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Spoilers ahead for the episode description of Chicago P.D.'s Season 7 winter finale, called "Absolution."
Chicago P.D. has been relatively light on the Jay Halstead front throughout Season 7, with the exception of his conflict with Voight early on and the difficult case of a couple of murdered boys more recently. According to the description for the winter finale, however, Halstead has been keeping a big secret: he's been in a relationship on the down-low. As if that's never backfired on him before! This time, though, it could impact Upton.
First, let's get into what's happening for Halstead. "Absolution," which airs on November 20 as the final episode of Chicago P.D. in 2019, will go down like this:
Halstead's secret ongoing relationship with a woman connected to another case puts him in jeopardy.
Oh, Halstead. Did you learn nothing about dating people involved in investigations from the Camila fiasco back in Season 5? Admittedly, Halstead was noticeably a mess in Season 5 as he spiraled while keeping his relationship with Camila (who turned out to be a drug dealer) a secret, and I'm guessing he's not hooking up with this new woman under the name "Ryan" this time. It probably won't be as bad as Camila; is there any way it could go well for him, though?
Of course, it's possible that this "secret ongoing relationship" won't be that big of a deal and isn't actually inappropriate. The cops of Intelligence don't have to tell each other everything, after all, and if Halstead wasn't talking about it at work, how would viewers have found out? Season 7 has been heavier on the procedural elements than on characterization.
Still, if the relationship puts him in danger, I'm guessing he kept it secret for a reason beyond just wanting some privacy. This relationship may not be on the Camila end of the spectrum, but that doesn't mean it's on the up-and-up.
So, what does this mean for Upton? Chicago P.D. showrunner Rick Eid teased the potential of a Halstead/Upton romance earlier in the fall season, referring to their "mutual attraction and connection" while noting that they "both take their jobs very seriously."
The latest episode, which saw Upton struggling with the death of a C.I. possibly at the hands of Darius Walker, featured some serious gazing from Halstead, although it could have been... friendly gazing? More likely that it was concerned gazing, but it's clear that the bond between Halstead and Upton is just about as strong as procedural bonds can be.
If an Upstead romance does happen, fans will likely have to wait until whatever happens with Halstead and this secret woman runs its course. While Chicago P.D. has used vague episode descriptions to conceal a huge plot twist for one of the major characters -- such as the bombshell reveal of Burgess' apparent pregnancy after a description that simply mentioned a "diagnosis" -- before, I don't consider it very likely that Upton is Halstead's secret girlfriend.
The reveal that Halstead has been secretly seeing somebody may explain what Jesse Lee Soffer, who of course plays Halstead, told CinemaBlend and other outlets at the One Chicago press day about whether a Halstead/Upton romance could happen:
I don't know. I think if that were to happen, Jay would have to get his stuff together. Because, they get closer and there's a bond and they trust each other and Jay goes off the rails and does something crazy, and Upton has to reel him back in. So, that would have to shift in some way.
Will the winter finale (or aftermath) be another situation in which Upton has to reel Halstead back in? If so, I can't blame her for not going for a relationship with Halstead any time too soon. She already went through the drama of her relationship with Ruzek (who is 'a little broken' this season) in Season 6, and she may not have forgotten how the Camila fiasco went down back in Season 5 when she and Halstead were still relatively fresh partners.
Whatever happens with Halstead's secret relationship, I have to hope that he and Upton remain close friends. Their bond is one of the strongest of the series, and it would be a shame to lose that, whether they remain platonic or pursue something more down the line. It's not like P.D. will be missing any inter-unit romance if Halstead/Upton doesn't happen. Ruzek and Burgess hooked up at the end of the "Infection" crossover, and something may be happening with Atwater and Rojas next.
The good news is that fans will soon get to find out what's happening with Halstead, as the winter finale of Chicago P.D. airs Wednesday, November 20 at 10 p.m. ET on NBC, following the winter finale of Chicago Fire (with the return of none other than Gabby Dawson) at 9 p.m. ET and the winter finale of Chicago Med (possibly with Natalie regaining some of her memories) at 8 p.m. ET.