If there’s one perfect example of a slow-burn romance, it’s that of Jay Halstead (Jesse Lee Soffer) and Hailey Upton (Tracy Spiridakos). Chicago P.D.’s “Upstead” didn’t have their first kiss until four seasons after they met, with their love story only recently picking up on the series.
But that doesn’t mean that fans didn’t see the writing on the wall. Below, we take a look back at Halstead and Upton’s relationship history on the show.
Upton is first introduced to both Halstead and the rest of the Intelligence Unit in Episode 21, titled “Fagin.” At the time, she’s a detective in Robbery-Homicide and collaborates with Intelligence on its latest case. This marks the first time she and Halstead work together, though he was still partnered with Erin Lindsay at the time.
Once Lindsay left the show and Upton came on as Halstead’s partner in Intelligence, the two became increasingly close—but without making their relationship romantic. From Upton encouraging Halstead to go to therapy for PTSD to her opening up about her childhood abuse—and even kidnappings, suspected murder, and multiple near-death experiences—the two’s bond slowly grows beyond their police work. Even when Upton dates Ruzek in Season 6, it does little to break her friendship with Halstead.
By the end of Season 7, it’s clear Upton and Halstead have the potential to take things to a romantic level—especially during the tenth episode, “Mercy,” when Upton doesn’t leave Halstead’s side in the hospital after he’s shot. In response to Rojas’ remark that she loves Halstead, Upton replies, “Of course I love him, he’s my partner,” revealing her true feelings.
Later on in the Season 7, “Silence of the Night,” fans see both cops openly admit that they miss one another when Upton is tasked with going to New York to work with the FBI.
Season 8
Finally, after four seasons, Halstead and Upton have their first kiss in Episode 3’s “Tender Age.” The moment marks the beginning of Upstead, as their romance continues to grow. They say “I love you” to one another in Episode 11, and Voight finds out about their relationship in Episode 14.
By the season finale, shaken by her accidental murder of the suspect in Kim Burgess’ kidnapping (which Voight covers up), Upton proposes to Halstead, saying that she never wants to lose him.
Season 9
By the end of the season premiere, Halstead accepts Upton’s surprise proposal and then asks her to marry him, confessing that he knew for years that they were meant to be. They move in together, with the rest of the Intelligence Unit finally finding out about their relationship, as the two were intent on keeping their partnership strictly professional while on the job.
Later on in the season, amidst the mess caused by the events of the Season 8 finale, Halstead no longer wants to waste time and insists that he and Upton get married ASAP. The two do just that, eloping with a secret courthouse wedding in the season’s fall finale.
