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Jenny Boylan Reflects on Coming Out as Transgender on The Oprah Show

Season 5 Episode 523
Aired on 04/23/2016 | CC tv-14
In 2000, Jenny Boylan, an English professor at Colby College in Maine, began her transition from male to female. Long before Caitlyn Jenner made headlines and the public developed a greater understanding of transgender issues, Jenny came to The Oprah Show to share her story.

On the plane ride to Chicago, she tells Oprah: Where Are They Now?>, she remembers feeling scared and finding solace in the phrase, "Trust your story. Don't be afraid." Today, she says, she looks back at the appearance as a pivotal moment in transgender politics.

Until that time, Jenny explains, "transgender people in the media were often treated like, you know, crazy people, and people would ridicule us and make fun of us. When I was on [The Oprah Show], I was treated with respect and with dignity, and I think it was a culture-changing moment."

Here, she reflects on the groundbreaking interview.

Tune in for Oprah: Where Are They Now? at 10/9c on Saturday, April 23.
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