Jenny Boylan used to be Jim Boylan.
PAGE 4
In April 2005, Oprah interviewed Jenny, a woman who'd previously been known as Jim, a married male college professor. "Jim told his wife, Deedie, that he had to have a sex change or he would die," Oprah says. "And get this—they stayed married."

After the interview, Oprah received a letter from Jenny and Deedie's oldest son, 13-year-old Zach. "Sometimes it's hard to have a family that's different," he wrote. "But most of the time I feel like the luckiest kid on earth."

Zach is 15 now and says he can hardly remember the time before Jenny's transition. "I remember Maddy before she was a woman, but I don't remember that time between Step 1 and Step 2," he says. Zach says he calls Jenny "Maddy" because it's a combination of mommy and daddy.

When Zach's friends ask who Maddy is, Zach says he's honest. "I say, 'My mom who used to be my dad.'"  
FROM: Oprah's Most Memorable Guests
Published on April 21, 2009

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