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One Chicago’s 5 most WTF relationship moments

Brittany Frederick
Brittany Frederick

One Chicago Center

CHICAGO MED -- "Shaky Ground" Episode 309 -- Pictured: (l-r) Nick Gehlfuss as Will Halstead, Torrey DeVitto as Natalie Manning -- (Photo by: Elizabeth Sisson/NBC)

One Chicago
CHICAGO MED — “Shaky Ground” Episode 309 — Pictured: (l-r) Nick Gehlfuss as Will Halstead, Torrey DeVitto as Natalie Manning — (Photo by: Elizabeth Sisson/NBC)

One Chicago’s relationships have often taken very strange turns. Here are the most WTF ship moments from Chicago Fire, Chicago PD and Chicago Med.

When last night’s episode of Chicago Med revealed that Will Halstead had drunkenly made out with someone who was not his girlfriend, it was a definite WTF moment. But it wasn’t the first, as the ships of One Chicago have experienced several WTF moments recently.

This slideshow is all about those moments. We’re counting down the reveals in relationships from Chicago Med, Chicago Fire and Chicago PD that have left us scratching our heads and wondering what anyone was thinking. Some of the biggest ships in the One Chicago fandom have also had some of the most confusing plot twists—from secrets we didn’t expect them to keep, to breaking up, to even getting together in the first place!

Whether it’s a character like Will doing something stupid, or the writing just not making total sense to us, we’re revisiting the biggest surprises from across the fandom and talking about why they had us shocked, confused, upset or simply heartbroken. We’ll discuss why we thought they didn’t work and what we would’ve done differently, if we would’ve done them at all.

Click through the below slideshow for the 5 most WTF moments from our favorite One Chicago ships, and let us know the moments that have left you confused in the comments.

One Chicago
CHICAGO MED — “Shaky Ground” Episode 309 — Pictured: (l-r) Colin Donnell as Connor Rhodes, Norma Kuhling as Ava Bekker — (Photo by: Elizabeth Sisson/NBC)

5. Connor Rhodes and Ava Bekker’s random kiss

Chicago Med didn’t surprise anyone when Dr. Connor Rhodes (Colin Donnell) and Dr. Ava Bekker (Norma Kuhling) got together. From the moment Ava was flirt-bantering with Connor in the Med season 2 finale, many One Chicago fans predicted she would replace Robin Charles as Connor’s new girlfriend.

So the WTF moment isn’t that Connor and Ava hooked up. It’s how they got to that point which made little sense. At the end of the episode “Folie A Deux,” the two are in the lounge, giving each other a rare compliment and discussing how Dr. Isidore Latham (Ato Essandoh) will need one of them to be his second on an impending conjoined twin surgery.

Then, with absolutely no context whatsoever, they’re kissing—and the next episode “Born This Way” opens with Ava still getting dressed as she walks into Connor’s kitchen.

To say this was an interesting way of introducing the kiss is an understatement. Everyone knew it would happen, but it felt tacked on to a completely unrelated scene, like Chicago Med either just got impatient and threw it in there, or wanted some surprising moment to end “Folie A Deux” on and thought that fit the bill.

We would’ve set this up better. What if they’d kissed after they shared a vulnerable moment in the previous episode “On Shaky Ground”? It would’ve made more sense if Ava had impulsively kissed Connor after he defended her in front of her mentor.

Connor and Ava’s fling ended as quickly as it began, though, so we’ll see if they get a better start when they inevitably rekindle their relationship before the end of the season.

One Chicago
CHICAGO FIRE — “Carry Me” Episode 520 — Pictured: (l-r) Taylor Kinney as Kelly Severide, Miranda Rae Mayo as Stella Kidd — (Photo by: Elizabeth Morris/NBC)

4. Stella Kidd and Kelly Severide’s false start

Stella Kidd (Miranda Rae Mayo) and Kelly Severide (Taylor Kinney) may finally be together now on Chicago Fire, but this wasn’t the first time the show put the idea out there. How Stellaride went in Chicago Fire season 5 definitely qualifies as a WTF moment.

