In a new relationship, going makeup-free can feel as vulnerable as getting naked. New York City singles lift the veil on their pre-date and post-romp beauty routines.

In the pilot episode of The Marvelous Mrs. Maisel, Miriam “Midge” Maisel climbs into bed wearing a full face of makeup. After waiting for her husband to fall asleep, she sneaks off to the bathroom to initiate the first phase of her lengthy nighttime routine. She begins by winding her hair in curlers, and then removes her makeup — lashes, lipstick, and all. Finally, she slathers on a heavy face cream, the 1950s equivalent of a modern-day overnight mask.

After adjusting the bedroom blinds, she slips back into bed with her husband. Fast-forward to the early morning: Courtesy of her clever rigging the night before, the sun hits Maisel right in the eyes, waking her up but sparing her spouse, who remains fast asleep. She silently scurries to the bathroom once again, this time to wash her face, remove her curlers, and reapply cosmetics: powder, false lashes, lipstick, perfume. Then it’s back to bed with her husband, who, none the wiser about his wife’s complicated choreography, eventually wakes up to a perfectly made-up Mrs. Maisel.

It’s easy for viewers to dismiss Maisel’s secret, after-dark dance as a hyperbolic representation of the rigid beauty standards that existed during the ’50s. The scene, which aired in 2017, may be more fantasy of a former time than historical account, but there’s something incredibly relatable about the lengths Maisel goes to cultivate the illusion of aesthetic perfection in her husband’s midst. How people make themselves up, and eventually make themselves down, around a new romantic partner helps shed light on ever-evolving beauty norms — and the timelessness of Maisel’s appearance-related anxieties. 

Appearance-based standards — expectations that can influence everything from the way we do our makeup to the way we dress — have always existed, but they’re especially loaded in an era of visual-first dating apps and social media platforms. “Appearances play a big role in the very initial stages of dating, which is why dating apps can be so anxiety-inducing,” says Myisha Battle, a sex and dating coach who runs her own practice, Sex for Life. “People make decisions about who they want to meet based on what they see first. They may not even read the profiles of the folks they're swiping on.

“There's a lot of pressure to show up as the person who you presented yourself to be,” Battle continues. “I have clients who are everyday makeup wearers. [Makeup] becomes a part of who they are and removing it can really feel vulnerable. It’s like getting naked.”

Alexi Alario, co-host of fashion and culture podcast Nymphet Alumni, can’t remember the last time she left the house without makeup. “Once I have makeup on, I’m stepping into my public persona,” she says, explaining that her makeup routine remains the same whether she’s preparing to go to work, see friends, or meet a date. During impromptu sleepovers at a partner’s house, Alario won’t wash her face before bed. Instead, she’ll wake up before him and leave to spare him the sight of her slept-in face. “It takes the pressure off, and it’s a bit of a Cinderella moment for someone to wake up and be like, ‘Wait, where the fuck did you go?’”

Alario, 23, began using cosmetics in her mid-teens. Back then, she experimented with alternative looks. “It didn’t have anything to do with conforming to a beauty standard,” she reflects. “But then I was like, ‘I just want to look hot. I don’t want to wear Lorde-colored dark lipstick.’” 

Alario says that her desire to look “hot” stems from the standards she sets for herself, rather than that of her male partners. “It’s more about my standards of constantly being put together,” she says. “People, especially men, think it’s silly, but I think that silliness is fun.” When asked if the male gaze might unconsciously play into her desire to look coiffed at all times, she admits: “Sometimes I wonder what it would be like to be a boy and not have to do so much to get ready. But I’m in a golden cage with the patriarchy — I'm into it at this point. Because I'm into fashion and beauty, I have fun with it.”

For Kevin Ponce, the stakes are higher. “The goal is always to be unclockable,” she says, using a term to describe transgender women who aren’t recognizably trans. Many transgender women don’t strive to appear unclockable, but “unclockability” can translate to safety and survival in a transphobic world.

