|“||I figured now that you're starting a family of your own that... It would be a good time to make amends.||”|
— Jenna to Toby
Their relationship is extremely tempestuous, especially due to the fact that Jenna pursued and blackmailed Toby into entering a sexual relationship with her during their younger years.
There's No Place Like Homecoming Toby meets with Jenna who warns him that Emily will hate him when she finds out his secret. The Homecoming Hangover Jenna is seen crying in front of the Cavanaugh house, maybe suspecting he's dead due to his smashed up motorcycle. Salt Meets Wound Jenna tells Toby she was the one who turned him into the cops in order to keep him close. He rejects her, so she angrily slaps him. The New Normal Jenna is rebuffed when Toby accepts Spencers offer to give him a ride to the station instead of riding in a taxi with her. Monsters in the End Jenna calls Toby to drive her to school.
Jenna: There is nothing wrong with us, Toby. We're not really related.
Jenna: Do you like my costume?
Toby: It's nice. But you know... [he covers her one eyes so she can't see] I liked you better like this.
Jenna: I figured now that you're starting a family of your own that... It would be a good time to make amends.
Toby: Yeah? I remember we tried that about three years ago and it didn't go so well.
Jenna: Yeah, maybe not. But I would really like to try again.
Marco: Not sure how much threat a blind girl can be.
Toby: You haven't met Jenna.
Jenna: Toby? I know this may seem weird, but... I don't think Spencer's-Spencer.
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