Caitlyn Jenner Recalls 'Dark Days' Surrounding First Attempt at Transitioning in the 1980s

Caitlyn Jenner is opening up about the challenges and setbacks she faced during her first attempt at transitioning, back in the 1980s.

The 66-year-old reality star and Olympic gold medalist opened up in a revealing video interview at this year's AOL Makers Conference in Rancho Palos Verdes, California on Tuesday.


"Those were real dark days for me," Caitlyn said of her life in 1986. While still living as Bruce Jenner and having gone through two divorces -- first from Chrystie Scott in 1981, after nine years of marriage, and then from Linda Thompson, after four years -- the celebrated athlete felt like life was at a "crossroads."

"I [had] a house in Malibu, I basically stayed there for six years," Caitlyn recalled, "and I really started struggling with my identity, [asking], 'Who am I?'"

"I tried to start doing things to make me feel better about myself," she shared. "I started on hormones. But yeah, I was a good 36B, and I'm going, 'Oh, God. OK.' I loved them, you know, I thought: 'This is fabulous.'"


"My mission at that point was to transition before I was 40," Caitlyn explained. "I got to 39, and I just couldn't go any farther."

"Three or four months later, I met Kris [Jenner]. We hit it off from day one," said Caitlyn, who started dating Kris in late 1990. The couple tied the knot five months later in April 1991. "I was very honest with her [from the beginning]. I had to be, I was a 36B. But [I told her], 'I'm a good person. I'm fun.' We had a great time."