Ponce, who began transitioning at age 18, considers makeup a “second skin.” She wears it every day, but doesn’t consider it a chore: “It’s semi-armor,” she explains. “[Makeup] was one of the key points to transitioning,” the 26-year-old continues. “For some people, it may be surgery. For some people, it may be therapy or hormones. For me, it was makeup.… I didn’t come from a family who had a lot of money, who could afford all the surgeries to support my transition.” 

Ponce rarely appears bare-faced in front of the camera and won’t post makeup-free photos on her dating app profiles. “Everyone has their own insecurities,” she says. “I love myself without makeup — I think I look a lot younger — but I don’t like it entirely. There are a lot of things that I still have to work on as I’m continuing with my transition and my journey through womanhood.”

And there’s facial hair to negotiate. If Ponce has a spur-of-the-moment sleepover at a partner’s house, she’ll go to bed with a full face of makeup on “to avoid the morning stubble.” She’ll also get up before her partner to reapply concealer and powder, two products she always keeps in her bag, to cover any inklings of a beard or mustache. In the case of a planned sleepover, she’ll bring a razor and makeup for touch-ups. “I throw on foundation, concealer, powder, and blush as quickly as I possibly can before my partner wakes up.”

Highsnobiety / Anna Chandler

Ponce, who dates cisgender, heterosexual men, has only had one relationship in which she felt comfortable being makeup-free. “It's hard to find someone who’s truly understanding of what it takes to put on this sort of woman regalia,” she says. Worries about her appearance — "Is this person open enough to be accepting and loving towards me, even without the makeup on, even without the lashes?” — are a perpetual presence in her dating life. “The anxiety is always going to be there until there’s a ring on my finger and there’s children in the house. It’s not going to stop until it stops, basically.”

It doesn’t help that memes declaring “Take a girl swimming on a first date” have become fodder for a certain corner of the internet — populated mostly by straight, cis men — inclined to view makeup as a form of “catfishing.” This rhetoric stems from the notion that anything traditionally feminine is deceptive or dishonest, a misogynistic attitude that dates back to the 18th century. A letter published in the April 17, 1711, issue of British newsmagazine The Spectator complained of “Women who do not let their Husbands see their Faces till they are married,” to which the paper responded: “I have indeed very long observed this Evil.… It is hard to speak of these false Fair Ones, without saying something uncomplaisant.”

Makeup is no longer considered evil, by and large, but its link to feminine wiliness lingers. This leaves makeup-wearers, no matter their gender, in a double bind: Everyone is subject to beauty standards, whether it’s clear skin or plump lips — but using cosmetics to better adhere to these standards is often cast as shallow, fake, or “too girly.” 

“[Makeup] has fallen under this sort of feminized work that we downgraded as something done maliciously to deceive, when a lot of people historically have used it to try to conform to beauty standards and beauty norms,” Battle says. “That judgment actually feeds into the anxiety that people have about taking their makeup off.”

Enter the Mrs. Maisel Predicament: to reveal or not reveal one’s beauty routine. Sable Yong, a 36-year-old beauty journalist published in Vogue, The New York Times, and GQ, uses her cosmetic rituals as de facto compatibility tests. To buck the preconceived notions a date might have about her career in beauty, she’s careful to wear pared-down makeup in front of new romantic prospects. Minimal makeup also keeps the conversation from going stale. “I used to wear colorful eyeliner and stuff like that. It would always become a topic of conversation when they didn’t have anything to say.” 

It isn’t until Yong feels “very comfortable” with a partner that she’ll invite him over. “I don’t like sleeping over at boys’ houses because they never have amenities,” she says. “It’s so bad going to their bathrooms and being like, ‘Cool, you don’t even have face wash. This is awful.’” Instead, she’ll break out her entire skincare routine, a 15-to-20-minute affair, in the comfort of her own home. “If we are going to start seriously dating, this will be a thing — I’m micro-pilling him,” she explains. “If a dude is weird about seeing me without makeup, I probably shouldn’t date him.”

