Amy and Teddy met at a voluntary training course to brush up on police codes. The two bonded while studying, and went out on a couple of dates. The relationship ended when Teddy was stationed in Queens.
He and his team scored a perfect run in the Tactical Village weapons training course. They set the record of 18 mins and 41 seconds. Their record was then, beaten by the Nine-Nine squad, who scored 18 mins and 28 seconds.
Teddy and Amy soon rekindle their relationship, dating exclusively for over six months.
In The Road Trip, Jake Peralta invites him on a trip upstate, wanting to surprise Santiago. He ends up making things awkward as Santiago had planned to break up with Teddy, mainly because of his obsession with pilsners, a type of pale lager. Teddy suspects the breakup also might have been related to Jake confessing his feelings for Amy on several occasions.
In The Audit, he is chosen to oversee whether or not the 99 is worth keeping around when Brooklyn plans on shutting down a precinct. Fears over him having hard feelings on his break up with Amy cause her and Jake to suck up to him and his love for Pilsners. At a "Jazz Brunch" he organises between himself, the pair and his own girlfriend, Amy and Jake fake a fight to avoid rubbing their relationship in his face but this leads to him revealing to Amy that he still has feelings for her (in front of his girlfriend) and proposing to her (in front of his girlfriend). She rejects him and the next day he embraces his role as "The most boring man in America" and hands the role of Auditor to Veronica Hopkins. But not before trying another attempt at proposing to Amy.
Teddy took to heart Amy's words about him being the most boring man alive. To "level up his cool", Teddy began traveling and eventually joined and soon led the bomb squad. He remained in love with Amy, advised by his therapist to just stop trying to get over her. In Jake & Amy, his team responds to a call about a bomb threat at Jake and Amy's wedding. Teddy again tries and fails multiple times to win Amy back. The bomb was eventually found when Boyle volunteered to squeeze into the last vent not inspected in the building, and his team went on to do their work, forcing the couple to give up on having the wedding at the original venue. He later attended their wedding at the precinct and brought his squad's bomb disposal robot to serve as the ring-bearer, to Jake's extreme delight, and left, but not before lightheartedly trying to object to the union.
Amy is Teddy’s ex-girlfriend. She broke up with him due to her feeling for Jake Peralta after he confessed that he had romantic feelings for her before and after going undercover. This caused Amy to be confused, resulting in their relationship getting “out of sync.” She and Teddy broke up in the episode “The Road Trip.” Since then, Teddy has not gotten over Amy and continues to propose to her, despite Amy’s repeated rejections.
- Main article: Pilsners
When Amy was dating Teddy, his love of pilsners was a running gag throughout the series. It is eventually a large part of the reason Amy broke up with him.