"He loves that Smithers isn't using him to get ahead in the fashion world," hints exec producer Matt Selman.

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Year after year after year, The Simpsons played with the idea that Waylon Smithers had an inexplicable, inextricable crush on his boss, Mr. Burns. In 2016, Smithers finally found the courage to split from the tyrannical tycoon (well, temporarily), and explore a requited romantic connection (alas, temporarily). Now, Mr. Burns' overly loyal assistant is getting his biggest shot at love yet.

In the Nov. 21 episode of the animated Fox comedy, titled "Portrait of a Lackey on Fire," Smithers will blissfully enter a relationship with billionaire fashion designer and tart-tongued America's Got Fabric judge Michael De Graaf, who's voiced by Alias alum Victor Garber.

"He's charming and down to earth, and he loves that Smithers isn't using him to get ahead in the fashion world," executive producer Matt Selman tells EW. "Smithers doesn't know anything about fashion. Smithers is a smart, hardworking, intelligent guy. Michael is tired of people from the New York fashion scene where everyone has an agenda. He wants that middle-America regular guy who isn't about status and fashion stuff."

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Smithers and his new boyfriend Michael De Graaf (played by Victor Garber) on 'The Simpsons.'
| Credit: 20th Television/The Simpsons

In season 27's low-key coming-out episode, "The Burns Cage," Homer hosted a bunch of eligible bachelors in his home for Smithers to scope out, and Smithers fell for Julio, the Birdcage-adjacent character voiced by Hank Azaria. The pair were serious enough to get a fishing license and even jetted off to Cuba, though the fling ended when it became clear that Smithers couldn't quite quit Mr. Burns. Five-and-a-half years later, the timing felt right for a new romance.

"We thought, 'His love life is kind of a blank slate at this point," notes Selman. "The show has moved away from him being completely obsessed with Mr. Burns all the time. So it feels a little bit like Smithers is like, 'Who am I going to be with?'"

"Portrait of a Lackey on Fire" truly puts the hearts in Smithers' eyes: he finds himself swept away by Michael (with the help of Christine Baranski and ABBA's "Dancing Queen"), and the two form a promising power couple. But aspects of Michael's fashion empire will prove to be problematic, a concept that appealed to Simpsons writer-producer Rob LaZebnik and his son, Johnny, with whom he wrote the episode. (The elder LaZebnik had previously penned "The Burns Cage" as a loving nod to Johnny.)

You can see what possibilities await Smithers in this exclusive clip from the episode, which airs next Sunday. This Sunday, The Simpsons unveils the second part of "A Serious Flanders," which sends up the world of premium prestige dramas.

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