By Shana Naomi Krochmal
Twenty years after her most serious relationship ended, she has tried at big love a few more times: Friendships became more only to fizzle out again, and a family of exes and comrades who take care of each other make it a little too easy to stay single. “I like to think that I’m fearless and go through life boldly,” she says. “This is a cherished little window of time you have, so you’ve got to grab it and live it large. Except, in this area of life, I’ve been scared and putting it off and making all kinds of excuses. I know I’ll be in love again. But I’ve been really reluctant.”
But then her mother died at 82, after they had found a fragile, tender friendship. Nyad was still in unbelievable shape, but found no solace in physical exertion. At her most serene, she’s a worrier, a second-guesser, and as the big birthday neared, she became overwhelmed with regret.
“I would do a 100-mile bike ride in a day, out to Santa Barbara or Palm Springs. And the whole time, it would be like, Why? Why didn’t I throw him off me? I was bigger and stronger when I was 14 than I am now. Why didn’t I walk his ass into the principal’s office? Why? Why didn’t I say this yesterday to the guy at the shop? Just second-guessing everything. It was ruthless. It’s good to examine a life. You need to move forward and you need to learn. I’ve done plenty of that—this was just a constantly revolving regret and self-bashing: I really don’t deserve this. I’m really not that good. Somebody’s going to find out I’m a fraud. Most people say that; almost all people are thinking it. And when I turned 60, I thought, Am I going to do this another 22, 25, 30 years, and that’s going to be it? I’m sick of it. I’m going to stop it.”
So she came up with the biggest, most outrageous-sounding idea, a desperate lifeline that would require every ounce of her attention. She set her sights as high as she could imagine: She would go after the great white whale, the Cuba-to-Florida swim that had eluded her three decades before. She calls it, a bit cultishly, her “Xtreme Dream,” but it had an extreme impact on her outlook.
“We’re a new generation of 60,” she says. “I want to feel alive and alert and awake and empowered. I’m in this rapture now, but it’s taken time to get here. I have friends who say, ‘Diana, you were always like this.’ So I guess I see it differently than how I’ve been behaving it.”
She went back to fundraising, finding sponsors and raising money to cover the cost of some 35 crew members, support staff who would help plan the perfect moment to start, who would help chart a course and then follow her lead, who would kayak alongside her with shark-deterrent electrical cords trailing down into the depths: medical advisers, nutritionists, oceanographers, meteorologists, and more.
All of them -- not to mention a significant media presence and millions of followers on her blog and on Twitter, hitting refresh over and over for an update -- were there last summer. They all watched as her first venture was aborted (allergic reaction to pain medication for an injured shoulder) and her second attempt ended abruptly (two painful, potentially lethal attacks by box jellyfish, among the most dangerous predators in the ocean), both far from the final destination in Florida.
“It’s not easy for me to let go of this dream, and I’m in distress about it,” she told CNN, which shadowed her for much of 2011 for a documentary.
This time, she only wallowed in regret for a few days. She decided to try again. “I’m always focused on it,” she says. “Go to sleep with it. Wake up with it. It’s a really tough stretch. It’s not just 100 miles -- it’s a tough 100 miles. If we can just make it through the jellyfish and I’m not attacked by a shark or something... What I worry about is getting across. I don’t worry about how I’m going to feel at the end.”
Through this long winter and spring, she’s built her way back up, swimming six hours a day in a lap lane that the Rose Bowl Aquatic Center in Pasadena keeps reserved for her, then ocean-training for eight or 10 hours at a go. When we speak in May, she’s essentially commuting between L.A. and Mexico, where she does 12-, 14-, and 16-hour swims, alternating with days off, then heads home to recover and put back on the weight she’s lost. (In the three days or so it takes to swim from Cuba to Florida, she’ll lose somewhere between 15 and 30 pounds.)