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A Look Back at Halstead and Upton's Slow-Burn Romance on Chicago P.D.

Though it took a few seasons, Upstead was always inevitable.

First Look | NBC's One Chicago 2022

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.

Season 4

Jay and Hailey Relationship

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. 

Season 5-7

Jay and Hailey having a conversation

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.

Jay and Hailey standing in front of a judge

"It really was the perfect way for that to happen. It really stays really true to those two characters," Spiridakos told TV Insider. "It wasn’t a big celebration because it’s just for the two of them. Things have been so fractured for so long between them that it was a moment for the two of them to reconnect and kind of show that they’re in this together and they’re going to move forward together." 

Season 10

Unfortunately, Upstead fans everywhere were let down when Soffer's exit from the show (following Episode 3's "The Great Man") meant that we'll no longer see the couple on our screens.

After becoming unhappy with the increasing gray areas in his policing, Halstead resigned from the Intelligence Unit and left Chicago—which meant he also left Upton. The detective took a job with the army to hunt down drug cartels in Bolivia.

"It's black and white, it's good and bad, it's right and wrong, and it's no more of this," he told Upton about his new job. "I need that. I need that back. I fly out today. It's not forever, it's eight months, maybe a little longer. But I swear to you that we're gonna get through this because you're the love of my life, and if I'm yours, then you'll know that you have to let me go."

Despite springing that he was moving thousands of miles away with basically no notice, his words leave the tiniest bit of hope for fans. But this heartbreak will be tough for Upton to get over.

Halstead and Upton in Chicago PD Season Premiere

"Hailey's really going to have to go through it this season," showrunner Gwen Sigan tells NBC Insider. "She's someone that doesn't love dealing with emotion, doesn't love confronting it head on. She's naturally guarded, she wants to be strong, and she also wants to be strong for Jay too. He asked her for this, he said he needed it, and she loves him."  

Sigan continued, "But, the reality is, she's been left behind.  And that's gutting.  We'll see her deal with it by first seeking distraction—diving into work, putting all that feeling into the job—and when a case pops off that really gets inside her head, that distraction quickly turns to an obsession.  It's an interesting path for her, fueled by a lot of emotion and denial." 

Watch Chicago P.D. on NBC Wednesdays at 10/9c and next day on Peacock.

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