When Taylor Henry was five years old, she knew her mom had a sparkly crown. And when she went grocery shopping with her mother, she would overhear people say things like, “Oh, my gosh, it’s Heather!” Taylor concluded that she must be the daughter of a Disney princess. When she asked if that was true, Taylor’s mother—Heather French Henry, Miss America 2000—replied, “Close, but no.”

Taylor, now 17, laughs at her younger self. She still loves Disney and her mom, but she has a different understanding of what that crown means. “My mom was Miss America,” she says. “But what matters is that she’s a hard-working individual who works with our nation’s veterans.”

I can relate to Taylor, as I’m also the daughter of a Miss America. My mom is Pam Eldred, Miss America 1970, who represented my home state of Michigan when she won the title. I never likened my mom to a Disney princess, but I definitely knew her crowns were important—they occupied an entire row of a bookshelf in my childhood home—and that the grocery store was a fraught space. Mom was careful never to go shopping “without her face on” because so many people would recognize her.

Despite the public’s perception of pageants, winning the Miss America crown remains a unique achievement. Since the first winner was named in 1921, only 93 women have had the title. But the Miss America daughters club is even more exclusive, as just over half of the winners have had daughters.

I’ve often wondered if my experience growing up as the daughter of a Miss America was unique, so I reached out to two dozen other daughters of past winners. Some of them are tweens, while others are in their late 60s. We’re spread out geographically, and we’ve chosen a variety of career paths, from athlete and attorney to Broadway performer, journalist, teacher, and mom ourselves.

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The meaning of being a member of the Miss America daughters club has changed over the decades as the cultural power of the pageant itself has waned. But it wasn’t always that way. Carol Koplan’s mother, Rosemary LaPlanche, was Miss America 1941. 

The earliest Miss America daughter with whom I spoke, Carol grew up in California where her mother had a movie studio contract and her father produced and directed television shows (her mom was Miss Studio City before becoming Miss California). 

According to Carol, “Well, [being Miss America] was different then because there was only one major pageant—they didn’t have Miss Universe at that time, and all the other pageants…. [Mom] was a celebrity, on the war bond tour, and in all the soldiers’ lockers.”

Carol’s experience contrasts with that of Lynlee Bell, who at 11 years old is the youngest Miss America daughter with whom I spoke. Her mom is Debbye Turner Bell, 1990’s winner, and only the second Black woman to win the title. When Lynlee’s friends at school found out her mom had been Miss America, they asked, “What’s that?” “Nobody really had any interest or knew what [Miss America] was,” she says

While public interest in Miss America has declined over time, the sense of camaraderie within generations of its daughters remains strong. Stacy Sempier is the daughter of Evelyn Ay Sempier, Miss America 1954. She believes that there’s “an immediate connection between Miss America daughters because we have had people ask us the same questions, about the year our moms won, if we still have the crown, what her talent was. I think that’s a lovely legacy of shared experience on our part as daughters.” 

Stacy’s godmother is Lee Meriwether, Miss America 1955, and she grew up thinking of Meriwether’s daughter, Lesley Aletter, as her godsister.

Ava Johnson, 15, whose mom is Nicole Johnson (Miss America 1999), and Victoria Ebner, 12, whose mom is Katie Harman Ebner (Miss America 2002), have forged a friendship despite living on different coasts of the country. In 2016 they met up at Disneyland when Nicole Johnson was speaking in California at a PADRE Foundation event. (PADRE stands for Pediatrics-Adolescent Diabetes Research Education; when she was Miss America, Johnson’s platform issue was diabetes awareness, as she lives with type 1 diabetes and competed while wearing an insulin pump.) Ava and Victoria have maintained their relationship via text. 

The first fellow member of the Miss America daughters club I ever met was Vandy Scoates. Vandy’s mom is Miss America 1965, Vonda Kay Van Dyke. Vandy and I connected when our moms took us to the 70^th anniversary of the Miss America Pageant. We were both only children of former winners, and I remember feeling an immediate kinship with Vandy. We were just a year apart in age so it was easy to hang out as our moms signed autographs and took pictures with fans. 

“When I started getting older, I started realizing how queer I really am,” Lovato says, beaming. “This past year I was engaged to a man, and when it didn’t work, I was like, This is a huge sign. I thought I was going to spend my life with someone. Now that I wasn’t going to, I felt this sense of relief that I could live my truth.”

Like many single 20-somethings, she’s exploring this terrain through casual dating. And in this moment, Lovato says, she feels “too queer” to be with a cis man.

