Imogen and Winston became friends through spending time together during various school events, and clubs. The two first became aqquainted while working for Degrassi TV, during which time they were shut down after portraying student council in a negative light. This lead to the pair protesting Drew's presidency, along with other students who supported their cause. Imogen also directed and produced Winston's musical, Captain Who, as well as giving him romance and relationship advice about his then girlfriend, Frankie Hollingsworth.
In You Oughta Know, Imogen creates a club called Degrassi TV and hosts auditions for on-air personalities. After combing through dozens of bad auditions including Winston’s. Imogen tells Becky Baker that she’s chosen Winston to be Degrassi TV’s anchor.
In Black Or White, Drew uses his position of power to pull the plug on Degrassi TV and fire Winston, and Imogen quits in protest. Winston and Imogen lead a group of protesters who want to have Drew impeached. Drew reinstates Degrassi TV which in turn Winston and Imogen return, and instead of a carnival, he vows to use budget money to host a Thanksgiving feast for needy families, Winston and Imogen agree on this.
- They are both friends with Maya Matlin.
- Winston had a conflict with Imogen's good friend, Drew.
- They both worked on Degrassi TV.
- They both wear glasses.
- Imogen agreed to direct Winston's play, Captain Who.