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While Colleen and Fry date, Fry constantly flatters her by saying she looks beautiful while Coleen replies with less interest perhaps due to having all her other boyfriends. She has four other boyfriends besides Fry.
It's only through their relationship progressing from co-workers to friends that they evolve and learn to balance each other out. Fry matures because of Leela keeping him in check, and Leela learns that her "standards" are all wrong, as most of the guys she ends up dating are douchebags.
He briefly dates Colleen, who is a police chief. In "Game of Tones," Fry's apartment has a calendar with a muscular woman on it (see image below). And then, of course... there's Leela.
May 29, 2021 · The pair tried to continue a romance, but Fry found himself unable to accept her polyamorous relationship with other men. Fry and Colleen split apart, with a despondent Fry venturing into the crack in the universe and meeting Yivo, a massive alien life-form that used him to attack Earth and try to assimilate it into a "relationship."
- Senior Staff Writer
When the tear in the universe was caused, Fry and Colleen were brought together by fear. After discovering Colleen had four other boyfriends when Fry decided to move in with her, Fry broke up with Colleen. At the end of The Wild Green Yonder, Fry and Leela profess their love for each other and kiss as the Planet Express ship enters a wormhole.
Fry starts dating a girl named Colleen, but breaks up with her when he discovers she has many other boyfriends. At a conference, Professor Farnsworth proposes an expedition to investigate the anomaly.
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Beast With A Billion Backs shows a flashback to Fry meeting Colleen almost immediately after the rift opens. They've been together about a month. Fry didn't necessarily "get over" Leela.
