The two of them grew exceptionally close from Season 5 and beyond. Their friendship was particularly a result of a mutual bond with the late J.T. Yorke, Toby's best friend and the love of Liberty's life. When J.T. was murdered by Drake Lempkey in season six, Toby and Liberty briefly found romantic comfort in each other to cope with the pain of their loss. While Toby's feelings for Liberty were sincere, she was simply emotionally vulnerable after J.T.'s death, so a relationship between Toby and Liberty never became official. Toby felt rejected by Liberty again when she chose to pursue a very short-lived romance with Damian Hayes instead of him. Nonetheless, Toby and Liberty remained good friends.
In Jagged Little Pill, Liberty and Toby, along with several others, attend Ashley's disastrous party at the end of the year.
In Girls Just Wanna Have Fun, Toby and Liberty are seen at the 80's dance together.
In It's Raining Men, Toby and Liberty go to J.T.'s party.
In Ghost in the Machine (1), Emma, Toby, and Liberty are seen walking to school together.
In The Lexicon of Love (1), Toby and Liberty attend the premiere of Jay and Silent Bob Go Canadian, Eh! together and sit next to one another. After the movie, they both attempt to get into the VIP party, though the bouncer doesn't let them through.
In Together Forever, Toby and Liberty are leading a student council meeting, and they close off the meeting. Toby suggests to Liberty that J.T. should give Liberty a ride to the assembly, but she rejects the idea, saying she doesn't talk to him. Toby questions how the baby is, and Liberty answers that her doctor told her to take it easy, as he thinks she is overstressed. Toby tells her he is there to help her with anything. It is revealed Toby has been telling J.T. status updates about Liberty's pregnancy behind her back.
While Toby and Liberty are discussing a meeting, Principal Hatzilakos walks in and tells Liberty that Toby should go alone to the assembly, so that Liberty would be able to rest. Liberty asks Toby if he talked to her, which he denies, though he suspiciously lies and escapes from the situation. Liberty later confronts Toby about telling J.T. about her pregnancy, who therefore told Mrs. Hatzilakos. Toby lies and says he is the one who told her, and Liberty insists on coming to the assembly, ignoring Toby's advice to listen to her doctor. Later, on the way to the assembly, Toby's car dies, and Liberty goes into labor, leading Toby to freak out. They call 911, and Liberty is loaded onto the stretcher to be taken to the hospital, while Toby is left to go to the assembly alone. However, Toby is shown at the hospital with Liberty while she is holding her newborn son in her arms, and tells Liberty that the adoption counselor is in the hall.
In True Colours, Emma, Liberty, and Toby discuss a theme for the school's dance.
In Here Comes Your Man (1), Toby, Liberty, and J.T. are walking together on the first day of their senior year of high school. Liberty remarks that this year will be the crowning achievement of her academic career, and Toby comments that he can already hear her valedictorian speech.
In What's It Feel Like To Be a Ghost? (1), Toby and Liberty are sitting together at The Dot when Mia Jones enters. As Liberty is jealous of Mia's relationship with J.T., she unleashes the bombshell on Mia that her and J.T. had a child together, and J.T. sold drugs to support them. Upon this realization that J.T. told her none of this, Mia storms out, and Toby comments, "Ouch", as she leaves. Later, at a student council meeting, J.T. and Mia are pitching the idea to build a daycare in Degrassi, and Liberty is refusing to talk about the idea. J.T. urges Toby to back him up, so Toby mentions that maybe Liberty should let J.T. finish his pitch. She gives him a look and he quickly states, "Or not".In The Bitterest Pill, Toby attempts to help Liberty feel better about J.T.'s death. At his funeral, they discuss how J.T. would prefer having whoopee cushions on every seat to having people, like Mia, crying their eyes out over him. Toby tells Liberty that he wants to build J.T. a memorial, and specifically asks for her help. Liberty later confesses to him that she can't feel a thing, and Toby tells her that they are going to get through this together. She questions why he is being so nice to her, and Toby responds that he knows how hard this must be for her, so he wants to be supportive, though he still avoids telling her that J.T. returned her feelings.
Mia, Toby, and Liberty are later cleaning out J.T.'s locker. Mia becomes angry with the two of them when they don't want to go along with her idea of playing the tape of J.T. playing with her daughter, Isabella, at the memorial. She and Liberty get into a fight, which causes Liberty to storm out, with Toby chasing after her. He suggests that the two of them go on a road trip to get away from everything at Degrassi. The two cut class to go on the trip, but Toby's car breaks down in the middle of the road. He gets out of the car to curse and kick it, which causes Liberty to laugh. Toby is glad he didn't fail in cheering her up, and the two lean in for a kiss, though Liberty pulls away, looking confused.The next day, Liberty greets Toby, and Toby denies to Danny that there is anything going on between him and Liberty to save himself from getting beaten up. Manny oversees this, which leads to her getting Toby to admit that he kissed Liberty the day before, and she makes him promise to take the kiss back. However, when he tries to do this with Liberty, she says the problem is solved since they both like each other. Later, Liberty overhears Toby telling Mia that J.T. still had feelings for Liberty, which left her feelings completely betrayed. Toby feebly tries to say that he tried to protect her by not telling her, but she leaves him, forever crushing any chance at a relationship.
