Toby comes to the Hastings' house to check on Spencer. Her father prevents him from coming in and talking to Spencer telling him that she can't afford to be seen with him because of his reputation. Toby and Spencer plan a secret meeting with the help of Emily. Toby is in Emily's room waiting for her as she tells him about her moving to Texas. After Spencer texts her saying she can't make it, Emily says she is sorry and Toby says it's okay. Emily also says she is sorry for believing he killed Ali, and the two rekindle their friendship because Emily says she feels like she is leaving four friends, meaning Spencer, Hanna, Toby and Aria.
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 let go. He walks over and says the homeowner saw him and told them they'd fire the company if he wasn't removed. The construction boss paid Toby the week's salary anyway. That night, Toby comes to Spencer's house asking to hang out. They drive to the Hills overlooking Rosewood. They sit on a rock looking at Rosewood. Spencer asks if she wants him to go to the police, but he says they don't do either of them any good. He pulls her in and she calms down on his shoulder.
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, and makes him promise he won't go inside Jason's house because she doesn't trust Jason. He promises 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. He would get a job out of town if he had transportation, but he can't afford it. Spencer buys Toby the used truck he had his eye on. They confess their love for each other and kiss.
At the fashion show, Spencer goes backstage to talk to Toby while he builds the makeup tables. She expresses her frustration with Mona and how she wants to grab her ponytail and yank it really hard. Toby clams her down by saying that Mona had stepped up with she had dealt with so things in her life and that they couldn't control them. He says that those things are over now and they can both take a breath. This does calm Spencer down and they kiss. Later on, while Spencer is giving out swag bags, Toby comes talk to her and compliment her. She thanks him and kisses him on the cheek. Out of nowhere, in walks Mona, who starts barking orders at Spencer. Spencer begins to say something but Toby talks her down and Spencer takes a breath.
Spencer's dad hires Toby to build the nursery for Melissa's baby. Spencer finds him working and begins to flirt with him until her dad comes. Toby shows him some plans he had came up with and Peter seems to like them. Spencer smiles at this because her parents are starting to like Toby. After her dad leaves, Spencer and Toby kiss. While working in the yard, Toby makes a major find in Spencer's backyard - a broken field hockey stick. Toby asks why it was buried but Mr. Hastings doesn't say anything and leaves. After he tells Spencer about finding it and the way her father reacts to it, Spencer thinks that the hockey stick may have been what killed Alison. Toby comforts Spencer when they meet on the outskirts of Rosewood, and she says that her father believes the possible murder weapon was a prop set up by her much like how Ian's trophy was.
He comes back to help Spencer go through Ian's things. He discovers that Ian was part of the N.A.T. Club. Spencer, who never heard of the club looks through the yearbook to find that Jason and Garrett were part of the same club. Later, Toby and Spencer see Aria and Jason at The Grille. Toby suggests she go inside to talk to Aria, but Spencer knows Aria won't want to listen to what she has to say.
Toby drops Spencer off at school, where she is nervous that Jenna has joined the N.A.T Club. Toby says he can try to find information about it from Jenna, but Spencer says he shouldn't and that it would give Jenna an even stronger motive to break the two up. Toby assures her that it would never happen and kisses her. The two are making out in Toby's truck, when he sees a shadow in Jason's house. Toby decides it was probably nothing and the two continue to make out but Spencer now sees two shadows. Spencer and Toby get out of the car and Spencer storms up to the door, but is in shock when her dad comes out of Jason's house. When her dad says that he doesn't have to answer to her, Toby steps in an says that he owes Spencer answers. Spencer acts as a barrier between the two when her dad goes at Toby, and she runs away, making her dad charge at Toby's truck.
Toby is at Spencer's house. Apparently, his truck wound up at the mechanic after the brakes stopped working, which alarms Spencer, considering he treats it like his baby. He says that the brake line was cut, and that it probably happened at work. Toby then asks Spencer if her dad gave her an answer to why he was there that day. She says that he wouldn't tell her, and that she left it at that. Toby then says that she's not the type of person who would easily leave things alone, which leads her to say that he doesn't know her father as well, and to give it a rest. Later, the two are sitting in Toby's truck, and Spencer admits she lied earlier. He says that he thought they trusted each other. Spencer then says that she can never tell him everything that really happened, which pushes her to tears, as she says that he deserves someone who can be completely honest with him. Before he can say anything, she runs away.
Emily spots Toby unloading a moving van on her way home. Emily approaches him and notes his subdued mood as he fingers a snow globe. He's bummed that his dad has remarried and that the new wife is moving in with her daughter. Emily asks what the daughter is like, and he responds eerily that she gets whatever she wants.
