Timothy Simons knows what it takes to make a good ensemble.
For seven years, the actor played the hilariously repellent Jonah Ryan on Veep, a towering political sycophant with a vernacular so synonymous
with HR violations that getting slapped for saying “eating so much pussy I’m shittin’ clit, son” during a campaign event at an elementary school was just a typical Tuesday afternoon. With a powerhouse cast that included Julia Louis-Dreyfus, Tony Hale, Anna Chumskly, and Reid Scott, the series raked in a whopping 17 Emmy wins during its time on air and made Simons a recognizable face in Hollywood. In the Netflix rom-com series Nobody Wants This, which debuted in 2024, Simons slots easily into another great comedic ensemble. Simons plays Sasha Roklov, the goofy sidekick brother of Adam Brody’s Noah Raklov, a rabbi known for his easy one-liners about marriage and the Jewish faith. But with the recent release of Season Three, Simons has found his character — and himself — in an unexpected transition. Audiences know Simons can make them laugh. Can they believe him as a serious romantic lead?
“There are definitely times in the past where I would have run from this,” Simons says of Sasha’s new storyline. “But we all get older. My main goal is for people to watch something that I’m in and think, ‘I didn’t know he could do that.’ That’s my main fucking goal.”
Four days after the season premiere, on a strikingly sunny Monday in October, Simons meets me for a coffee at a rooftop bar overlooking Hudson River Park. A Los Angeles resident, the 48-year-old is in Manhattan for press and is delighting in some New York-staple activities, which currently include doing a New York Times crossword by hand on the subway and then going to see Louis-Dreyfus in her Broadway show, Other Desert Cities. “I always do it in pen,” he says of the puzzle, moving his newspaper away from the threatening condensation on his glass. “But I know that’s gonna fuck with me come Thursday [when the puzzle gets harder].”
Part of Sasha’s sweet charm clearly comes from Simons himself, a husband and a father of two with close to two decades of marriage under his belt. In Nobody Wants This, audiences meet Sasha in a similar place, happily married to his wife Esther (the winningly caustic Jackie Tohn) and dopily trying to connect with his tween daughter Miriam (Shiloh Bearman). But when Noah starts an ill-advised relationship with sex-and-relationships podcaster Joanne (Kristen Bell), Sasha and Esther’s social lives get thrown into disarray. For Sasha, this means meeting a new foil in Joanne’s sister and podcast co-host Morgan, played by Justine Lupe. While the two start as accomplices to Noah and Joanne’s interfaith hookup, Morgan and Sasha quickly develop an electric chemistry that underlines every interaction. He’s married. She’s a flight risk. And their siblings are in love. What could possibly go wrong?
The duo became fan favorites after the show’s first breakout season. And the discussion about whether a relationship between Sasha and Morgan could survive wasn’t just online. The entire cast often debated the topic in group interviews — even when the writers refused to tell them if there was an eventual plan to get the pair together. The biggest roadblock: Sasha and Esther’s marriage. If that union is successful — and Simons and Tohn do sparkle with a fond affection when they’re onscreen — why end it?
Simons says, counterintuitively, that the lack of information about Sasha’s romantic future actually deepened his onscreen dynamics with both Lupe and Tohn. It allowed chemistry to develop with each woman, while creating the possibility for two versions of Sasha’s life — one where he stays married to Esther and another where he risks it all for the draw of Morgan.
“Whether it’s romantic or physical or not, there is an attraction between [Sasha and Morgan]. We didn’t have to go back and redraw anything to make [their romance] fit,” he says. “I’ve never really viewed myself in any way as a classical romantic lead. It was fun that we were doing a very romantic storyline, but the version of that with two weirdos.”
This might be the first time audiences have really been presented with Simons as a serious romantic option. But after majoring in theater at the University of Maine (his home state), and spending six years in Chicago’s independent theater scene before heading to Hollywood, the actor has the training to be as versatile as needed. That experience is on display this season, where Sasha is tapping into a previously unknown inner life.
While Sasha’s marriage with Esther stagnates, the couple’s separation opens the door for the well-traversed ground of exes who are forced to see their former partners as sexual beings anew — setting up dating profiles, getting makeovers, going on first dates, and developing seemingly new personality traits. Sasha gains not only a spine but a real sense of maturity throughout his romantic journey. And the earnestness he displays becomes increasingly, well, hot. At one point, the sight of his new bachelor pad, with matching furniture, coordinated paint jobs, an uncluttered floor, and a freshly decorated room for his daughter, turns on Esther so much that she practically throws him onto the bed before he’s done talking.