Several other women who spoke to Highsnobiety shared Yong’s sentiments, concluding that anyone who judges how and when one applies and eventually removes their makeup is likely an unworthy partner. “This is something that would fall under the category of deal breaker,” Battle agrees. “I think we have gotten to a place in our culture where we think, ‘This person might be good enough if we tweak their clothes, we tweak their hair, we tweak their makeup.’ It’s really damaging to the person.”

While women are often rewarded for altering their appearance with makeup, the opposite is true for Stixx Mathews, beauty editor at Hypebae. “A lot of guys don’t want to date a feminine guy,” he says, acknowledging the fact that makeup is still linked to traditional notions of womanhood and femininity. “It’s a hashtag that goes around on the [dating] apps: ‘no fats, no femmes.’ So if you fall within that category, a lot of guys will ignore you,” the 32-year-old explains. On apps like Grindr and Hinge, Mathews doesn’t post photos of himself in makeup. “There’s more anxiety for me to wear makeup on a date than there is to take it off,” Mathews adds. On first dates with partners he met online, he’ll forgo visible cosmetics; if he does wear makeup in front of a partner, it’s a sign he feels comfortable. “If we make it to a second or third date, I’m coming with a full beat. At this point, you’re getting the full package,” he stipulates.

That said, Mathews’ Southern upbringing is still very much intact. “If I have a guy at my house and I’m getting ready, I disappear. You do not need to be a part of the process, putting on my face,” he says. “You won’t see me take it off, either. You don’t need to know what goes into all of that, mind your business.”

Queer daters like Mathews are subject to different appearance-related expectations than those in straight relationships, which often entail heteronormative gender dynamics. While dating men, Isabelle Yank, 25, has felt less inclined to experiment with makeup. “Guys are very judgemental, like, ‘Oh, you’re wearing dots on your eyes. That’s weird.’” When dating women, however, Yank approaches things differently. “With girls, you can be a little more playful. I don’t have to worry as much if they’re going to like [my makeup].” Yank, who made things official with her girlfriend in early June, describes her current relationship as “less toxic” than her experiences with men. “The gender norms aren’t as rigid since we’re both women, even though we’re very different-presenting women.”

Daphney Poyser, founder of Fern Connections, a matchmaking company catering to LGBTQ+ clients, says, “The expectations are different when you’re talking about straight people versus queer people. The way people dress, the way that people wear their hair, the way that people put their makeup on. People can be a little bit over the top in the hetero world, whereas sometimes in the queer community, it is a lot more relaxed.” That’s not to say that queer people aren’t subject to the same anxieties as straight people. Poyser notes that her clients often worry about appearing a certain way in new relationships, a concern that stems from a universal place: the fear of rejection. “Rejection is the toughest thing that we all face, no matter what age you are, or nationality, or whatever,” she says.

We’d like to think that love is blind, an adage that Netflix’s dating show of the same name puts to the test by making participants “date” without seeing one another. But, as the show has proven time and time again, love has 20/20 vision. “I’ve always spoken about how the world treated me as a man and how the world treats me as a woman,” Ponce says. “Men found me repulsive. A lot of people turned off [from] connecting with me, in terms of a simple, ‘Hello, how are you?’ or even conversing with me at school.” When Ponce began transitioning and wearing makeup, the world seemed to open up. “I found that a lot of men wanted to sit next to me, wanted to talk to me,” she says. “The way [women] naturally look — no makeup, no skincare, no maintenance — it’s just not what society wants.”

She remains unconvinced that women will ever be encouraged to exist in the world “how we enter it,” phrasing that conjures the image of a fig leaf-clad Eve, newly aware of her nakedness after biting into the forbidden fruit: Makeup covers a woman’s unaltered face, a natural state that beauty culture has imbued with shame. It’s no wonder, then, that the decision to don, and shed, our cosmetic fig leaves — or “shield,” as Ponce puts it — can be so fraught. “I’m going to keep giving you a shield that you’re going to respect,” she says. “The chances of someone understanding me or simply communicating with me without the makeup, without the maintenance, is very few and far between.”