Last season opened with Stella and Severide passionately hooking up, and then progressed with Severide defending Stella from her drunk and violent ex. Okay, that’s a decent way to start a new relationship, and Severide gets bonus points for being the proverbial knight in shining armor.

But then Fire forgot about the relationship almost as quickly as it started. The show introduced Anna Turner (Charlotte Sullivan), and decided to turn Severide’s bone marrow donation into him developing a huge crush on Anna. Meanwhile, not only was Stella single again, but her scenes were mostly supporting Severide in his new relationship, which always felt incredibly awkward to us. Especially when the promos wanted us to think it could be a love triangle.

If we had it to do over again, Stella and Severide would’ve stayed together after their night in last season’s premiere. As much as we love Charlotte Sullivan, there would’ve been nothing wrong with Severide and Anna having a purely platonic relationship. The effect of Severide going through a profound loss would’ve still been there if he had mourned a friend, too.  This ship took the long way around when it didn’t need to.

We’re not entirely comfortable with this ship yet either, because we can still see several ways that Stellaride can get into more trouble. Let’s hope that these two don’t break up after it took so long for them to finally move forward.

One Chicago
CHICAGO MED — “Shaky Ground” Episode 309 — Pictured: (l-r) Nick Gehlfuss as Will Halstead, Torrey DeVitto as Natalie Manning — (Photo by: Elizabeth Sisson/NBC)

3. Will Halstead and Natalie Manning’s “break”

The moment that prompted this list comes in, in the middle of the list because it’s not flattering for either side. While Stellaride and Ava-Connor were just random, the current state of affairs with Chicago Med‘s first couple is making them both look bad.

One Chicago fans rejoiced when Dr. Will Halstead (Nick Gehlfuss) and Dr. Natalie Manning (Torrey DeVitto) finally got together at the start of Chicago Med season 3. Like their colleagues Connor and Ava, the writing was on the wall here, except for Manstead it’d been the whole series coming. At the same time, it was a given that their happiness would not last forever, because that would be too easy.

When the drama arrived, it was two WTF moments making one big WTF moment. First, Natalie angrily told Will that she needed a “break” from him, saying that he was overly protective of her because she was a woman; the way she phrased it made Will sound sexist and felt totally unfair. Now, while they’re on this break, Med has had Will get drunk and make out with Dr. Maya Frisch (guest star Emma Duncan). At least they didn’t have sex, but they may as well have, considering it still infuriated Natalie.

No one’s behavior in this feels in character; the whole thing comes off as relationship drama to have relationship drama, and our frustration is further compounded because there were other, better reasons to give Manstead some hurdles to overcome.

Natalie getting upset with Will for over-protecting her because she’s his girlfriend? Fine, and it’s absolutely right. That’s what he was doing all season. But when she throws in how he wouldn’t do that with Choi or Noah because they’re men, it becomes an issue not about their relationship, but a bigger issue of him seeing women differently, and it’s kind of offensive. Maybe she phrased that badly, but there’s no reason to bring the problem up to that level.

And they’re on a break, not broken up, so why is Will putting his lips on another woman? Okay, we’ll allow that he was drunk and drunk people do stupid stuff—but if he loves Natalie as much as we know he does (having pined after her forever), why does he fall for a woman he’s literally just met, who has no charm whatsoever? Frisch is like Med‘s version of Hope Jacquinot from Fire; she is so obvious, it’s painful. Even drunk Will should know better.

It would’ve been a lot more interesting if Chicago Med focused on the professional conflict that results from Will outranking Natalie, and if it really did bleed into their personal relationship. That’s a great story. Instead, the show’s done a pretty good job of blowing up Manstead with a series of bad choices all around.

One Chicago
CHICAGO FIRE — “Lift Each Other” Episode 507 — Pictured: (l-r) Kara Killmer as Sylvie Brett, Jon Seda as Antonio Dawson — (Photo by: Jean Whiteside/NBC)

2. Sylvie Brett and Antonio Dawson’s multiple break-ups

We’re still not sure why Chicago Fire broke Sylvie Brett (Kara Killmer) and Antonio Dawson (Jon Seda) up in the first place—and they just keep doing it.

