• Jay Halstead and Hailey Upton Relationship Timeline on Chicago P.D.

  

  One Chicago fans were able to see Jay Halstead and Hailey Upton’s relationship on Chicago P.D. coming from a mile away. From the moment Halstead and Upton became partners within the Intelligence Unit, it was also fairly clear that the partnership was going to turn romantic. It was simply a matter of when. The show wasted little time when it came to creating an “Upstead” fan base, then it gave shippers exactly what they wanted and so much more.

  The couple’s popularity ensured that Jay Halstead and Hailey Upton’s relationship on Chicago P.D. wasn’t just a prominent part of their story — it was a central aspect of the entire show. For several seasons, Upstead’s ups and downs not only strengthened their dynamic, but helped to drive the series’ plot. While it all came to an end with Halstead’s abrupt departure, there are still many Upstead moments that carved out places in Chicago P.D. history.

• Season 5, Episode 1: Upton Supports Halstead After His Shooting Scandal

  

  Upton’s first episode as a series regular also included the very first Upstead moment. Halstead struggled after a bullet from his gun went through a suspect and accidentally killed an innocent girl. Though a public statement from Ray Price cleared Halstead of wrongdoing, the victim’s death still weighed on him, and Upton was there mere moments afterward to comfort her new partner. She confided that she had also been involved in a shooting, and that created the bond they’d rely on for years to come.

• Season 6, Episode 10: Halstead Is Totally Not Jealous About Upton and Ruzek

  

  Chicago P.D. Season 6 surprised fans when Upton and Adam Ruzek hooked up, and they weren’t the only people caught off guard. Halstead found out about the relationship in “Brotherhood” when he walked in on Upton and Ruzek disagreeing. His reaction and Upton’s reaction to his reaction had serious Upstead vibes. “We’re good. And we’re always going to be good,” Halstead assured an apologetic Upton, but she clearly cared how he felt, and he clearly cared about her.

• Season 7, Episode 10: Upton Refuses to Leave a Wounded Halstead

  

  The seventh season used a genre trope to move Jay Halstead and Hailey Upton’s relationship on Chicago P.D. forward. Halstead’s being shot prompted Upton to rethink her feelings about her partner. While the rest of the team worked the case, she remained at Chicago Med. “It’s hard because you love him,” Vanessa Rojas said to Upton, who brushed it off with, “Of course I love him. He’s my partner.” But the look she gave said differently — and she nearly told Halstead how she felt before his phone interrupted.

• Season 8, Episode 3: Halstead and Upton’s First Kiss

  

  Tracy Spiridakos’ crossover appearance on FBI also allowed Chicago P.D. to finally make Upstead an official couple. Upon returning from her stint working in New York, Upton revealed to her partner that she had been offered a fantastic job — and that he was the primary reason she rejected it. “It’s been a long time since I’ve seen you as just my partner,” she bashfully confessed. Halstead responded to this information by giving her a passionate kiss, and there was much rejoicing from One Chicago fans.

• Season 8, Episode 16: Upton Proposes to Halstead

  

  The Chicago P.D. Season 8 finale “The Other Side” was full of surprises, but the biggest came at the end, when a shell-shocked Upton impulsively suggested to Halstead that they should get married. After shooting Kim Burgess’ tormentor Roy Walton, she was even more grateful for Halstead being a “decent” man and didn’t want to lose him. The scene was the opposite of Halstead’s Season 4 cliffhanger, when he’d intended to propose to Erin Lindsay, and showed how much Upton had grown through their relationship.

• Season 9, Episode 4: Halstead Confronts Voight About Upton

  

  Upton’s guilt over her involvement in Roy Walton’s death continued into Season 9, and it naturally had an effect on Upstead. After seeing how much Upton was struggling, Halstead called a late-night meeting with Voight and interrogated him. “You let her cover for you,” he said over a shot of Upton drowning her sorrows in alcohol. “Have you seen what it’s done to her?” When Voight told Halstead he didn’t know the woman he was sleeping next to, Halstead punched him.

• Season 9, Episode 9: Upton and Halstead Get Married

  

  Jay Halstead and Hailey Upton’s relationship on Chicago P.D. hit its high point when the couple tied the knot in Season 9. In keeping with the series’ grittier tone, they didn’t get a big wedding. Instead, they had a quick ceremony after Halstead insisted they get married immediately. Upstead fans were treated to one of the steamiest scenes in Chicago P.D. history when the couple celebrated their new relationship status. Unfortunately, their wedded bliss lasted less than a season due to Jesse Lee Soffer’s departure.

• Season 9, Episode 13: Halstead Rushes to Med to Check on Upton

  

  After Upton stayed by his side in Season 7, Halstead showed up at the hospital for her in Season 9, after she dove into the water to save victims of a car accident. Though Upton was already leaving, Halstead’s worry for her was clear on his face and he made sure to stop her and give her a much-needed hug instead of just letting her rush back to work. He was also right there with her at the episode’s climax, helping Upton save another life, even though the man they saved was actually their suspect.

• Season 10, Episode 3: Halstead Leaves Chicago — And Upton — Behind

  

  Jesse Lee Soffer leaving Chicago P.D. was shocking, but the way Halstead was written out was worse for Upstead fans. Having a crisis of conscience over a shooting, he not only chose to resign from Intelligence but accept an Army assignment in Bolivia. “What are you talking about?” blurted Upton, speaking for the audience. But Halstead had taken the job without asking her and already scheduled a same-day flight out. Plus, Jay calling her “the love of my life” didn’t make his final appearance any better.

• Season 10, Episode 20: Upton Takes Off Her Wedding Ring

  

  Chicago P.D. Season 10, Episode 20, “Fight” would have been a great Upstead episode, as Upton was in an emotional, life-threatening situation. However, it was  the exact opposite because it seemingly ended Upton and Halstead’s marriage. Upton confessed to Hank Voight that she hadn’t called her husband and “He’s not even gonna know I was gone.” Voight encouraged her to let go, and after seeing all the places around their apartment where Halstead used to be, a tearful Upton ended the hour by removing her wedding band.

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