After high school, Casares went to the University of Miami for a year, where she fell in love with a fellow student, took off with him on his motorcycle and moved to North Carolina. "It was a very dysfunctional relationship, to say the least," says Casares. She laughs at her stupid, youthful self. "I really wanted to be a free spirit. But I don't think that anybody interpreted it then as free spirit. There was a lot of experimenting with drugs, drinking, sex. I don't think my parents slept."
Casares, who, like Madonna, was once a fanatical runner and now does yoga, is in great shape, though over four lunches I never saw her actually consume anything but coffee. "I never eat," she says. One afternoon in February, over lunch -- well, my lunch -- at Jerry's in SoHo, I mentioned the time we talked about rehab at Madonna's house the day we met. "Well, they were all getting stoned," she said, laughing. "By nature, I'm very addictive, compulsive, obsessive. In the long run, it paid off, because I'm that way with my work now. I'm that way with everything: drugs, alcohol, food, sex, working out, whatever makes you feel good. And you know it doesn't feel good anymore. I led that overindulgent lifestyle in the eighties that everyone did. I'm an excitement junkie. The adrenaline, I need it 24-7. I don't need it as much anymore, but back then that's all I lived for. We should have had extreme sports back then because I would definitely have participated -- it would have been healthier."
For seven years after high school, Casares drifted around, attending "a lot of colleges" and working at menial jobs (tanning-salon receptionist, valet parker) before finally getting a degree in English and public relations from the University of Maryland. In 1991, she moved to Los Angeles and started working as a model booker for Wilhelmina Men -- a job she hated and "wasn't very good at." She started dating Sandra Bernhard (whom she'd met backstage at Bernhard's one-woman show in Miami the year before). Bernhard took Casares to Madonna's birthday party, where Madonna was "very nice to me. She was polite and interested in what I had to say."
Their relationship developed in Miami, "when I shot the Sex book with her," says Casares. "We realized we had a lot in common and liked to go running, and that's where we kind of bonded." Queer-gossip legend has it that Madonna stole Casares from Bernhard, and that Bernhard felt betrayed. Whatever happened, Casares and Madonna remain estranged from Bernhard. (When I contacted Bernhard's publicist to ask for an interview, she snapped, "Why would Sandra want to talk about her? What good could possibly come from it?")
"We're cordial," says Casares. "There's no animosity." But then she can't resist: "Obviously, I'm not the one with the animosity. Did you see her show? It was brilliant. I laughed my ass off, but it was based on putting a lot of people down and joking about their misery. It provoked a lot of anxiety for me." Then, schizo-like, back to the nicer version: "She's one of the funniest, most brilliant people I've ever met. I have nothing bad to say about her." Finally, she arrives at this: "I've always had a theory that you meet people to meet other people. I met Sandra because I was supposed to meet M. It's very obvious."
Liz Rosenberg, who has worked with Madonna since the beginning of her career in the early eighties, adores Casares. "She's been a wonderful friend to Madonna," she says, "in ways that people will never know. She takes a lot of shit for being Madonna's friend. And I find her very brave for that. People think, 'Oh, she's just using Madonna. She's the PPF -- Paid Professional Friend.' But she's as great for Madonna as Madonna is for her. In a very cute way, Ingrid just refuses to take Madonna seriously. Like, they're in the car and Madonna will be screaming, 'Ingrid! Why did you turn there?!' And Ingrid will just say, 'Shut up, Madonna.' And laugh. People need to tell Madonna to shut up. Madonna hates getting her ass kissed, and Ingrid is the last person who would do that."
Becky Fajardo says the reverse seems to be true, too. "Madonna seems to be the only one who can control Ingrid. She is the only person who I have ever seen singlehandedly put Ingrid in her place, because it's not easy. Don't get me wrong: Ingrid is the sweetest, most harmless person in the world. It's just that she kind of imposes almost a fear in people, which makes her seem untouchable when she's really not. She's really just this little girl."
When Casares showed up at Jerry's that day in February, one of the first things out of her mouth was "Madonna would be happy to talk to you for this piece." A couple of months later, when I decided to cash in my chip, she'd changed her tune. "She doesn't want to do it," Casares said. "You know how Madonna is." (Well, no, actually I don't.) Eventually, I got a canned, boring quote through Rosenberg's office. I pushed Rosenberg again to get Madonna on the phone, and got another, slightly longer quote dictated through Rosenberg's assistant: "I don't really like talking about friendships because it trivializes it. Ingrid looks at life with innocent eyes. She is like Puck in A Midsummer Night's Dream. She is always up, smiling, and happy. She's a joy to be with and she's up for anything. She has a great sense of adventure." One can either look at this cynically -- that when push comes to shove, Madonna doesn't want to talk about anyone but herself -- or kindly: that her friendship with Casares might actually be one of the most important of her life, and she doesn't want to turn it into magazine fodder. Either way, what she finally did have to say is echoed by Casares's other friends.
"There's something very calming about Ingrid's childlike approach," says k. d. lang. "She's trustworthy on a very deep level to people who have lost trust, people in the public eye. And there's consistency in Ingrid that a lot of people don't get. She's always, always behind Madonna, no matter what's going on. She's always there for me. She's really solid on a very personal level, which is different than what one would perceive of her in the press."
"That she's a star fucker?" I say.
"She is a star fucker!" lang shoots back. "And one of the things I love most about Ingrid is that she has definitely said to me, 'I'm a star fucker.' To me, that's more respectful than someone who is and denies it. She knows she's a socialite."
On a drenching April afternoon -- the day Casares is turned down by the State Liquor Authority -- she leaves her lawyer's office on East 54th Street and ducks into a Town Car, clutching a sleek, black leather briefcase to her chest.
"In Miami we welcome everyone from New York with open arms. I come up here," she says with disgust, "and I feel like I was treated like shit. In Miami, I can make anything happen. It's easy. Two seconds, it's done. I've always considered myself kind of a New York girl. My friends, connections, business associates are all here, so I always found myself very accepted in that way, but when it came time to own a business here, I was vetoed so bad. I wanted to be able to pick up the phone and call the mayor like I do in Miami, and I can't do that here."
As the car inches through the rain, Casares grows quiet, sinks further down into the black leather seat and stares out the darkened window. After a minute or two, she laughs her funny, nervous, staccato giggle. "You have to keep up with the Joneses, and you have to have the right people and the right elements and all that right shit, and it's exhausting. Next time," she says with a smirk, "I'm going to open a nightclub in Cincinnati, by the airport. Someplace where I don't have to be fabulous."