Upstead has not had an easy couple years on Chicago PD. The romantic pairing of Jay Halstead (Jesse Lee Soffer) and Hailey Upton (Tracy Spiridakos) have been subject to FBI investigations, a sudden marriage, and a separation that is still causing emotional strife in the current day.
Between Halstead's decision to leave the show in season 10, and Upton's decision to leave the show in the upcoming season 11, it can be easy to get lost in all the turmoil. Since things are winding down for the couple, as least as far as their time on Chicago PD is concerned, we decided to look back and hit the key moments in their relationship so that you're caught up for the season premiere.
Halstead and Upton meet in S4 E21 ("Fagin")
Jay Halstead has a history of dating the people he works with (much like the actor who plays him, in fact), so the first couple seasons of Chicago PD was characterized by Halstead's romance with Erin Lindsay (Sophia Bush).
Hailey Upton was introduced in while Lindsay was still Halstead's partner, but the season 4 episode "Fagin" marked the first time that Halstead and Upton interacted, as well as worked a case together. There's nothing to suggest that they would eventually become spouses, but there's a definite charm to seeing them cross paths so early in the show.
Upton reveals her true feelings in S7 E10 ("Mercy")
Halstead and Upton got extremely close between seasons 5 and 7, as they became partners and often served as each other confidants. They have each other advice and were often seen chatting when they weren't hard at work. The unspoken attraction between them manifested in the season 7 episode "Mercy", after Halstead is shot and laid up in the hospital to recuperate.
Upton stays by Halstead's side, and she crucially admits her feelings about her partner to Vanessa Rojas (Lisseth Chavez) when she says: "Of course I love him, he's my partner." The pair still take a bit to go on their first date, but this marked a crucial progression, for fans especially.
Halstead and Upton finally kiss in S8 E3 ("Tender Age")
We did it! After years of anticipation and speculation as to when it would happen, Halstead and Upton finally lock lips in the season 8 episode "Tender Age." The kiss comes at the tail end of the episode, in which Upton turns down an offer from the FBI because she wants to stay in Chicago with Halstead.
"Its been a long time since I've seen you as just my partner," Upton said, before her and Halstead embrace. It's a seminal Chicago PD moment, and one that delivered on all the aforementioned hype. A few episodes later, Halstead Upton exchange "I love you"s for the first time, and a few episodes after that, Hank Voight (Jason Beghe) finds out that they're dating.
Halstead and Upton get married in S9 E9 ("A Way Out")
Halstead and Upton ran into some professional issues in season 9, especially when it came to the cover-up that the latter perpetrated with Voight, but that didn't stop the couple from making a huge decision in the episode "A Way Out." After a brief period of engagement, Halstead and Upton decided to get married in private.
The episode ends with the newlyweds enjoying each other's company in a sweet and intimate setting. The rest of the IU doesn't find out about the wedding, in fact, until the following episode. That is the Upstead experience in a nutshell: memorable but ultimately reserved.
Halstead leaves Chicago in S10 E3 ("The Great Man")
This is where things got really tough for Upstead. Halstead decided he couldn't take any more corrupt Chicago dealings and decided to move to Bolivia, where he could easily tell who the good guys apart from the bad guys. All fine and dandy, but he made a promise to return to Upton that he failed to keep.
By the halfway point of season 10, it became painfully clear that Halstead was not putting work into his marriage, and Upton responded by removing her wedding ring. The season 11 premiere is said to be focused on Upton, who we know is on her way out, so we can only hope that part of her reason for leaving is to repair her marriage.