I Want What They Once Had: Natasha Lyonne and Fred Armisen

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Photo: Getty Images

Love is a many-splendored thing, especially when you’re gawking at it from the outside. In this column, we’ll be examining the celebrity couples that give us hope for our own romantic futures and trying to learn what we can from their well-documented bonds.

There’s nothing I love more than when two weirdos find love, and that’s exactly what happened in 2014 when Natasha Lyonne and Saturday Night Live alum Fred Armisen started dating. On its surface, the match made perfect sense; they’re both hot oddballs with extremely impressive comedy résumés to their names. (Lyonne, the star and co-creator of Russian Doll, was on Orange Is the New Black when she and Armisen got together.) And while Lyonne and Armisen broke up in 2022, the sketch and improv nerd inside of me still rhapsodizes about the meeting of the minds that their eight-year relationship represented—especially since the two were both on hand for SNL’s 50th-anniversary celebrations this weekend.

If I had to distill the essence of Lyonne and Armisen’s relationship (as I perceive it from my couch, of course) down to a single photo, it would probably be the one below, of Armisen wearing Dracula teeth and Lyonne in full-on bombshell glam at the 2018 Emmy Awards:

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Lyonne and Armisen at the 70th Primetime Emmy Awards in 2018

Photo: Getty Images

Another of my favorite details from the Lyonne-Armisen relationship is the fact that it was comedy goddess Maya Rudolph who introduced them. A 2019 Glamour article spelled out how it all went down, according to Armisen; apparently, he and Rudolph visited Lyonne at her apartment, where they found her chain-smoking in a long silk robe and sunglasses. “I pulled out a copy of [Legs McNeil’s punk oral history] Please Kill Me, autographed it, and was like, ‘Welcome, kid. Fred—what a name. Happy birthday. Enjoy the book.’ He still has it,” Lyonne said.

Unfortunately, even the most bit-heavy relationships have to come to an end at some point. “I had been [in Los Angeles] living with Fred and during COVID,” Lyonne said in a 2022 interview with The Hollywood Reporter. “I honestly think we broke up because I wanted a swimming pool. We love each other just about as much as two people can love each other, and we’re still talking all the time. But Freddy doesn’t like a swimming pool. It might seem like a mundane reason for a breakup, but during that pandemic, you’ve got to get your laps—I’m like Burt Lancaster in The Swimmer.... So that’s the real scandal. I guess I finally am an actual bicoastal.”

Do I actually think that Lyonne and Armisen broke up because of an incompatibility in their preferred form of cardiovascular exercise? No, although that would be extremely LA of them. Then again, Armisen—who married the actor Riki Lindhome in 2022—seems like he might be kind of tough to date long-term (remember his second ex-wife, Elisabeth Moss, saying that “One of the greatest things I heard someone say about [Armisen] is, ‘He’s so great at doing impersonations. But the greatest impersonation he does is that of a normal person’”?), while Lyonne seems like the kind of woman who really, really thrives at being single.

Obviously, I wish nothing but joyful partnership for Lyonne and her current beau, the filmmaker Bryn Mooser, but I can also see her as an 80-year-old woman who swims daily laps, wears a glamorous turban that reads “PROPERTY OF NATASHA LYONNE” in real diamonds, smokes cigarettes from a Holly Golightly–esque holder, and meets a 93-year-old Armisen every Sunday for brunch at the Sunset Tower Hotel so they can trade showbiz gossip over eggs and coffee. Doesn’t that sound nicer than just (ugh) dating?