Toby Cavanaugh

Toby Cavanaugh is Jenna's older step-brother. Alison and her friends believed that Toby used to spy from his tree house window into Alison's window. One time, Alison and her friends tried to get revenge at Toby, but ended up blinding his stepsister, Jenna Marshall. The girls refer to the incident as "The Jenna Thing". Toby ended up taking the blame because Alison saw him doing something sexual with Jenna (later revealed as forced) and didn't want her telling anyone. Later he becomes Emily's lab partner. Spencer, Hanna and Aria are worried that he will hurt her when he takes her to homecoming. Eventually, they come to believe in his innocence in Alison's murder, and Spencer even dates Toby. Toby has a tattoo commemorating September 1, the day he ended his relationship with Jenna. In earlier episodes, Toby had been one of the suspects to be "A".

Season 1
In To Kill a Mocking Girl, Toby reappears at Rosewood High after a mysterious, yearlong absence – leaving the girls to wonder whether he had anything to do with Alison’s disappearance, or if he is "A."

In the next episode, Toby becomes Emily's lab partner, much to Emily's dismay. Toby notices when Emily slams her lab book shut, though he doesn't know that it is because of the photos planted there.

Eventually, Emily and Toby start becoming friends. Their surprising friendship grows even stronger when Toby decides to make Emily a mix tape, complete with a comic book-like sketch of Emily, much to the dismay of a suspicious Jenna.

Emily and Toby schedule to meet, but when Emily arrives at the cafe, she sees Spencer and Hanna. Too embarrassed to socialize with Toby in front of them, she reluctantly blows him off. Later, the waitress hands Emily the mixed CD Toby has left for her, leaving Hanna to believe Maya made it for her and encourages Emily not to bullied by pursuing a nonconventional relationship. However, Emily takes the hint regarding toby. Later the next day, an upset Toby tries to ignore Emily when she comes to sit with him, but gives in when she presents him with a mixed CD of her own.

In There's No Place Like Homecoming, Toby surprises Emily with tickets to the dance. She’s nervous to accept because of what her friends may think, but is starting to like him.

Later, the PLL's discover Toby’s tattoo – "9/01, Free at Last", presumably memorializing the date Alison disappeared. At the dance, the PLL's are anxious that Emily is not safe with Toby. Then, Toby whisks Emily away to the Chem Lab to confide in her privately about his big secret, which the girls have just uncovered in what turns out to be Toby's file that Hanna retrieved from the psychiatrist, not Jenna’s. They send Emily a text message claiming that Toby killed Alison, making her more and more unsettled. As Toby tries to explain, she pushes him into the cabinet of beakers, injuring him badly before hurting herself as she runs away and trips on the train of her dress, hitting the hard floor and falling unconscious. At the end of the episode, Toby is dropping an unconscious Emily off at the emergency room and driving away.

When Emily gets back from the hospital, Aria, Hanna and Spencer mistake Emily’s wounds for an attack by Toby, and quickly inform her of his sordid past with stepsister Jenna to keep her from contacting him again. Later, Jenna visits Emily asking her to bring her Toby's file. The girls, sans Emily, head toward the shed to hide Toby’s file that Hanna stole, but in a panic, Aria decides to throw it in the river instead, and it seems "A" picks it up instead.

A day later, Emily discovers cops in front of the Cavanaugh house, with a shaken Jenna in tears – just as she receives a text from "A": "Thanks for getting Toby out of my way." She sees a smashed up motorcycle, but is too afraid to ask if Toby is alive.

In "Monsters in the End", Spencer and Toby engage in a kiss in front of her mother and her sister.

Season 2
In "It's Alive", Spencer's father keeps Toby from seeing Spencer, but Toby later returns at her house at night, scaring Spencer by not knocking on the door to the point of her brandishing a buthcher's knife, but Toby had only been trying to avoid alerting the rest of her family to his presence. He stays, and the two talk for a while. When he leaves he tells Spencer to "lock the doors." Spencer responds with " Yes sir." as she watches him leave.

In "The Goodbye Look", Toby shows up at school and tells Spencer he is going to get a GED and that he has a job at a construction company. Spencer sits in her car and watches what appears to be Toby being laid-off. He walks over and says the customer saw him and told them they'd fire the company if he wasn't removed. The construction boss did pay Toby the week's salary anyway. That night, Toby comes to Spencer's house asking to hang out.

In "My Name Is Trouble," Toby comes to the school to drop off his GED paperwork and he tells Spencer he has another construction job with Jason. Spencer doesn't really like that, but she makes him promise he won't go inside Jason's house because she doesn't trust Jason. He says " promise" and kisses her. Spencer comes to visit Toby at work and tries to get him to quit when Jason goes in the house to get a drink, but he tells her he needs the money. Spencer finds the engagement ring that Melissa had been looking for and she sells it to a pawn shop. She uses the money from the pawn shop to get Toby the truck he wanted. Toby responds by saying "I love you so much", to which Spencer replies "I wanted to say that first". The two then kiss.

In "Never Letting Go", Toby walks Spencer home. The two can't keep their hands off each other. The two even make out in the Hastings doorway. Spencer to Toby "Wow you sure know how to walk a girl home." Toby to Spencer(while kissing her face and neck) "So what time do you need me tomorrow?" Spencer to Toby "After schoolish you know after the meeting,you think you can build me some makeup tables?" Toby to Spencer "For you I'll won't sleep until it's done." The two kiss again then say goodnight.

Later at the fashion Spencer goes backstage to talk to Toby while he makes the makeup tables. Spencer to Toby "Mona is five feet of insidious snark with a side ponytail and I just want to grab and yank it really really hard." Toby to Spencer "Spence, she stepped up while you dealt with some pretty big things, things that were way out of your control, but look maybe we should just both enjoy the fact those pretty big things are over,we can both take a breath." Spencer to Toby "Yeah your right." The two then giggling and kiss again.

Later on in the fashion show while Spencer is giving out swag bags Toby comes talk to her. Toby to Spencer "You look amazing", Spencer to Toby "Thank You" and then kisses him on the cheek. Out of nowhere incomes Mona, Mona to Spencer "Where's your headset here just take mine, I need you to track down the tribute slide show disc and give it to Noel okay" Mona then walks away leaving Spencer pretty stunned and angry, Spencer to Toby "I wanna" Toby interrupts her "take a breath."

Emily Fields
Toby and Emily appear to have feelings for each other at the beginning of season one. At first Emily is unhappy that Toby is chosen to be her chemistry lab partner, but then she warms up to him, eventually accepting his request to attend homecoming together. When Toby realizes Emily is gay and in love with Maya, he backs off, and the two remain close friends.

Spencer Hastings
Toby and Spencer look like they may be moving beyond friends in the next few episodes to come. Toby is helping Spencer catch Alison's killer so he won't be framed again. Toby and Spencer kissed at the end of "A Person of Interest" after she leaves the motel bedroom. They also engage in flirtation throughout the night in the motel room including sharing a bed while Toby is shirtless.

Trivia

 * Credited as Toby Marshall in the "Pilot".
 * Along with Ian Thomas, Jessica DiLaurentis and Jason DiLaurentis, he is one of the only characters to be played by different actors/actresses by the Season.