What To Expect When You’re Esther Povitsky

Sitting in a packed theater on a rainy night to watch people perform still feels special, and when comedian Esther Povitsky comes out on stage on this particular night in Portland, Oregon, the crowd goes nuts. She is wearing baggy jeans, sneakers, and what she later ID's as a Skims underneath a T-shirt (“I hate myself”). She looks like your kid sister who happens to be preternaturally adorable. And also in her third trimester of pregnancy.

Whether it’s from podcasts or TikTok or her various other projects, everyone here seems to know Povitsky, or feels like they do, and they want her to know how much they love her. “You’re so cute!” “You're sexy!” “How is pregnancy?” they shout. This is anti-heckling, and Povitsky welcomes the back and forth. “Are you scared of giving birth?” someone asks near the end of her set. “Yes, I’m terrified. It’s all I think about.” Next question. Someone shouts that she will be a great mom, and she doesn’t miss a beat: “Thank you. But like what do you base that off of?” She’s joking but also she seems to genuinely want to know.

Povitsky is on the precipice of a lot of things in her life right now. Drugstore June, her first feature-length movie, which she co-wrote and starred in, has just premiered. Povitsky is also about to give birth to her first child with her partner, Dave King, an actor and writer. Though she has been performing in comedy clubs on and off for the last 15 years, she’s 35 weeks pregnant, and this might be one of her last nights on a stage for a while.

That she’s physically uncomfortable is something she makes perfectly clear, but she’s willing to talk about the emotional discomfort, too. Povitsky’s ability to acknowledge the uncertainty of life — and by this I don’t just mean impending motherhood and artistic risk, but the everyday uncertainty of being alive — is part of what makes her so captivating. She’s a cynical romantic, I think, and this is the kind of moment she’s made for.

June isn’t an easy movie to describe, but Povitsky takes a stab at it anyway: “It’s kind of about me stalking my high school ex. Played by Haley Joel Osment. And I work in a pharmacy, the pharmacy gets robbed, and I’m just an idiot and try to solve the robbery because I’m stupid. And very unlikable. And kind of a bad person. No, it’s good.”

She’s right — the movie is goofy and glorious and a little unhinged. I would not call June a bad person so much as a deluded romantic and, sure, a bit of a narcissist, and OK, a brat. But a lovable brat. You root for her.

Povitsky, as I’m relieved to discover when we talk after her show, is as funny and charismatic as her fictional avatar, but wiser and less petulant. When I ask her what it’s like to put out a movie right now, “in these times,” she laughs and says she has no idea, but clearly she’s onto something: The indie film was set to open in three cities — New York, L.A., and Austin, Texas — but since we spoke, dozens of showings have been added across the country.

I tell her that I was struck by what a specific world the movie creates — an off-kilter, grimy yet glamorous version of our current one — and what a clear point of view it has. It nails crucial details about the way we live now, down to the uptalk lilt on Internet videos, the hopelessness, the weed stores, the dead-end jobs, the sprinkles.

Povitsky has honed her sensibility through a very specific, very contemporary comedy pipeline: from podcasts (myriad, but most recently Trash Tuesday) and TikToks (popular topics include hot girl shit, pregnantly complaints, comedy sets, and overnight oats) to a 2018 Freeform comedy series (Alone Together) about trying to make it in show business, produced by Lonely Island, and a comedy special, Hot for My Name, which aired on Comedy Central in 2020.

Despite all that experience, the prospect of writing her first feature filled her with self-doubt. “Insecurity will get in your way. And that’s what I think was happening with me for so long with so many things.” She credits her writing partner, Nicholaus Goossen, who is also Drugstore June’s director, with pushing her. “I keep telling people, ‘You need a tall, confident man in your circle,’” Povitsky tells me wryly, “because through the whole process, I was like, ‘Nick, no one’s going to make this movie. Why are we doing this? No one wants this. I am a nobody. Stop.’ And he would just be like, ‘We’re making it. We’re doing it.’ And he was right.”

“This is such new territory in life, and I cannot believe everyone has an extremely strong different opinion.”

And now Povitsky is 36 years old, and everything is happening at once. Her longtime partner, King, is 45, and very happy about her pregnancy. “I’m basically doing a favor for an old man,” she jokes. In seriousness, Povitsky went back and forth a lot on whether she would have kids, partly because she has a history of pregnancy loss, something she references in her standup in a way that feels generous and heartbreaking and totally normal, all at once. (She notes that her miscarriage joke — “They can’t take that away for us, can they girls?” — did not get many laughs in Texas.) Ultimately, her curiosity won out. “I was like, ‘I’m going to try to do this at least once.’ And now I am realizing, as much as I want to think I'm dipping my toe in, no, this is a full-blown commitment. But in my head, I’m like, ‘If I just have one, it’s going to be so easy.’”

