My Best Friend Moved To Cuba & Transformed In The Most Magical Way

Photo: Getty Images.
Even though we’re 26, a part of me will always see my best friend Hannah in her 11-year-old form — with missing baby teeth, tie-dyed socks, and a long hair wrap. Like any middle schooler, she was a little nerdy and self-conscious. But she was bold. She would ask the embarrassing questions everyone else was thinking, but which no one wanted to say out loud — like “What’s a blow job?”
Hannah and I grew up together. She was the first person to ever do my makeup in middle school and later for senior prom. I don’t have to explain myself to her in the same way I do to new friends in a new city. We get each other. We know each other’s strengths, and we seek to strengthen each other’s weaknesses, despite the geographic distance between us.
Recently, at midnight on her 26th birthday, we FaceTimed. Sitting in my bed with a PBR and 1,700 miles between us, we toasted to our best-friend long-distance relationship. But hearing her voice on the phone and reminiscing about the past doesn’t match up with present-day Hannah. It’s not until I’m sitting next to her, in her apartment in Cuba, that I start to see the woman she has become.
Hannah first traveled to Cuba in 2010 through a study abroad program. For the past five years, she’s been living there, working in tourism and contributing to news outlets like The New York Times and The Wall Street Journal. In her 30-minute voice memos, she described her life to me, but I never considered visiting her. Flights were too expensive, and obtaining a visa sounded complicated. But then, the U.S. and Cuba started opening up their borders, and commercial flights became available. All of a sudden, there was an urgency to go. The plan was to travel to Cuba for two and half weeks, learn about the life of my best friend, and make a series about growing up in Cuba for Millennial, a podcast I host about coming of age.

As I took a cab into Havana, everywhere I looked, there were women and girls flaunting their femininity.

When I land in Santa Clara, Cuba, I was hit with a wave of heat I’ve never felt on the streets of my neighborhood in Portland, ME. It was an instant reminder of how different my life is from Hannah's. As my senses took in the country that has become home to my best friend, I started noticing little things that surprised me.
I was drawn to a young woman working security at the airport. She was wearing a mini skirt, a tight, low-cut shirt, five-inch platform heels, hoop earrings, and full makeup. I felt like I was passing through a scene in a telenovela, but I had to remind myself that in Cuba, this is real life. Her attire wasn’t what I expected a professional to wear, but she dressed with an air of confidence that drew me in. It was like she’d worn that outfit most of her life.
As I took a cab into Havana, everywhere I looked, there were women and girls flaunting their femininity. It was illustrated in the short-skirt-wearing secondary-school girls, the grandmothers standing in doorways with open cleavage, and the curvy women in see-through blouses. In the U.S., their bodies would be judged, but here they seemed to blend in — a freedom that’s so unfamiliar to me.
When they walk, there’s a strength in their strut, as if they're saying, “I have nothing to hide and nothing to be ashamed of.” Maybe this is what it means to be a woman in Cuba.
When I first saw Hannah, I noticed she’d acquired a similar strut. She calls it the “Cuban walk.” She swings her hips back and forth, slowly, chin up, back arched, and looks like she’s making a statement. The girl I grew up with is now buried deep inside a 26-year-old who wears tight-fitting dresses and big hoop earrings. Or maybe she’s not buried at all. Maybe Cuba has tapped into a different part of Hannah that has been dormant this whole time.
One morning during my trip, we lay in her bed, the same way we did in high school, and talked about men, sex, and her experience in Cuba versus in the U.S. She told me how she'd grown into herself as a woman here — in a way she never had at home.
I think a big influence is the way Cubans approach sex. Kids in Cuba start learning about sex in preschool, and culturally, it’s viewed as an everyday part of life. Hannah says that in Cuba, when you’re hungry, you eat, when you’re thirsty, you drink water, when you’re horny, you have sex. Point blank.

Maybe Cuba has tapped into a different part of Hannah that has been dormant this whole time.

The Cuban government has progressive policies when it comes to the control women have over their bodies. Abortion is available and accessible here: There aren’t debates about it on television; it’s not on the political agenda; and there isn’t a stigma if you get one. It’s a decision. If you don’t want to have a child, you have an abortion. Hannah’s friends talk about it in a sterile way. It’s not emotional; it’s practical.
I think back to the Sex Ed classes we had in school, focused on abstinence and STDs. I remember the slut-shaming that would happen in the hallways, and the whispers, and the constant critiques of the feminine image.
Still, this sexual freedom in Cuba seems to favor heteronormative, cisgendered, feminine-presenting women. While Hannah is free to embrace her heterosexuality, queer women are forced to retreat from being themselves. It was only in 1979 that being homosexual became legal in the eyes of the Cuban government.
But for Hannah, living in Cuba means having nothing to hide. When she’s with one of the men she’s dating, I watch as she passionately kisses him in public, strokes his face, and calls him “mi vida” — "my life." I never saw her this way in the U.S. — this sexy self-assuredness. I can tell their chemistry is based on Hannah’s confidence in herself, her body, and who she is as a woman.
Photo: Courtesy of Megan Tan.
She doesn’t just use her sexuality and her femininity as a source of strength in her personal relationships; she’s learned to use this in her professional relationships as well. When we’re talking about networking with people in journalism and media, the way we prepare is different. Hannah’s priority is to look and feel amazing. To wear shirts and dresses that show off her curves and capture people’s attention. Her appearance is a reflection of the confidence she has in herself, while my priority has always been to be comfortable.
I've been taught not to embrace my femininity because it attracts negative attention. Hannah has tapped into a part of herself that I’m still navigating.
One night, as we’re preparing to go out, I reach in Hannah’s closet and pick out a black crop top. The Megan Tan in Maine would never wear this in public, but in Cuba I admire myself in the mirror, like someone I’ve never seen before.
There’s a phrase people say on the streets: “Estamos en Cuba.” It literally means, “We’re in Cuba.” When I leave Hannah’s house wearing a black crop top and a tight red skirt, I repeat it, “Estamos en Cuba,” as a way to give myself permission.
This feminine, openly sexual part of me may not follow me back to Maine, but in Cuba, alongside Hannah, at least I know it exists. In the same way best friends pull out the best parts of you, it’s apparent that foreign countries can do the same.

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