|Started Dating||Karma Chameleon (204)|
|Dating Status||Broken Up before Ghost in the Machine (1) (401)|
In Karma Chameleon, a mutual love for anime leads to a mutual crush between Toby and Kendra. However, when Spinner Mason informs Toby that he is Kendra's older adoptive brother and threatens to beat him up if he doesn't stay away from her, Toby reluctantly avoids Kendra. At first, Kendra is confused as to why Toby is suddenly avoiding her until she figures out that he is afraid of Spinner; so she calls him a coward and walks away. Finally, Toby gathers up the courage to approach Kendra right in front of Spinner. Kendra is proud when Toby states that he is willing to risk getting beat up by Spinner for the opportunity to have a relationship with Kendra. Fortunately, Spinner agrees to let Toby talk to his sister under the condition that he doesn't break her heart.
In Careless Whisper, Kendra is feeling smothered with too much affection from Toby. She deals with it for a while until she finally tells him how she feels. Toby is upset because he believes that Kendra actually wants to break up with him. To fix the issue, Kendra kisses Toby and tells him that she enjoys his company but she would appreciate a little space every now and then; Toby understands.
In Dressed In Black, Spinner is furious when he discovers condoms in the locker that J.T. and Toby share. This leads him to believe that Toby is trying to have sex with Kendra. Unaware that the purchase of condoms was J.T.'s idea, Kendra angrily confronts Toby and calls him a pervert for thinking that she would even consider having sex with him when she was only twelve years old. Later that day, Spinner prepares to beat Toby up until the latter quickly assures him that even if he did plan on having sex with Kendra (which he didn't), he only purchased the condoms to make sure that they'd be safe. When he adds that the condoms were J.T.'s idea, Spinner humiliates J.T. by wrapping him up in glow-in-the-dark condoms to teach him a lesson about the pressures young teens already face to have sex.
Toby and Kendra have no plots together in this season. However, they are seen together several times and it is obvious that they are still together.
In It's Raining Men, Toby and Kendra are both at J.T.'s party to watch his commercial.
In The Power of Love, the two attend the Bollywood themed dance as each other's dates, and can be seen walking around in the background together.
Kendra was last seen in the The Power of Love, the season three finale, prior to vanishing into what is known as the Degrassi Black Hole. In Ghost In The Machine (1), Toby briefly states that he and Kendra had broken up over the summer. After that, Kendra is never again mentioned by anyone.
- Start Up: Karma Chameleon (204)
- Broke Up: The August before Ghost in the Machine (1) (401)
- Reason: Unknown
- Toby was scared of Kendra's elder brother Spinner Mason.
- They both liked comic books and anime.
- They were each other's first girlfriend/boyfriend. Kendra is Toby's only known girlfriend.
- Toby's close friend Emma Nelson married Kendra's brother Spinner.
- Toby's stepsister Ashley Kerwin was friends with Kendra's brother Spinner.
- They were both members of the Rooks & Knights Society.