“It’s a romantic comedy, so there’s a clear joke of [Esther being like], ‘You hung up your towel. We’re gonna fuck now,’” Simons says. “But Sasha has such a fear of getting in trouble that he doesn’t take a lot of steps to stand up for himself. He doesn’t take risks. In this [season], he’s adrift. And for the first time in his life, he has to actually take some ownership.”
Sasha’s chemistry with Morgan comes to a head in Episode Seven, when the pair take a trip to New York for Morgan to film an episode of Watch What Happens Live With Andy Cohen and are forced to come face to face with their feelings. First, a helpful hotel employee (a delightful Taylor Dearden sighting) puts the duo in a room with only one bed. Then, Real Housewife Lisa Rinna wears the outfit Morgan had planned — forcing Sasha and Morgan to dash through the streets of New York for a suitable second option. It’s a welcome tonal shift from the chafing domestic back-and-forth between Noah and Joanne, and feels reminiscent of a bygone era of New York-set romances. (The closest parallel might be the quiet, seductive pull of the Girls episode “The Panic in Central Park.”)
Lupe credits much of the onscreen dynamic between Sasha and Morgan to the “innate trust” she and Simons have built as co-stars. “Things show up because of our comfort level with each other that might not be there if we were not so close,” she says. As for Sasha and Morgan’s appeal as a couple, there’s a clear element that stands out to her. “They’d make each other laugh,” she says. Then again, “They would probably be pretty volatile as well,” she says. But that’s not a bad thing. “They show each other things they don’t show to the world at large. There’s a vulnerability that’s been earned between them over the seasons.”
The Nobody Wants This team filmed this season’s penultimate episode last, which Simons said imbued the entire endeavor with a sense of pressure. “Kristen and Adam had a very famous kiss in this show. We all watch that, and we’re like, ‘Oh, my God, their chemistry is amazing! That looks so easy.’ I don’t think that shit’s easy at all,” he says. “I really felt that in the lead-up to this. ‘What if we get there and it doesn’t work?’” There were practical concerns the two had to work out. Simons is six feet six and Lupe is a willowy five feet nine. “We’re limb-forward people,” Simons says. “We were worried about looking like fucking Muppets when we kissed. Luckily, it worked.”
For Lupe, it was “one of the most remarkable acting experiences” she’s ever had. “We got this little shared time just living out our weirdo rom-com fantasy, which is a gift I think both of us doubted we’d ever have, considering we’re both usually cast as the sideline oddballs,” she says. “I could feel the shared understanding of how special it was for both of us.”
In a will-they-won’t-they to rival Noah and Joanne’s tumultuous start, the season ends without a clear consensus on Sasha and Morgan’s future. They’ve finally acted on their feelings for each other, but Sasha turns Morgan down when she tries to start an actual relationship. The scene is a tender and surprisingly heartbreaking moment. “Justine is incredible. For Morgan, she’s able to find, even in this very messy chaotic character, this immense vulnerability,” Simons says. “There were times where even as a performer, looking at Justine’s face, I was just like, ‘Man, we gotta fucking solve this. She’s in a lot of pain. Just say yes!’”
While there’s no news yet on whether a Season Four is in the works for the Netflix series, Simons says the Season Three pivot does have him considering whether romance could be a new avenue for him. Though he’s quick to caveat that his next move isn’t complete and total hottie movie-star domination. “I am old enough to know the boundaries that I live in,” he says.
By way of example, he says, “When I went to see Twisters, it was one of the most incredible things I’ve ever seen. There was a moment where Glen Powell’s wearing a cowboy hat and a white T-shirt and it’s raining a little bit. He comes out of the house and everybody in the audience cheered. Then it cut to his waist and everybody cheered louder. That might not be where I fit in.”
But with a post-Veep career of supporting roles ranging from dystopian series like Station Eleven and The Handmaid’s Tale to Disney’s Percy Jackson series and the action-comedy feature Joy Ride, Simons’ excitement feels less about suddenly realizing people want to see him make out onscreen and more about finally getting the chance to prove he can be more than the comic relief.
“I’m not going to convince anybody that if I come out in a white T-shirt and a cowboy hat in the rain, they should cheer,” Simons says. “But I think there is a version of that that I can fit into. It might just have to be a little bit more offbeat. But I can do anything.”
PRODUCTION CREDITS
Grooming by JESSI BUTTERFIELD
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