‘Chicago P.D.’: Complete Timeline of Jay Halstead and Hailey Upton’s Relationship

Article Highlights:

  • Jay Halstead and Erin Lindsay dated in the first four seasons of Chicago P.D.
  • Jay Halstead and Hailey Upton met in season 5
  • Does Jay Halstead get married in Chicago P.D. Season 9?
Hailey Upton and Jay Halstead from 'Chicago P.D.' Season 9
Tracy Spiridakos as Hailey Upton and Jesse Lee Soffer as Jay Halstead | Matt Dinerstein/NBC/NBCU Photo Bank

Fans ready to watch Chicago P.D. Season 9 can’t wait to see how Jay Halstead and Hailey Upton’s relationship progresses on the show. At the end of the Chicago P.D. Season 8 finale, Upton proposes to Jay, leaving him speechless and shocked. So, how did their relationship begin in the first place? Here’s a relationship timeline and where things might be headed next.

Jay Halstead and Erin Lindsay dated before Halstead and Hailey Upton

In the early days of Chicago P.D., many fans wondered: Do Jay Halstead and Erin Lindsay end up together in the end? The two got their start on Chicago Fire in totally different relationships, but once they joined Chicago P.D., it looked like it was full steam ahead on their relationship. In the first four seasons of the show, fans couldn’t get enough of Lindsay and Halstead.

While it looked like Lindsay and Halstead were destined to stay together through the entirety of the series, the show had to make a decision for the couple when Lindsay actor Sophia Bush chose to leave the show. One Chicago Center reports the show gave Halstead an ex-wife, and he decided to end his relationship with Lindsay because of this new factor. Later on, Halstead decided he wanted his relationship with Lindsay back and aimed to propose. Unfortunately, when Halstead called Lindsay, she never answered. Then, she left the series completely.

Jay Halstead and Hailey Upton met in ‘Chicago P.D.’ Season 5

Jay Halstead and Hailey Upton from 'Chicago P.D.' Season 9 standing next to each other
Jesse Lee Soffer as Jay Halstead and Tracy Spiridakos as Hailey Upton | Matt Dinerstein/NBC/NBCU Photo Bank

Now, Jay Halstead and Hailey Upton are front and center for the show’s romance. Now that Chicago P.D. Season 9 is here, we’re sure to see more of their relationship. The two met during Chicago P.D. Season 5 when Upton joined Intelligence as Halstead’s partner, Distractify notes. Their relationship started just as friends, as Halstead was still dealing with his heartbreak over Lindsay. But over time, they developed feelings.

By Chicago P.D. Season 7, it was clear a connection was developing between Halstead and Upton. But executive producer Rick Eid noted he didn’t want to rush things. “There’s definitely a pretty powerful connection there … It’s just whether they choose to act on it, and when, and what that looks like,” he told TVLine at the time. “It’s definitely in play.”

By Chicago P.D. Season 8, their relationship ramped up. Distractify notes Upton tells Halstead how she feels, and the two kiss in episode 3. The season also has Halstead telling Upton he loves her prior to Upton’s surprise proposal.

Does Jay Halstead get married? He’ll have to make a decision in ‘Chicago P.D.’ Season 9

Jay Halstead and Hailey Upton from 'Chicago P.D.' Season 9
Jesse Lee Soffer as Jay Halstead and Tracy Spiridakos as Hailey Upton | Matt Dinerstein/NBC/NBCU Photo Bank

So, does Jay Halstead get married to Hailey Upton in Chicago P.D. Season 9? At the end of the Chicago P.D. Season 8 finale, Upton proposes to Halstead out of nowhere, leaving him shocked. He didn’t give an answer just yet. Either way, no matter how he answers Upton, we’re sure he’ll want to get to the bottom of why she’s asking. And it seems likely he’ll figure out Upton’s current source of anxiety, which is that she shot a suspect and Hank Voight got rid of the body in season 8.

Eid talked about what’s next for the couple, too. “He’s very much in love, but also aware that he’s in love with a complicated person,” Eid said regarding Halstead, according to TV Insider. “He’ll take his time to determine where this proposal is coming from.”

The Chicago P.D. Season 9 premiere date is Sept. 22, 2021, at 10 p.m. EST on NBC.

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