Well, well, well, what do we have here but another taboo office romance on Grey’s Anatomy?
I’m talking, of course, about Dr. Winston Ndugu (Anthony Hill) and Dr. Jules Millin (Adelaide Kane). Their escapades around Grey Sloan remained on the down-low for most of season 22 … until they were spotted by Dr. Ben Warren (Jason George) in the last moments of the finale. We’ll see how their tryst plays out when Grey’s returns, but for now, let’s take a step back and examine this relationship for what it is: an evolution.
Obviously, Juleston whispers — nay, screams — with echoes of the office romance that started it all: the one between Meredith Grey (Ellen Pompeo) and Derek Shepherd (Patrick Dempsey). But a whole 21 years have passed since MerDer, and the Grey’s Anatomy team wisely understood that exploring the boss-and-subordinate trope would, in 2026, require some adjusting.
“I think how long it took for them to get together,” showrunner Meg Marinis told me, “is a testament to how Winston was reluctant to even go down this path because of the power dynamic. They dragged their heels because he didn’t want to be seen as someone who takes advantage of the dynamic, and Jules doesn’t want to be seen as someone who is sleeping with her boss.”
That’s an intentional contrast to standard templates both on Grey’s and television at large; for as long as anyone can remember, characters would hook up first and figure out the repercussions later. Juleston looks like a cultural reset, and here’s why.
Clocking tea on the clock
A whopping 60 percent of adults have had a workplace romance, which makes sense because, I mean, they’re right there. Yet these situationships can lead to complications, including diminished performance and negative perceptions of the company. We’ve seen how these situations are inherently prone to messiness, both on Grey’s and off. Recall, if you will, how Cristina (Sandra Oh) and Burke (Isaiah Washington) conspired to hide his hand tremor in season three to protect his career and went to increasing, and potentially disastrous, lengths to conceal it. Or when Meredith interfered in Derek’s Alzheimer’s study, jeopardizing her career, the trial, the hospital itself, and her marriage in season seven. Off-screen, we all witnessed how a CEO and a company HR director got caught canoodling at a Coldplay concert, turning them into a viral phenomenon and triggering intense scrutiny of their personal lives. Their choices and the resulting consequences for their families were none of our business, but the public’s discovery that a boss and an employee might have been engaged in some, shall we say, inappropriate behavior gets at the heart of why people instinctively view these dynamics with some discomfort. At the bare minimum, these situations prompt one big, awkward question that looms large in the back of everyone’s mind: Shouldn’t y’all be working?
Grey’s has made the complicated office romance part of its DNA from the start, and for good reason. Love, lust, unrequited attraction, and sex all resonate with us on a primal level, and there are only so many ways to put characters in can’t-turn-away entanglements. If there’s one thing Shondaland knows how to do, it’s craft the heck out of a star-crossed lovers sitch, and a boss-and-subordinate pairing remains a solid “Oh, no, they didn’t!” choice. Yet what’s novel about Juleston is their care and deliberation. In the past, characters on Grey’s would hop in bed (or shag in a closet or where medical supplies are stored, etc.) and consider the fallout later. These two put professionalism first in ways that felt fresh for the show and TV at large.
Undoing toxic manhood
Winston, let’s face it, has been…out there as of late. Post-divorce, Ndugu entered a totally understandable nonmonogamous “for the streets” phase, which was, as I said in this chat with Marinis during season 21, good for him! Yet as Hill himself told Shondaland, the normally by-the-book Dr. Ndugu got a little sloppy, eventually giving way to a more deliberate approach. Hence his call to move Jules off his service once the chemistry intensified. It was perhaps a little unfair to treat her like a chess piece, but his choice was in the hope of being and doing good — for her, him, and the hospital at large. We’re all used to — and fatigued by — seeing male characters struggling with their baggage but taking little to no action to fix it; it’s just stuff dumped onto the female partner to have and hold. In 2026, viewers expect romantic stories to, at the very least, not ignore how discourse around sexual harassment, power, consent, and control has fundamentally changed how we see relationships. Seeing this man take responsibility for his own behavior and understand how a dalliance with a subordinate could harm her — instead of being all “Oops, sorry!” — felt like progress. And it’s worth noting that as Jules revealed her plan to freeze her eggs along with Simone (Alexis Floyd), Winston hasn’t once questioned how her decision affects him. Granted, you don’t get a prize for not being a jerk, but his respect for her bodily autonomy and future plans isn’t nothing either.