Holly J. and Toby met outside the cafeteria in Standing in the Dark (1). During a rant to Liberty Van Zandt about how Lakehurst Secondary School's students should not be allowed at Degrassi (given the death of J.T. Yorke at the hands of the Lakehurst student Drake Lempkey), Toby swung his arm through the air, hitting Holly J. as she and Anya MacPherson were leaving the cafeteria. Holly J. snidely asked him whether he was trying to feel her up, and walks off with Anya trailing behind her.
In Another Brick in the Wall, Holly J. found out that she was failing math class, and needed to pull her grades up. Meanwhile, she secretly resented being single, as her best friend Anya and even her rival Mia Jones had boyfriends.
Having been told by her older sister, Heather, that Toby's math skills would make him a good tutor, Holly J. sought out his help. Toby was reluctant to tutor her, as her mean girl reputation preceded her. Nonetheless, he agreed to help her if she helped him pass PE class.After Toby helped Holly J. with her math work, Holly J. met him in an empty classroom to tutor him in the video game, Dance Dance Revolution. She was amused but charmed by Toby's lack of rhythm, and got behind him to guide him. Toby tripped, and the two fell to the floor, laughing. Toby poked fun at his inability to do something that so many other people have no problem with. Holly J. then confided in him about her own insecurities regarding being in her older, popular sister's shadow all the time. Toby told Holly J. that she was filling Heather's place at Degrassi just fine, which touched her. Unbeknownst to the two, Holly J.'s friends were watching them, astonished at the fact that Holly J. seemed to be enjoying Toby's company. Ashamed of being "found out" by her clique, Holly J. insulted Toby and joined her friends.
Later, Holly J. approached Toby and told him that she was willing to date him, even if it meant "lowering" her standards. Now aware of Holly J.'s cruel personality, he turned her down and said, "Toby Isaacs calls the shots."
In Party Etiquette, Holly J. attempts to have a secret "thing" with Toby, but Liberty Van Zandt catches them together. She is angry since she and Toby also had a "thing", which causes Toby to run while both girls hunt him down.
- They had feelings for each other.
- They both are friends with Emma Nelson.
- Holly J. had a conflict with Toby's friend Manny Santos.
- They both served as Vice President of the Degrassi Student Council.
- They attended Degrassi Community School together for one semester in 2007.
- They both graduated from Degrassi: Toby in 2007 and Holly J. in 2011.