“I hooked up with a girl and was like, ‘I like this a lot more.’ It felt better. It felt right,” she says. “Some of the guys I was hanging out with—when it would come time to be sexual or intimate, I would have this kind of visceral reaction. Like, ‘I just don’t want to put my mouth there.’ It wasn’t even based on the person it was with. I just found myself really appreciating the friendships of those people more than the romance, and I didn’t want the romance from anybody of the opposite sex.”

Frankly, it’s taken Lovato a minute to want romance in general. The new documentary tracks that aforementioned 2020 relationship from engagement to breakup; when things ended, Lovato found herself questioning if she’d ever be able to open up to someone else again.

“Because I denied my intuition of all the red flags that had popped up, I had no one else to blame but myself,” she says. “So I was like, ‘How am I ever going to trust again?’ But really, I was like, ‘Bitch, you should have trusted yourself. If you had trusted yourself, you wouldn’t have ended up in this position.’”

Once Lovato stopped seeing herself as the victim of that situation, she was able to move forward. “My heart is pretty open,” she says. “I’m very much listening to my intuition, and that’s not to say my boundaries or my guard is up. It’s just saying my ears are perked a little higher and my eyes are open a little wider.”

As our 70-minute Zoom call ends, Lovato’s song “I Love Me” instantly pops into my head. “I wonder when ‘I love me’ is enough?” she asks herself over and over in the chorus, determined to find an answer. And it seems she’s found one—but it encompasses more than just loving herself. She’s now checking in with herself. Showing up for herself. Blocking out the noise and following her instincts.

Whether it’s building her dream cloud room or reframing her approach to sobriety, Demi Lovato’s path is finally, completely her own. “Nothing people say or do is going to really change the way I live,” she says. For the first time ever, she’s home.

Christopher Rosa is the entertainment editor at Glamour. Follow him on Twitter and Instagram.

Electric. That’s how Glamour staff members past and present describe our annual Women of the Year awards, which celebrated its 30th anniversary in 2020. When the event started in 1990, then editor in chief Ruth Whitney envisioned WOTY—as we lovingly call it—as a network of high-achieving women coming together to inspire others to reach their goals, and that spirit has remained in the decades following.

Some examples of this electricity: In 1992, when Anita Hill was given a special tribute in a year that also honored Women of the Year Hillary Rodham Clinton, Katie Couric, Whoopi Goldberg, and Jackie Joyner-Kersee. Or in 2013, when Lady Gaga, Malala Yousafzai, and Barbra Streisand were all in the same room. And in 2018, when Kamala Harris, Chrissy Teigen, and Viola Davis were among those celebrated.

Women of the Year has always been a rare opportunity for titans and trailblazers across industries to meet and motivate each other (and you!) with their words. You can read all about this in our book Glamour: 30 Years of Women Who Have Reshaped the World, available now, which highlights some of our favorite WOTY speeches, quotes, and history.

Here, we look back at the moments and honorees who have made Glamour’s Women of the Year an event that makes us not only proud to painstakingly plan and produce, but proud to be women. Each memory and anecdote represents everything the annual event stands for: enrichment, empowerment, and yes, glamour. 

1990

The first Women of the Year ceremony was held in New York City at the iconic Rainbow Room, perched 65 floors above Rockefeller Center. Among the honorees that November was Children’s Defense Fund founder Marian Wright Edelman, who said in her moving speech, “If you don’t like the way the world is, you change it.”

Following the year’s success of feature film Dick Tracy and pop anthem “Like a Prayer,” Madonna was selected to be the magazine’s first WOTY cover star. Glamour editor-in-chief Ruth Whitney praised the icon at the event, telling the crowd, “While everyone’s a celebrity for 15 minutes and media stars come and go, Madonna is still getting what she wanted, still on center stage, still top banana, still commander in chief of her own wildly successful enterprise.”

Women of the Year was never considered by my mother to be a once-a-year event. She wanted to create a network of impressive women who would continue the connections they made at those awards over time. It’s why she would invite past winners back—and many did return. If not every year, then as often as possible. —Philip Whitney, son of the late Ruth Whitney, former editor in chief of Glamour, 1967–1998

We all know how much you should tip a server in a restaurant—18 to 20 percent. But there’s less clarity on how much to tip for food delivery. In a restaurant, waiters bring you your food, often offer witty banter, and can tell you which blend of white will go best with your swordfish. But what about for the people who are responsible for getting food to your door when you order in? Like a Grubhub or Seamless driver?

