Chelsea Handler says one of the reasons she now prefers female ski instructors is a very personal one: after hiring a man to teach her in Whistler, she ended up sleeping with him and decided that, going forward, women were the safer bet.
During an appearance on Tana Mongeau’s podcast Brand Safe, the comedian said her passion for skiing took off when she stepped away from work for an extended period and decided to focus seriously on learning the sport.
“I’m glad all of my interests kind of relate to my career, and I was able to make a career out of my interests,” she said, reflecting on how her hobbies and work have intertwined over the years.
She went on to explain that what she first imagined as a relatively short career pause ended up becoming a much longer and more immersive experience.
“I thought I was going to take, like, two years off,” she explained. “I’m going to take two years off. I want to learn how to ski. That would be my most fulfilling thing.”
Handler said she headed to Whistler in Canada, where she now spends time in the winter, and dedicated herself fully to improving her skiing. She recalled spending nearly two months on the slopes without a break, staying at the Four Seasons throughout the winter and employing a private guide to help her progress.
“I spent 55 days skiing every single day,” she said, explaining that she checked into the Four Seasons and based herself there for the entire winter season while hiring a private guide to teach her.
That period on the mountain ended up taking a more personal turn than she had expected.
Handler said she eventually became involved with the male instructor she had hired, and that experience is what led her to rethink who she books for future ski sessions.
“I paid some man who I ended up sleeping with,” Handler told Mongeau. “So then I had to start hiring a woman. I had to do that too.”
Looking back on why that keeps happening, Handler said the attraction seems connected to the trust she places in people who are responsible for her wellbeing.
“It’s when someone’s in charge of your body in any sort of way, like in charge of keeping me safe, I’m attracted to them,” she explained.
Handler has often spoken about how much she enjoys skiing, frequently posting from Whistler and organizing women-only ski trips for fans. In recent interviews, she has also continued to discuss dating, aging and the ways she has built a life around travel, skiing and comedy.