What 'Zoey's Extraordinary Playlist' Gets Right About Its Main Love Triangle (Exclusive)

Creator Austin Winsberg has a simple reason why the musical drama is the antidote to social distancing blues. Plus, see a first look!

In uncertain times, the delightfully vibrant and joy-filled musical drama Zoey's Extraordinary Playlist is the antidote to your quarantine blues. For creator Austin Winsberg, whose real life the series takes inspiration from, there may be a simple answer to why: People are in need of happy right now. 

"I think that because the show is upbeat, and comedic at times, and joyful, and really about compassion and empathy, some of those ideas are resonating with people right now," Winsberg tells ET ahead of Sunday's episode. "Maybe there is mood for fare that isn't as heavy or dark, even though we have dramatic and emotional moments in the show. Maybe there's an emotional catharsis in the show too for people."

Winsberg, who lost his father to the same rare degenerative brain disease Zoey's father, Mitch, has, noted that viewer response to the first nine episodes of the season has been varying and heartfelt. For the uninitiated, the one-hour musical drama follows 20-something tech coder Zoey (Jane Levy), who's struggling with the reality that her dad is dying and can hear everyone's true feelings through song. Compounding her anxiety and neuroses is her physical attraction to Simon (John Clarence Stewart), a fellow co-worker, and her best friend, Max (Skylar Astin), who wants to be more than just movie night pals. 

"I read a lot of tweets saying how much the show means to them and that they laugh and cry," he recalls. "I get a lot of messages from people who have family members who have suffered with some kind of neurological disease or they have long-term illnesses in the family that they've had to deal with. A lot of comments about how people feel like we're doing an accurate portrayal of that."

It's helpful then that the featured music, often a gateway to bridging differences, "is connecting with people," Winsberg says. The series has staged ambitious song-and-dance routines to The Proclaimers' "I'm Gonna Be (500 Miles)," Gnarls Barkley's "Crazy," Shawn Mendes' "If I Can't Have You," Rachel Platten's "Fight Song" and on Sunday's episode, Brandy and Monica's "The Boy Is Mine," to name just a few. "Hopefully, people are coming at it from different perspectives and points of view, and finding things that they're responding to."

When Zoey's returns this weekend, the complicated love triangle between Zoey, now ex-co-worker Max and newly single Simon gets even messier somehow. Seriously, just watch Max and Simon dueting with a cover of Whitesnake's '80s anthem, "Here I Go Again," in ET's exclusive sneak peek above, and you'll understand what we mean. 

When the series introduced the idea of Team Max versus Team Simon in the third episode, it was designed to convey to the viewer that, yes, there is a central love triangle brewing. But not the conventional kind where there's often a clear "better" choice. As it's become apparent, there is no easy answer to the question of who Zoey should end up with: Max or Simon. That is exactly the point. "I think people have really taken to that," Winsberg says with a laugh. "There's a lot of very strong opinions and a lot of things that are going on in these relationships. I don't know if I was quite prepared for that level of that engagement on the relationship side of it."

The consequence of Zoey and Simon's spur-of-the-moment kiss after her very revealing performance of Cheap Trick's "I Want You to Want Me" in the glitch episode comes back in a big way in Sunday's upcoming hour, which explores a different side of grief: anger. Zoey and Simon find themselves in a situation where they're forced to air out all their deep-rooted emotions and vulnerabilities.

"Simon is the character we've used for the grief connection and grief bonding over the course of the season. I think he is somebody who is stuck in many ways and spends a lot of time looking backwards, and he has a hard time letting go of what happened to his dad," Winsberg says. "He's got a lot of emotion in his own anger built into his father's suicide. I think that his own emotional turmoil is part of what contributed to his breakup with Jessica. He proposed to her right around the time after his father died. And I think he was looking for a connection where maybe he wasn't ready and she wasn't ready."


"Zoey has seen a lot of what this looking backwards has done. We have a song in episode 10 that really highlights Simon's inability to move forward," he teases. "By showing him stuck in this way and by Zoey being angry in the episode, it was kind of the perfect [moment] for them to have this cathartic emotional fight where they put a lot of stuff on the table that maybe they weren't completely saying."

And with Max moving up to the sixth floor to work at a rival tech company, headed up by Joan's nemesis, Ava Price (Hamilton's Renee Elise Goldsberry), it'll put even more distance between him and Zoey.

"Max is angry at Zoey. He feels like he's been there for her and supported her, and he feels betrayed by her in certain ways. And I think he's frustrated that even though she sings 'I'm Yours,' which is a love song, she still has these other feelings for Simon. That's really hard for him," Winsberg says. "By going up to the sixth floor, he is trying to assert some of his own independence from Zoey and find his own strength outside of this relationship."

"He does a couple of things in episodes nine and 10 that are a little bit more petty or a little bit more reactive emotionally because he is an emotional person and he's reacting to feeling slighted by Zoey and maybe taking it out on her in the wrong ways," he adds. "But it's how he's dealing with expressing himself by being so vulnerable, by telling her that he loved her and not getting the response [he wanted] from her. He's struggling with what kind of relationship he wants with Zoey, and I think he's being a little punitive about it at the same time."

As the actors tell it, it was imperative that they treat the Zoey-Max-Simon dance with a level of care and respect. Translation: See them as living, breathing human beings who make ill-timed decisions (see: Simon dropping by Zoey's place late at night), grand pronouncements (see: Max's flash mob declaration of love) and spontaneous, life-altering moves (see: Simon and Jessica's abrupt breakup).

"John [Clarence Stewart] and I talk about this all the time and never wanting to make it feel like a competition or a choice. Because that doesn't only preserve our characters, but it really protects Zoey. Zoey is nobody's prize and she's nobody's to claim or win over," Astin told ET recently. "There are scenes that Simon and Max have down the line and they have some difficult conversations." 

The Pitch Perfect alum acknowledged that there could have been an easy path for him and Stewart to approach the "mano-a-mano" scenes. "There's an obvious way to play all those scenes; they can be sizing each other up, looking at each other up and down, a game-on type of mentality. John and I have never seen it that way," Astin explained. "At the end of the day, John and I always want to maintain a real level of respect with these two men."

Levy shares similar sentiments, going so far as to defend her character's sometimes questionable moves when it comes to navigating those murky romantic waters. 

"What I like is that, in my opinion -- Jane, the actor who plays Zoey, looking from the outside in -- I'm like, 'OK, Zoey's feelings are 100 percent human and valid,'" she told ET recently. "Everyone is allowed to have sexual feelings towards a co-worker, everyone is allowed to have a deep-down love for their best friend and not only are they allowed, that is just so wildly normal."

"What's great about the show is Zoey's like, 'Sure, I have those feelings. I didn't mean to tell you them, leave me alone. My dad's dying, I don't have to pledge my allegiance to either one of you. I'm not doing anything wrong or sneaky. These are my feelings and I've never promised either of you that I could be anything more than a friend with emotional problems,'" Levy added. "She's been very clear. And I like that it just feels real to me, and it's not gendered, and I don't feel like we're playing out any stereotypes about women and men, or social gendered [roles]... I like that about it because I think Zoey's totally in the right."

Complications aside, at its core Zoey's Extraordinary Playlist is a show rooted in family and the grief that goes along with the impending loss of a loved one. But, it's a fun escape to engage in friendly arguments every Sunday night over who Zoey is most compatible with. We'll just have to wait a little bit longer to find out the answer, if there ever is one.

Zoey's Extraordinary Playlist airs Sundays at 9 p.m. ET/PT on NBC.

To stay up to date on breaking TV news, sign up for ET's daily newsletter.