She insists she won’t change everything about her lifestyle once the baby comes. She had a mom whose “whole life” was about wanting and then raising kids. She tells me that her mother gave birth to her in one hour with no medication and breastfed her until she was 3 and a half. “I was never away from this woman,” says Povitsky, not without tenderness. “I’m like, ‘I know you’re my mom, but we’re so different.’”

(I feel I must insert here that in Drugstore June, June's overbearing but supportive mother is played by Beverly D’Angelo, and she is iconic and divine, especially when vamping in front of the ring light during June’s Insta lives.)

Maybe because I first encountered Povitsky rattling off “hot girl” beauty products in a remarkably deadpan tone of voice on Instagram, I want to know what the hot mom scene in Los Angeles is like, especially in her women-in-comedy milieu. “I feel like most L.A. moms I know, or comedian moms, have the same approach to motherhood that I have, which is ‘I’m doing what I can to get by,’” she tells me. “It’s like ‘Do formula. It’s just good. If it was really that bad, we’d know.’”

For an extremely online millennial woman, she is refreshingly laid-back about the kind of personal decisions that can turn into no-win parenting debates: “My thing is I’ll try to breastfeed. If I can’t, I am not going to feel shame. I am not going to feel guilt.” Easier said than done, I think but don’t say, because even hearing her say she is trying to be open to how it actually feels in the moment, for her and her baby, rather than what a good mother is supposed to do, strikes me as both wise and refreshing — very un-June-like.

“Usually I kind of know who to listen to, but this time I don’t know anything.”

“But who knows?” Povitsky adds, “Maybe it’ll happen, and I’ll breastfeed, and I’ll be like, ‘Oh, my God, this is amazing.’ I’ve always had fantasies about breastfeeding my dog, so I am like, ‘Maybe it will be that wonderful thing that I like.’”

We marvel at how quickly cultural expectations around parenting can change, even across age groups and micro-generations. When Povitsky’s sister gave birth, for instance, she remembers that her “worst, worst fear” was that she would have to have a C-section. Whereas Povitsky admits to being terrified of the prospect of labor and delivery. “You know what? I don’t know what kind of birth I’m going to have. If we get into the 37-, 38-week point and I’m still feeling really scared about vaginal birth and pushing and labor, I might be like, ‘I’m doing the planned C-section.’”

What is consistent across micro-generations is the onslaught of advice, regardless of medium. “This is such new territory in life, and I cannot believe everyone has an extremely strong different opinion,” she says. “I don’t know who to trust. Do I trust my doctor, my best friend, my sister, my mom, the famous people?” (Anyone but the famous people, I want to say.) “Usually I kind of know who to listen to, but this time I don’t know anything.”

This is the thing that worries her the most — that she has no idea how she’s going to feel. “It’s almost like when you’re in elementary school and you’re like, ‘I’m going to junior high next year. I have no idea what it’s going to be like to have my own locker and to go from class to class.’ That’s how I feel about having a baby. I’m like, ‘Am I going to be so happy? Am I going to be so sad? Am I going to be addicted to my baby and never want to leave the house?’ Or am I going to be like ‘Get me out of here, I want to spend every dime of my life savings on nannies’? I legit don’t know which one it’s going to be."

She asks me what I think it is going to be like for her, and I am so honored that she thinks I might know. Because on some level, I do: It’s going to be both. It’s going to swing wildly. And that will be the beauty of it — she will still be her, just in this wild new circumstance.

“It’s crazy,” she says, completely sincere. “I can’t picture it. I can’t.”

But, I tell her, and this is what I truly feel, that she is a smart woman who knows herself and she will know what to do when the time comes.

“That is a really nice positive benefit,” she mentions, “the instant closeness you have with other women who have done this or are doing it. I feel really close and connected with other people who I otherwise normally would not.” This new feeling of connectedness is what she’s excited by.

That and the new material.

When I think of Povitsky’s gimlet eye unleashed on baby & me yoga or Music Together class, I feel nothing but glee. Yes, the Gen Z girlies need her to tell them what it’s going to be like, but I want to go back in time through her experience, too.

Drugstore June is in select theaters now.