Grey's Anatomy has always been as much about the relationships as it has been about the medical procedures, which is why it's so refreshing to finally see Maggie get the swoon-worthy romance she deserves. Maggie and Winston's fling on Grey's Anatomy should absolutely turn into a full-time thing because it's been one of the hottest and most satisfying things on the show during this frequently dour season — and the brilliant and beautiful Dr. Pierce deserves a man who's so blatantly into her after all she's been through.
In her six seasons on the medical drama, Maggie's love life has been… rocky, to put it lightly. While she has blazed a trail as Grey Sloan's youngest chief of cardiothoracic surgery and built a supportive family herself with sisters Meredith and Amelia, she hasn't been so lucky in the romance department. Early on, she briefly dated a radiologist named Ethan Boyd. (Remember him? Me neither.) That one fizzled out without going anywhere. Then Maggie had a tryst with Andrew DeLuca; although it was sexy when it was secret, it quickly imploded once they went public with their relationship.
After DeLuca, Maggie turned her romantic attentions to new Grey Sloan surgeon Nathan Riggs — although unfortunately, he was more interested in her half-sister, Meredith. Maggie tried to move on with a hot Tinder date named Clive. That one seemed promising for a hot second… until Clive's wife crashed game night and outed the cheater as a married man. Whoops.
Then there was Jackson. "Jaggie" quickly became one of the least popular couples in Grey's history, thanks to the fact that they had zero chemistry and, oh yeah, were technically step-siblings. (Their parents were married. Yuck.) That misbegotten coupling came to a merciful end earlier this season. Just when it seemed like the show was hinting at a possible reconciliation between Maggie and Jackson, the writers brought Winston in just in the nick of time to save us from a painful Jaggie reunion.
Of course, before fans get too excited about the potential of a Maggie-Winston relationship, we should acknowledge that perhaps the timing isn't ideal, both in the world of the show and the world outside it. Given the dramatic, depressing way the most recent episode ended — with the revelation that Richard Webber is much sicker than anyone knew, what with the hallucinations and the nonsensical presentation — Maggie's about to have her hands full caring for her ailing dad. She already lost her adoptive mother Diane to cancer back in Season 13; having to deal with the decline and (dare I say it?) potential death of her biological father will probably leave Maggie too busy and preoccupied for a new romance.
There's also the small matter that, like many other TV Shows, production on Grey's Anatomy was shut down due to the COVID-19 pandemic. In late March, ABC officially announced that Grey's wouldn't be returning this spring to finish its current 16th season, and that the last episode filmed before the shutdown — April 9's 21st episode, "Put On A Happy Face" — will now serve as Season 16's de facto finale. The remaining four episodes that were planned have been scrapped, and the end of the season is now only two episodes away.
Whatever plans the writers may have had for Maggie and Winston this season will likely have to be put on hold. Neither of the press releases for the April 2 episode nor April 9's finale list guest star Anthony Hill (who portrays Winston), nor do they mention Maggie's tryst with the new character — so it seems unlikely that viewers will see Winston again in Season 16.
It's possible that Winston could make his long-awaited return next fall during Season 17 — but that's a long way away, and given that the shortened season will force the writers to change some of their plans, it's also possible that they'll decide to take Maggie's story in a new direction and viewers never see Winston again. That would definitely be a bummer so, while the writers are breaking the story for Season 17, hopefully they remember the healthy amount of sparks that flew when Maggie and Winston ran into each other this season, and find a way to give Maggie the healthy, loving relationship she so richly deserves after so many failed romantic experiments.