret" to which they both were talking about something different, but they didn't know it. Later, Toby couldn't take it anymore because coming back to Rosewood was too painful for him, so he ran into the woods and commited suicide by drug overdose.
Toby is tall, pale, and lanky. He has dark brown hair, blue eyes, and high cheekbones.
One year older than his stepsister, Toby had a bad reputation in middle school. He was rather creepy and perverted, resulting in a flurry of outlandish rumors about him being spread around Rosewood Day. Although his parents didn't like it, Toby constantly set off fireworks, and was eventually told that if he set any more off, they would send him to a boarding school in Maine.
One night, when sixth graders "Alison" DiLaurentis, Spencer Hastings, Aria Montgomery, Hanna Marin, and Emily Fields were having a sleepover, Toby spied on the girls changing clothes. They screamed when they saw him and he only smirked in response. While they expressed their outrage, he ran off to his tree house and started to sexually abuse Jenna. While assaulting his stepsister, Toby noticed movement in the Cavanaugh yard and saw Ali staring up at them with a firework in her hands. The firework hit the tree house and Jenna was blinded as a result. Toby was infuriated by what he just saw and walked over to Ali's yard, telling her that he saw her and planned to tell the police. However, Ali has discovered his perverted actions towards Jenna and blackmails him into taking the blame. As a result, Toby is sent to a boarding school in Maine.
Three years after Ali's disappearance, Toby returns to Rosewood. He is no longer the creepy looking boy everyone avoided, and he has grown into his looks and is rather handsome in a brooding way. He attended Tate Prep School, another private high school in Rosewood, and is part of the swimming team. He meets Emily again when he stops her ex-boyfriend Ben from sexually assaulting her. He helps her again when she faints and gives her a ride home. She screams when she wakes up in Toby's car but he manages to calm her down and the two have a chat about what they've been doing and he seems to have changed for the better in Emily's opinion. They meet again at the Rosewood-Tate swim meet and kiss before starting the competition. The photographer takes a picture of her "flirting with the enemy" Toby takes her to the Foxy benefit dance and all seems to be going well. They decide to leave the dance after a while and use Toby's car to travel.
However, the good mood is shattered when Emily talks about her sexuality and mentions Alison. Toby says that he hated Alison and is glad that she finally got what she deserved. Emily is horrified by this and begins to think that Toby killed her. She jumps out of the car and runs away from him, but he follows her to her home where she tells him she knows his secret. Toby misinterprets her and thinks she knows about his situation with Jenna. He tries to explain that he is ashamed of it and wishes he'd never done it, but Emily thinks he is talking about Alison and is disgusted. He begs her not to tell anyone as he has finally gotten his life on track, but she refuses and tells him to go away. Toby does and runs into the woods behind Emily's house, where he overdoses on pills, which results in a fatal death. The next morning, his body is found.
"I saw you. I'm going to tell."- Toby's confrontation with Alison DiLaurentis.
"Are you happy to be in Rosewood?"- Toby (his sarcastic response to Emily's question about returning to his hometown.)
"People used to really hate me. But tonight, everyone was so nice- all these people who used to make fun of me. It was sickening, It was like it never happened."
"You guys were such a clique back then. You really let people have it. Me...my sister..."
"I know you were friends and you loved her and whatever, but personally, I'm glad that bitch is dead."
"But, Emily, you don't understand. I was so young. And...and confused. I wish I hadn't done it..."