Does Chicago Med’s Will Halstead deserve better?

Chicago Med season 5 has Dr. Will Halstead in another complicated relationship with Dr. Hannah Asher. Can the show do better for Will than this?

Fans of Chicago Med know that Dr. Will Halstead (Nick Gehlfuss) has never had the best luck with his romantic relationships, but what he’s gotten himself into during Chicago Med season 5 might take the cake.

SPOILER ALERT: This article contains spoilers for Will Halstead’s storyline in the last several episodes of Chicago Med. You can catch up with this week’s episode in our recap.

Viewers probably want to give Will a good shake after he decided to sleep with Dr. Hannah Asher (recurring guest star Jessy Schram), the OB/GYN whose drug addiction he discovered after she turned up at the safe injection site where he worked.

In Wednesday’s episode “Who Should Be The Judge,” Will was continuing to orbit around Hannah; he not only visited her in rehab, but smuggled in medication when he didn’t think she was getting the right course of treatment.

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That didn’t go well, as she thought he was jeopardizing her spot in rehab, and screamed at him to get out. But knowing Chicago Med, that won’t be the end of the story—and what’s already been a hugely frustrating season if you’re a Will Halstead fan.

To recap: Will started the season watching his one-time fiancee Dr. Natalie Manning (Torrey DeVitto) be engaged to Phillip Davis (recurring guest star Ian Harding), then found out Phillip was a sociopath who had lied about Natalie accepting his proposal.

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After Natalie pushed Will away, she eventually came running back to him, but then it was Will’s turn to say that he was better off without her and leave her in tears.

And now Will’s had a rebound fling with Hannah Asher—only after she blackmailed him by threatening to reveal his involvement with the safe injection site if he reported her as an addict. It honestly feels like he needs a relationship intervention.

Let’s face it: Will has never had the best luck or judgment when it comes to romance. Like his brother Jay Halstead (Jesse Lee Soffer), Will leads with his heart, and in a romantic sense that means he pours so much into a relationship, so fast. He also has a tendency to see women for who he wants them to be or what he thinks the relationship can be, not who they are.

His primary relationship has been on-again, off-again with Natalie, and Manstead has been full of problems on both sides. Will was pining for Natalie before Chicago Med even started, and so it’s no wonder that he’s kind of a doormat when it comes to her.

He always wants Natalie, no matter what happens or how she behaves. He’s there when she comes back, he’s thinking of her even when he’s with someone else (sorry, Nina), he’s always somehow on her side (whether it’s worrying about her brain injury or how he seems to get over their arguments a lot faster than she does).

In turn, Will is Natalie’s safe space, and she can always keep coming back to him and be different with him than she is with anyone else. But that doesn’t make their relationship healthy. As Will did finally point out this season, they fight a lot—and it’s usually over ridiculous things like Natalie implying he was sexist or Will drunkenly making out with another doctor.

And when they’ve broken up, which is numerous times by now, it’s always been easy for Natalie to move on whereas Will can never quite let her go. It’s obvious that he has/had her on a pedestal as his one true love, until this season. So it seemed like maybe Will would grow, or just seize a chance to work on himself for a bit.

Then Hannah Asher happened. Chicago Med‘s plotline in itself wasn’t a terrible idea, but when the show made it sexual between the two characters, then it was just more of the same. Once again, here was Will Halstead getting involved with a woman who didn’t treat him that well, and refusing to let go.

At least with Natalie, we know they’ve had history before the show started and we’ve seen them genuinely be happy with each other sometimes. Hannah and Will have only recently met (that we have seen on screen anyway), and most of the time she’s been snippy with him at best and trying to ruin his career at worst.

Again, they’re arguing, and it’s actually worse now because it’s about things that matter like patient health—which makes it all the more frustrating that Will can be so bullish knowing that Hannah’s behavior is wrong, but then in the same episode be holding her hand at Molly’s and by the next week, waking up in her bed.

And even after they’ve had sex, she still doesn’t really seem to care that much about him; she just cares about whether or not he does something to affect her career. Despite that, Will spent this week visiting Hannah in rehab and attempting to help her. She’s done nothing but make his life more difficult except for a one-night stand, and he’s bending over backwards for her.

Will clearly sees something in Hannah that isn’t there, like he’s idealized Natalie before. With both of them, he gets involved and keeps wanting to be in their lives, even when he’s getting nothing in return.

He needs to take a long look at himself, or rather, the Chicago Med writers need to look at how they’re writing him. They’ve had fans on the Manstead roller coaster for four and a half seasons, and then they’ve thrust him into this new relationship that didn’t need to be romantic at all. This would be the time to let him be single, and allow him to grow as a person, not as one half of any pair.

And perhaps in season 6, he can find someone like Nina Shore who wants to pursue him instead of making him do all the work. Maybe that will be a more mature Natalie, or maybe it’s not, but he ought to have a relationship that’s more equal and not just him going zero to 60 and then getting hurt again. It’s time for Will to have a happy ending and get it on his terms, not someone else’s.

For the latest Chicago Med season 5 spoilers and news, plus more on the entire series, follow the Chicago Med category at One Chicago Center.