Gerber is quick to insist that even as a young teen, she was the driving force behind her career. And yet extreme youth had its drawbacks. “My dad would call me when I’d be in Paris and be like, ‘Do you want to come home?’ At the time I thought I was fine, but now I look back to 16-year-old Kaia and I’m like, ‘Come home!’ ” She pauses, the gravel crunching underneath our feet, the eager Milo straining at his leash. (“Yeah, bud, I know! It’s really exciting,” she murmurs.) “And I found myself in situations where I was, like, I actually don’t have the life experience that I need to handle this.” When I ask her what she means, she thinks for a moment. “It could be something as small as knowing how to take the bus from the flight to the terminal,” she finally says. “Or, I remember, when I started traveling alone, in Paris, my driver had to check me into my hotel room—I couldn’t even do it on my own.” When I wonder if she is also talking about matters of emotional maturity, she pauses again. “You know, I was doing fashion month, but I was so young I had kissed, like, only one person. I had never had a high school sweetheart or anything. And so I tended to date older people because those were the people I was around. And I got put in situations where one day I’d wake up and be like, How did I get here? I have no idea what I’m doing, and I need help. And being able to ask for that help was amazing. That’s what real growing up means, not being afraid to ask.”
Gerber is palpably guarded talking about all this and is hard-pressed to go into further specifics, and who could blame her? The last couple of years have seen the public interest in her and her family roar to a crescendo. In the fall of 2019, soon after she turned 18, it was reported that she was dating Pete Davidson, the then-26-year-old, heavily tattooed Saturday Night Live comedian and actor who has gained a reputation as a troubled lothario. If you’re inclined to believe the gossip sites, Davidson reportedly entered treatment around the time he and Gerber broke up. Presley, too, attracted increasing tabloid attention after he was arrested for a DUI at the end of 2018, and later got a face tattoo under his eye that read, misunderstood. “So many people have difficult teen years with their kids, and we thought we’d kind of skated through that period,” Crawford tells me. “And a little later, it hit us in ways we didn’t necessarily expect. But you just have to let your kids fly and be there to pick them up if they fall. My husband, who has a great perspective, always tells me, ‘Cindy, this too shall pass.’ ”