Chicago P.D.'s Tracy Spiridakos And Jesse Lee Soffer Break Down Upstead's Big Proposal Twist, And What Comes Next


Major spoilers ahead for the Season 9 premiere of Chicago P.D. on NBC!

The Season 8 finale of Chicago P.D. packed in plenty of cliffhangers before the final credits rolled, with the episode ending on a shaken Upton surprising Halstead with a proposal. It wasn't the most romantic scenario in the world considering the timing, and the finale ended without revealing Halstead's answer. The Season 9 premiere finally revealed what's up with Upstead, but with a twist on the proposal when Halstead flipped the script in the final scene to propose to her. Stars Tracy Spiridakos and Jesse Lee Soffer broke down the big scene.

As it turned out, Halstead didn't give her an answer one way or the other when Chicago P.D. picked up where it left off on her proposal, and they didn't get engaged until they had a conversation about why she did it. Then, it was Halstead who went down on one knee, in a scene that was very sweet, but also complicated by the fact that Halstead is completely in the dark about Upton and Voight's secret. When I spoke to the Chicago P.D. stars in separate interviews, they shared how they approached the proposal scene with the big secret still between their characters. Tracy Spiridakos shared:

I think Hailey had to, just in the moment with him, as opposed... That was, I'm trying to remember, there was a little bit of a conversation about it, where he says, 'Did you mean what you said?' essentially. And she did, she very much did and and her proposal to him came from a really vulnerable place, but it was a truthful [proposal], that is how she feels. And she does love him. And so when it comes up again, she's like, 'I meant everything that I said, and if you don't believe that, you don't believe me,' you know? And, yeah, it was really fun to play. I think being vulnerable is always, like as a person playing vulnerable, you're still vulnerable. So it's always like, you know, I get awkward and [laughs] whatever. I do, anyway. But Jesse's so great, and we had a good time playing it. And I'm excited to see it.

There were a lot of layers to not only Upton and Halstead's first interactions over the initial proposal, but also the conversation leading up to the second one with Halstead going down on one knee. The conversation at the end of the episode came when Upton was calmed down somewhat from the opening scene, and Tracy Spiridakos and Jesse Lee Soffer played it in a way that got their characters on the same page when it comes to their relationship... if not on the same page when it comes to what Upton is hiding.

Jesse Lee Soffer previously shared that Halstead isn't going to stay in the dark about what Upton and Voight did forever, so fans shouldn't necessarily expect nothing but smooth sailing for the good ship Upstead when looking ahead to the rest of Season 9. Soffer also shared his perspective on the second proposal scene with his character still not in on the secret, and how Halstead feels about the whole situation after being taken completely by surprise, saying:

You know, it's tough. Sometimes you got to stay really present with what's going on with the character, what the character has been through, and you just kind of try to stay in exactly everything that you've lived as that character up to that very moment, and then try to stay present. Because, you know, you might have a hard time justifying something, or you're not sure where the character's coming from, with why they're making a choice that they're making. But, you know, that's what we did. We talked about the scene. And obviously Jay has loved Hailey for a long time, and it's something that he wants, and whether or not he's got a suspicion that there's more to this story right now and this kind of came out of thin air, that doesn't matter. And he says, 'Okay, let's go forward with this. I'm not going to say no to you.' And that's kind of, that's where it came from. So it's going to be fun to play out.

Chicago P.D. may have started out Upstead's engagement with a big secret hanging over them, but Jesse Lee Soffer's comments about Halstead's feelings for Upton seem pretty encouraging about where Season 9 will take the storyline. While it may cause some distrust between them, Soffer also previewed that fans will see how the situation will play out with Halstead and Voight once Halstead finds out. Does that mean he'll cast more blame on Voight than on Upton, even if she kept the secret from him in a more intimate way? Or will it be worse news for Upstead?

As somebody who has been on Upton's side ever since Voight manipulated the situation in the Season 8 finale to turn Upton's good shoot to save her sergeant into a very dirty secret, I definitely hope that Halstead joins me on Team Upton. Voight really did back her into a corner, and there's no good way out for her. At this point, I wouldn't blame the women of the Intelligence Unit if they decided to retire from CPD and star in a spinoff called Chicago Florists where nothing bad ever happens to them. It's been a rough couple of years!

In all seriousness, the show set the stage for a layered ninth season. While there were some happy conclusions to the cliffhangers thanks to Upstead getting engaged and Burgess surviving, things are never too smooth for too long for the cops of Chicago P.D. See what happens next with new episodes of P.D. on Wednesdays at 10 p.m. ET on NBC, following new episodes of Chicago Fire at 9 p.m. ET and Chicago Med at 8 p.m. ET.

Laura Hurley
Senior Content Producer

Laura turned a lifelong love of television into a valid reason to write and think about TV on a daily basis. She's not a doctor, lawyer, or detective, but watches a lot of them in primetime. Resident of One Chicago, the galaxy far, far away, and Northeast Ohio. Will not time travel and can cite multiple TV shows to explain why. She does, however, want to believe that she can sneak references to The X-Files into daily conversation (and author bios).