In Don't You Want Me? (2), the two talk at the dance about how J.T. never would have let Toby live it down that he was crowned "Ice King".
In Standing In The Dark (1), Liberty and Toby eat lunch on the steps of the cafeteria because there is nowhere to sit inside. Toby is angry that "J.T.'s killers" are here, but Liberty logically tells him that one person killed J.T., not the school. Later, Liberty confronts Toby about his podcast that declared that Lakehurst wasn't welcome at Degrassi, and asks him if he wants an ongoing war.
In Another Brick in the Wall, Toby is seen sitting next to Liberty outside. When Holly J. tells Toby that she got a good grade thanks to his tutoring, she asks Liberty for some space, who had been standing next to Toby. Toby later turns down Holly J., as being with her would impress all the people he didn't care about, which prompts Holly J. to ask, "You mean Liberty?".
In Don't Stop Believin', Liberty is angry that she and Damian Hayes are tied for valedictorian, and comments to Toby that it is "so unjust", as he has only been there for one semester. Later, Toby films Liberty's video, but does not approve of her mudslinging strategy. When the videos are being watched in class, Damian was polite in his, while it would make Liberty took bad since she badmouthed him in her video. She pretends to choke, and Toby tries to give her the Heimlich maneuver, though Liberty punches him away with her arm. When the power conveniently goes out before Liberty's video can play, Toby records Liberty speaking her video about Damian to the class instead. The next day at lunch, Liberty is announced valedictorian, and Toby points out if it weren't for the blackout, the podcast, or the choking fit, Liberty would not have gotten the position. Liberty acknowledges to him that she did get lucky.In We Built This City, Toby tells Liberty that Ms. Hatzilakos approved it so that after graduation him, Liberty, Emma, and Manny could mourn J.T. at his memorial. Toby asks Liberty to prom as his date, and she accepts, though makes it clear that they're only going as friends. Manny, Liberty, and Emma have an all girls + Toby hug before the prom when they realize they're all going their separate ways soon. When Natasha Bedingfield toasts to Liberty, Toby gives her a side hug. Later, while dancing with Toby, Liberty asks Toby what to do about her feelings for Damian, and Toby is angry that she was thinking of Damian while on a date with him, revealing she still only thinks of Toby as friends, even though he felt the prom date meant more. Later, Liberty confesses to Toby that she followed her heart with Damian, but when Damian starts bragging about their hook-up to Toby, he reveals it to everyone. Manny, Liberty, and Toby do not forgive Liberty until she breaks down crying in her graduation speech about how special friends are for the journey together. They all reconcile, and place a graduation hat by J.T.'s memorial at the schools.
In Toby Dynamite, Toby performs his dance for Liberty's student council president campaign.
In Six Months, Toby comforts Liberty for the 6 month anniversary of J.T.'s death. The two and their other friends mourn for him.
In Party Etiquette, Toby is trying to hide from both Liberty and Holly J. Holly J. finds him and drags him into a bedroom to have a "secret thing", before Liberty opens the door on the two of them. She tells Holly J. that her and Toby kind of have a "secret thing", and both girls resort to finding and hurting Toby after they think he has led both of them on.
In Back to Degrassi, Toby creates a time machine for Liberty, so that she could get Emma to go back in the past and prevent J.T. Yorke's murder. The two overlook Emma as she performs the mission.
- Emma: "Chris and I broke up in July."
Toby: "Sorry. Kendra and I broke up in August."
Liberty: "Sorry. I believe I was abducted by aliens over Labor Day weekend...And Towerz and I broke up."
Emma and Toby: "Sorry." - Ghost in the Machine (1)
- Both wear glasses.
- Both only had brief appearances after they departed: Liberty at Spinner and Emma's wedding and Toby at the Niners' Robot Wars.
- They are both intelligent and were the closest to J.T.
- They grew closer after J.T.'s death.
- Both used to be in the "loser" crowd.
- Both were friends with J.T. Yorke, Manny Santos, and Emma Nelson.
- They have kissed.
- They both graduated in the Class of 2007.
- They were seen in the Season 3, 4, and 5 opening credits together.
- They both made their first appearances in Season 1: Toby in Mother and Child Reunion (1) and Liberty in Family Politics.
- They were both members of the Degrassi Drama Department and the Degrassi Student Council.
- They both attended J.T.'s funeral and memorial service at Degrassi in The Bitterest Pill.
- They were each other's prom date.
- Liberty disliked Toby's friend Holly J. Sinclair.
- They both appeared in Kevin Smith's film Jay and Silent Bob Go Canadian, Eh!.
- They were both members of the Rooks & Knights Society.
- Liberty was friends with Toby's stepsister Ashley Kerwin. Both she and Liberty served as Student Council President.
- Start Up: The Bitterest Pill (612)
- Broke Up: The Bitterest Pill (612)
- Reason: He didn't tell her that J.T. was still in love with her when he died.