The crew of Brooklyn Nine-Nine accumulated more than a few enemies throughout the course of the series, but the most annoying villain in their lives was Teddy Ramos, formerly known as Teddy Wells. Teddy didn’t mean to be a bad guy — but his unrelenting pursuit of Amy Santiago made him a thorn in the side of the entire precinct.
While it was obvious that Amy and Jake Peralta were going to end up as the show’s next married couple from moment one, standing in their way was Detective — and eventually Lieutenant — Teddy Wells. He made his debut in Season 1, Episode 19 “Tactical Village,” when different precincts sent their best officers to the annual Tactical Village event. While the Nine-Nine managed to pull off the win despite the usually hapless Scully being on their team, Jake suffered a major personal loss as the day started a courtship between Amy and Teddy.
It was only a few episodes before in Season 1, Episode 13 “The Bet” that Jake had realized he had romantic feelings for Amy. Unfortunately, he waited too long to do anything about them and Amy ended up in a relationship with Teddy that lasted almost a full season. In Season 2, Episode 9, “The Road Trip,” Amy and Teddy broke up on what may have been the most awkward trip to maple syrup country of all time. It involved a closet full of unnecessarily creepy marionettes.
Amy and Jake eventually got together in Season 3 — but despite the fact that their relationship became more and more solid as the series went on, Teddy never really went away. He kept popping up, almost always proposing to Amy on the spot. On several of these occasions, Jake was standing right there! Season 5, Episode 22, “Jake & Amy,” when Teddy made several attempts to propose to his ex on the day of her wedding to Jake. The constant proposals were Teddy’s own unique brand of sadness and awkwardness.
Being in another relationship didn’t stop Teddy, either. In Season 4, Episode 13 “The Audit,” Teddy and his then-girlfriend Rachel took Jake and Amy to “jazz brunch.” Of course, Teddy proposed to Amy in front of Rachel, instantly ending his relationship with her. In Season 7, Episode 12 “Ransom,” Teddy returned yet again, this time revealing that he was married and had taken his wife’s last name of Ramos — but still used the opportunity to propose to Amy. His thought process was more confusing than Rosa Diaz’s vague backstory or Jake not looking for his siblings.
Teddy’s constant, creepy persistence made it impossible for Amy, Jake or anyone else in the Nine-Nine to attempt to build a friendship with him. Every time Amy was even remotely nice to him, Teddy took it as a sign that she wanted him back. His inability to let Amy go was neither appropriate nor endearing, and it not only made the entire precinct wary of him, it also made him one of Brooklyn Nine-Nine‘s most aggravating bad guys.
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