Through Many Dangers, Toils, and Snares
At the Rosewood-Rollins swim meet, Toby tries to get from Emily why Spencer is acting so strangely, but knowing that "A" is probably watching her, Emily tells him that they are still not speaking. Toby tells her that she doesn't want this to ruin their friendship, and Emily tells him it's not a good time for anyone. After the meet, Toby watches the fight between Spencer, Aria, and Hanna and Emily. Later at Spencer's house, Toby tells her that even if they don't get back together, he doesn't want to see Emily and Spencer fight considering he cares about them both. Spencer then tries to walk away, saying, "What do I have to do to get you to leave me alone?" Toby then startles her by saying that she's starting to act like Alison did when she was still alive. Spencer says she can't give him answers now, but things will be different by tomorrow. She makes him promise that he won't follow her when she leaves.
Spencer comes over Toby's house who still seems sullen, but allows Spencer to talk to him. After Spencer says that shutting him out is killing her, Toby asks, "So you came here to tell me that you can't be here?" They exchange a smile and Toby pulls Spencer in for a kiss. Soon they see Garrett arguing on the phone with Jenna. Toby tells her that their arguing started the night before. When Garrett looks over into Toby's car, Spencer quickly ducks, but Toby remains there, making direct eye contact, showing he is not afraid. Later, Garrett comes over to the Cavanaughs' house, and Toby is standing there watching him. Garrett asks if anyone was with Jenna when she left, but Toby gives him a somewhat ambiguous answer, only shrugging. Toby also shows how he still resents Jenna, saying that "maybe she likes [it better in Rosewood], settling scores." Garrett seems especially annoyed by this, saying that Jenna is a strong person, and Toby responds by saying, "I never questioned her strength. Only how she uses it."
He goes to the Hastings' house to pick up some things that he had left. The scaffolding gives away and Toby falls, breaking his arm. Off-screen, Mrs. Hastings finds him and gets him to the hospital. At the hospital, Wren introduces himself as Toby's doctor. Still unaware that Wren and Spencer had a relationship, Toby suspects that something strange is happening between the two of them. Wren checks up on Toby later, and asks if he can get Toby anything. Toby asks for some answers. Wren, clearly stunned when Toby brings up Spencer, says that when he kissed Spencer, he thought they were over. After Wren says that, Toby says, "I'm just saying, I may have broken my left arm, but my right arm's fine." As Toby is getting ready to go home, he looks back and sees Wren, upset about what happened between him and Spencer. At his house, the girls find that he's gone.
Toby comes back with a new haircut and a brand new attitude. Spencer sees him in school and they have a very awkward conversation about Jenna. When Spencer says that he is back to guiding her around he defends Jenna and tells her to get used to it. When Spencer brings up their relationship he says that it is too late. Jenna comes out and her and Toby leave. At the hospital, Toby sees Wren. Wren and Toby talk about his broken arm and how he was out of town and saw another doctor. After Wren leaves, Toby still looks angry and Jenna makes a comment about how he is Spencer's personal physician. Hanna tells Toby that he can't let Jenna back into his life again. Toby tells her to shut up and assures her that she doesn't know what he is doing or why. After the fire, Toby is with Jenna when she wakes up and he tells her that Hanna had pulled her out of the fire. Toby then goes and finds Spencer and tell her that Jenna wants to talk to all of them. He then asks her if she is okay which proves that he still cares about her.
Toby checks on Jenna when she is taking off her bandages. He wants her to wait for the doctors but she takes them off anyway. When Jenna begins to cry because she supposedly can't see, Toby says he is sorry. He then takes Jenna to school where she wants to talk to Spencer, Hanna, Emily and Aria. He drops Jenna off while glaring at Spencer. The next night, Toby goes in Jenna's room wanting to know why Garrett is stalking their house. Jenna gives Toby page 5 of Ali's autopsy report and says that Garrett gave it to her. Off-screen, Toby gives the page to the police and Garrett is later arrested for Ali's murder.
Spencer sees Toby doing yard work in Jason's house. When she asks if he'll ever be able to forgive her he says he has work. As Spencer leaves she begins to cry and says he has a right to be mad at her, but also that he doesn't have to be that guy who shuts everyone out. After Spencer gets back in her car, Toby gets a call from Dr. Sullivan. After Spencer and her friends find out who "A" is and they leave the place where Mona is, Dr. Sullivan says that their friend helped her come back to Rosewood and face her fears. After Spencer inquires what friend she's talking about, she sees Toby waiting near his truck. Realizing he is the "friend," they walk up to each other and Toby says that "Pretending not to love you was the hardest thing I've ever had to do." She goes to slap him, but he grabs her and pulls her in for a kiss with the Liars and Dr. Sullivan looking on.