As a result of the pandemic, our reliance on food delivery drivers has skyrocketed. When DoorDash filed for an IPO last month, the company reported almost 2 billion dollars in revenue over the course of nine months. Unsurprisingly when much of the country was on lockdown, coping (while also supporting local restaurants that were facing closure) came in the form of takeout. 

While they might not refill your water glass throughout your meal, they’re still always there to bring you a bagel in a snowstorm or a cocktail for your quarantine party of one.

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So do the restaurant rules still apply when your food is brought to your door, not the table? Absolutely. Glamour spoke with Grubhub drivers across the country for their recommendations. Read on for their best delivery-service tipping advice. 

How Much Grubhub Delivery Drivers Actually Earn

Unlike waiters, most of these delivery workers aren’t paid by the restaurants outright. They’re paid by Grubhub—and it’s not based on the size or price of the order. “Grubhub has a $3.50 base [depending on location], plus mileage, any bonuses they’re offering, and tip,” says Curtis, who delivers for Grubhub in Denver. While actual fees can vary based on the city or state you drive in, an anonymous driver in Rochester, New York, shared that he gets paid 50 cents a mile. But it’s important to note, he says, that “we don’t get paid from where we are to the restaurant. We only get paid from where we are to the diner, so we can drive up to 20 minutes sometimes to pick up the food that we’re not getting paid for.”

But how do tips factor in? Because Grubhub actually accounts for tips in their payment algorithm, they matter a lot. For John William, a driver in Pennsylvania, “about 50 percent of my weekly earnings is from my tips.” So when you go to tip your delivery driver, remember that it’s a huge portion of their overall pay.

They Have Fees You’d Never Think Of

Grubhub drivers don’t simply walk away with the full fee they’re earning. Much like those working for ride-share companies, the majority of a Grubhub driver’s work is done in their own car. So a portion of their paycheck goes back to gas and overall maintenance on their vehicle. Curtis in Denver estimates that he puts 12 percent of his paycheck back into his truck on things like “new tires, oil changes—which can cost up to $25—or needing to have my brakes redone.” And that’s without gas, which can cost upwards of $50 a week, depending the car.

This was a different time, one that was about the perfect body not about body positivity. We were in the business of aspiration and perfection and a type of beauty that you had to strive for. As models, we were supposed to represent this ideal of beauty—I guess this one tiny thing didn’t fit. It does make you feel like, “Am I not good enough?” Throughout my career, people have retouched my belly over and over sending the message “that’s no good—we’re going to hide it.” They didn’t feel like it was the perfect image and it made this tiny imperfection bigger in my head.

Growing up, I was always insecure about my body because I stood out. I had these big teeth and I was taller than all the girls and all the boys and had these skinny limbs where everyone else seemed to have curves. When you’re that young and your body is at all different, you don’t really know how to work with it, how to make it your own—you need coaching, you need guidance.

When I started working with photographers at 15, I was faced with all my fears and things I was so insecure and shy about. But I got that guidance. It was like, “No, you have a beautiful smile. Smile! We want you to smile.” Then they said, “You have good long legs. You should be showing them off and wearing short skirts.” I was like, “Really? Me?” At that age, it gave me a lot of confidence to embrace my body. It made me feel really good. It really meant a lot to me. So when that same industry told me this specific part of my body was something to be hidden, I believed them.

Now we’re in a different time in the fashion industry that’s all about embracing who we are and the imperfections that make us beautiful. My third pregnancy has given me the opportunity to finally feel free in my body. This is a vulnerable time, an intimate time, for all of us. We’re all at home with ourselves with time to reflect on the things that are important—especially if you have children. What are you teaching them? What are you passing along? I don’t want to pass on the idea that beauty means perfection.

Personally, I love what happens to my body during pregnancy. It’s a beautiful, feminine, sensual time. When I give birth and when I’m pregnant, I really feel like a woman. It’s like, “Wow. I can do that. I’m so strong. I pushed this, I carried this, I’m breastfeeding this, I’m giving this person life.” It’s a Wonder Woman feeling. And it’s your right to enjoy that. Celebrate it. Document it. Frame it.

I’m blessed that I am able to get pregnant, and that I get to do this for the third time—maybe my last time—so I wanted to take some pregnancy photos. I wanted them to be intimate, personal, shot in my home. It was my clothes. It was how I wanted to be photographed. And it was how I wanted to be seen.