One of One Chicago’s rare cross-show pairings that’s stuck, Brettonio was a pleasant surprise until we got to Chicago Fire season 5. An argument between the two that was incited by his ex-wife Laura coming to the firehouse somehow escalated into Antonio and Brett going their own ways. That felt weird enough, but the real WTF moment has come in what’s happened since.

One Chicago has tempted us with Brettonio getting back together this season. But when they finally did, it lasted for just a few episodes before Brett then inexplicably dumped Antonio, saying she didn’t want to wind up having serious feelings for him again. It was another decision that we didn’t quite understand. That made two head-scratching moments.

Since then, we’ve had Antonio sleeping with a guest star, then him and Brett hooking up in car, Brett going through a pregnancy scare, and Antonio going on a blind date with another woman. What was a cute and potential-filled ship has become a muddled mess and we’re not sure if we should keep hoping or just throw up our hands.

It feels like Chicago Fire has consistently made choices with Brettonio that are more to keep drama in the relationship than move it forward. What adds to the issue is that the writers clearly know Brettonio has fans, because they’ve continued to tease the idea of a reconciliation. We would’ve never split them up in the first place, but we’ll settle for them picking a direction and sticking with it. Both characters deserve clarity in their personal lives.

If the writers need some persuasion on this subject, we’ve got our five reasons why Brettonio needs to be fixed.

One Chicago
CHICAGO P.D. — “Last Minute Resistance” Episode 419 — Pictured: (l-r) Sophia Bush as Erin Lindsay, Jesse Lee Soffer as Jay Halstead — (Photo by: Matt Dinerstein/NBC)

1. Jay Halstead, Erin Lindsay and Jay’s ex-wife

The very definition of WTF moment came to us from Chicago PD, when it killed off the show’s central relationship by revealing that Jay Halstead (Jesse Lee Soffer) had a previously unknown ex-wife!

The bewildering Abby turned up in Chicago PD season 4 when she showed up to have Jay sign their divorce papers; audiences were told they’d gotten impulsively married well before he came to Chicago or gotten involved with Erin Lindsay (Sophia Bush). But despite her reason for coming, at the end of her episode Abby was trying to put a move on Jay anyway.

Though Jay showed better judgment than his brother Will and rebuffed Abby’s interest in getting back together, he still went back to the place he shared with Erin and declared that he was moving out so he could work on some personal issues that Chicago PD never made truly clear until this season.

In the interim, Jay and Erin not only broke up—despite the fact that all Jay did was ask for space, not the end of the relationship—but he then decided to propose to Erin, even though at the time they weren’t even a couple any more.

Now, let’s be fair. We know that Chicago PD had to find some way to bring an end to the Linstead ship, because Sophia Bush left the show after season 4. But according to Bush’s comments later, the writers had advance notice she was leaving. And they fumbled this to the point it wrecked the ship instead of just concluding it.

Why pull a random ex-wife out of Jay’s history? How does her return suddenly make him recall issues he needs to deal with? Why does he then not actually deal with them (sans one scene that was deleted and only appeared on YouTube) until next season? And if they’re broken up and he’s got so much stuff to handle, how does he then suddenly decide he needs to marry Erin?

Absolutely nothing about Linstead’s conclusion made sense. It would’ve been perfectly fine, and a lot simpler, if Jay had simply decided to propose to Erin—and she made the tough decision to say no, she loved him but needed to get a fresh start outside of Chicago. Fans would have understood that, and Jay would have, too.

Instead, one of One Chicago’s favorite ships ended badly, and Linstead fans will always have that sour note in their memories, unless Sophia Bush returns to give more closure to their story. It was a wrong turn that should have, and purportedly could have, been avoided—and that’s what makes it the most WTF moment in the history of One Chicago ships.

Next: One Chicago's most stressed characters

What do you think is the biggest WTF moment for any One Chicago relationship? Let us know what you’d put on this list in the comments.

Brittany Frederick

Brittany Frederick

Brittany Frederick is an award-winning entertainment and sports journalist, screenwriter, and novelist. She runs FanSided's One Chicago Center (for NBC's One Chicago franchise) and Precinct TV (for TV crime dramas). Reach her at her official website (brittany-frederick.com) and on Twitter (@tvbrittanyf).