What It’s Like to Date as a Transgender Teen

Transgender teen Jazz Jennings is a trailblazer in many ways — including dating, as the 15-year-old admitted to Oprah Winfrey in a new interview during which she shared that “boys aren’t really accepting” of her. 

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“I just go with the flow and see what happens,” the LGBT activist and reality star told Oprah Winfrey about how she’s approaching relationships during an OWN Where are They Now? special on Saturday. “If boys like me and I like them back then yeah, it’ll happen. But for the most part boys aren’t really accepting of me because I’m transgender. And therefore not many guys have crushes on me, at least at my school. They think that if they like me they’ll be called gay by their friends because they like another ‘boy,’” Jennings explained gesturing with air quotes. “They don’t see me as a girl.” 

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Jazz began living as a girl in Kindergarten. She shared a childhood photo on Instagram captioned, “#flashbackfriday to my glittery self.” (Photo: Instagram/Jazz Jennnings)

Ever since the Florida teen, born male, can remember, though, she has identified as female. At age 5 she was diagnosed with gender dysphoria and with the support of her parents, Greg and Jeannette, as well as older siblings sister Ari, and twin brothers Sander and Griffen, Jazz embraced her identity. 

Jazz and her family (Photo: OWN/YouTube)

But despite her self-assured persona in public — as a role model for LGBTQ youth with her TLC reality series I Am Jazz and honors, including The Trevor Project’s “Youth Innovator” award in December for the efforts of her TransKids Purple Rainbow foundation and Time magazine’s naming of her as one of the “25 Most Influential Teens of 2014” — the teenager’s private relationships have been a challenge. 

(Photo: Getty Images)

“I’ve had a pretty rocky relationship with boys in the past,” Jazz has admitted on TLC. “This one time this really cute boy liked me and then once he found out I was transgender he started calling me, ‘chick with a dick’ behind my back. Being trans has completely turned boys off liking me.” She says her female friends try to comfort her, “always telling me that I just have to be myself but it’s not that easy.” Boys, Jazz lamented, “always say hi to my friends, hug them, and not me and I’m just like right there and kind of being ignored and sometimes it hurts.” 

Jazz on OWN (Photo: OWN/YouTube)

Thankfully her self-esteem is constantly buoyed by her supportive parents and siblings. “I think I was born with a natural confidence inside and strength but my parents were able to help me realize that — not just my parents, my family,” Jazz told Oprah Winfrey. “They were able to help me realize that by giving me unconditional love and acceptance and just supporting me and I learned to love myself.”

(Photo above: Corbis Images; Top photo: Instagram/Jazz Jennings)

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