Chicago Med season 4 character preview: Will Halstead

Where we left off

Last season for Will Halstead was almost entirely about Manstead. Chicago Med started the third season with Will confessing his feelings to a returning Natalie—and Natalie responding by telling him she felt the same way. It was a huge moment not just for Will, but for the entire series, since the relationship had been simmering all the way back to the very first episode.

But as the season went on, things started to feel a lot more familiar, in that Will and Natalie were back to butting heads again. They continued to disagree on several cases, and the fighting actually got worse because of their romantic relationship. It was one of the season’s most head-scratching moments when Natalie rightfully called out Will for trying to protect her too much—but then also brought gender into it, saying that he wouldn’t do the same thing for a man.

Natalie went so far as to call time on the relationship, and Chicago Med went back to writing Will as that good guy who makes occasionally dumb life choices. Though they weren’t even broken up, Will got drunk and decided to go home with Connor’s colleague Dr. Maya Frisch (guest star Emma Duncan).

That, of course, only upset his girlfriend further and Frisch didn’t help when in the season finale, she flirted with a now very sober Will in front of Natalie. As Natalie stormed out of the hospital, Will decided that would be a great time to ask her to marry him! But the season ended without revealing her answer, so he (and the audience) have been sitting in suspense all summer.