Are Upton And Halstead Back Together?
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Warning: Spoilers Ahead for “Chicago Fire” Season 14, Episode 13 — “Reckoning, Part I,” “Chicago Med” Season 11, Episode 13 “Reckoning, Part II,” and “Chicago P.D.” Season 13, Episode 13 — “Reckoning, Part III”

After several months apart, Hailey Upton (Tracy Spiridakos) and Jay Halstead (Jesse Lee Soffer) reunite in a gripping crossover event in the One Chicago franchise. The big question is whether their romance still has a spark. The answer is a tentative “maybe” as the former couple navigates unresolved feelings, culminating in a promise to share a drink and talk things over.

Hailey, now an FBI Special Agent stationed in Detroit, learns that Jay’s mission in Bolivia is on the verge of disaster and steps in to assist. When Jay rescues her from an attacker, they join forces to uncover the mystery behind a drug mule who unleashed a deadly toxin on a plane, claiming over a hundred lives, including his own. In the aftermath, Jay confesses to Hailey that he regrets not reaching out sooner and apologizes for how their relationship ended. Hailey is open to reconciliation, agreeing to further discussions rather than immediately returning to their respective duties.

But is romance truly rekindling? Tracy Spiridakos offers a cautious perspective: “For Hailey, it was a conversation that opened the door to more discussions,” she shared with NBC Insider. “She was deeply hurt by their separation, but their shared history, beyond just romance, is significant.”

Hailey’s hesitation in forgiving Jay is understandable. Their bond strengthened during their partnership in the field, leading to marriage in Season 9 of “Chicago P.D.” However, by Season 10, Jay struggles with the ethical complexities of police work and decides to resign. He embarks on his mission in Bolivia without informing Hailey or their colleagues, ultimately ending their marriage from afar. This abrupt departure left fans of “Chicago P.D.” outraged and left Hailey grappling with the fallout. Both Hailey and Tracy Spiridakos eventually departed from the show in Season 11.

Hailey and Jay were in a rough place when they saw each other last

It’s no wonder that Hailey is so reluctant to forgive Jay. After the pair become close while serving as partners in the field, they marry during Season 9 of the police procedural. But during Season 10, Jay realizes he’s unable to cope with the moral nuances of police work and quits the force. 

He takes up his aforementioned Bolivian mission without telling Hailey or anyone else on the team, and divorces her long-distance. All in all, it’s a bizarre exit that made “Chicago P.D.” fans livid. Hailey struggles in the wake of his abandonment, and both Upton and Tracy Spiridakos ultimately exited the show during Season 11.

But that’s all water under the bridge now. Even though they aren’t officially reunited as a couple yet, at least one person thinks there’s blue skies ahead for the star-crossed duo. “I think there’s definitely hope there,” “Chicago P.D.” showrunner Gwen Sigan told TV Insider. “I think they’re different than they were years ago. I think they’re in a better spot, each of them in their own lives. And I think they have new perspective on everything that happened between them all those years ago. So, yes, I think there’s hope.” While Spiridakos and Jesse Lee Soffer aren’t returning to the procedural any time soon, at least those who love Upstead finally have a reason to smile.



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