Will Jay turn to Will for wedding advice on Chicago PD: Jesse Lee Soffer’s answer might be reason for concern

Love was in the air in the season 9 premiere of Chicago PD as longtime couple Hailey Upton (Tracy Spiridakos) and Jay Halstead (Jesse Lee Soffer) decided to take their relationship to the next level by getting engaged.

Since the engagement, the couple hasn’t quite been able to enjoy the usual post-engagement festivities choosing to keep their engagement under wraps thus far this season. Of course, secrets can only stay hidden for so long and the hope among fans is that the pair will soon be able to share their happy news with their family and friends in commencing the celebration and planning of their wedding.

However, before the couple gets that far, they’re going to have to overcome quite a significant hurdle in working through the secret Hailey has been keeping from Jay. And while the couple has been through a lot over the years, we’re starting to wonder if wedding bells will be ringing for the couple after all.

Will Halstead and Upton get married on Chicago PD?

Although Hailey and Jay got engaged in the season 9 premiere, the pair have yet to share the happy news with their loved ones and we’re starting to wonder if we’ll ever get that far.

In speaking with star Jesse Lee Soffer before the season began about the possibility of seeing Jay turn to his brother Will (Nick Gehlfuss), who experienced a failed engagement in season 4 of Chicago Med, Soffer seemed to hint that Will might not need to start planning a Best Man’s speech just yet.

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“I think it’s going to be so bumpy at first, that I don’t foresee Will needing to help Jay with his Best Man’s speech,” Soffer playfully teased adding that “If Will is involved, then that would mean that everything is going well and is probably running smoothly for Jay because maybe the marriage is really going to happen.”

The tease definitely seemed to hint that there could be trouble in paradise for Upstead in throwing the odds of them walking down the aisle this season into question. It also seemed to suggest we might not get to see the Halstead brothers teaming up for some wedding planning in the near future, though Soffer is optimistic we’ll get to explore that dynamic at some point this season.

“Nick and I love doing scenes together. We have a really good time and there’s a lot of banter,” Soffer commented noting that he’s hopeful we’ll see the brother’s dynamic explored through the engagement storyline.

For the latest Chicago PD season 9 spoilers and news, plus more on the entire series, follow the Chicago PD category at One Chicago Center.