Three stints in jail. Four trips to rehab-and counting. At 24, can the deeply troubled actress ever get the help she needs?

By Michelle Tauber and Liz McNeil
Updated October 11, 2010 12:00 PM

To be friends with Lindsay Lohan is to become entangled in a twisted version of the classic children’s rhyme: Round and round and round she goes-and where she stops, nobody knows. But many who know her best tell depressingly similar tales of what it takes to keep up with the deeply troubled star: There are the desperate 3 a.m. texts to keep her company while she tries to sleep, because she can’t stand to be alone, ever. There are the constant pleas to go out partying in the wee hours. And there is the sense that as Lindsay’s life spins increasingly out of control, so does her grip on reality. On Sept. 11, just 18 days after being released from court-ordered rehab, the actress went to a party at the Manhattan club Boom Boom Room. But when a confidante asked where she was, “she told me she was home,” says the friend, who’s known Lindsay for several years. “I said, ‘I heard you went out.’ She was like, ‘Don’t be ridiculous. I wouldn’t go out. They’re all liars.’ She thinks that if she tells herself [something] long enough, it will actually be true.” Confront Lindsay and risk being frozen out: “When I said, as did many people, ‘We will not stand idly by and watch you totally destroy yourself,’ is when she stopped being honest with me,” says the friend. But walking away from her isn’t ever simple. “Even when you’re like, ‘I need to distance myself,’ she brings you back in. At the end of the day, she is a very loving, sweet girl who’s just so mixed up. There’s no way out for her.”

By her own admission, Lindsay is a 24-year-old addict, trapped on an endless carousel of relapse and rehab, courthouse and jail. Each time she stumbles, she swears that this time things will turn out differently. But many of those who have tried to help Lindsay are losing hope. Just four days after her Aug. 24 release from substance abuse treatment at UCLA, she was back on the nightlife scene at L.A.’s Chateau Marmont. Within the month she tested dirty for drug use. “There is no awareness level,” says a business associate. “She’s never thought she needed help.” But Lindsay’s brother Michael Jr., 22, disputes this, telling PEOPLE in an exclusive statement, “She’s well aware that she’s at a crossroads in life and is fully committed to ensuring a healthier future.” Ordered back to jail by L.A. superior court judge Elden Fox until her next court hearing on Oct. 22, the actress barely had time to pose for her fourth mug shot before an appeal got her released on $300,000 bail. After reportedly soliciting money from paparazzi to snap photos of her wearing an alcohol-monitoring ankle bracelet (her third), Lindsay joined mom Dina, 48, and sister Ali, 16, in a visit to an L.A. homeless shelter on Sept. 26. “It’s so important to give back,” she tweeted. “I feel blessed.”

Most people didn’t quite see it that way. Multiple sources say the onetime Disney darling is planning to check into rehab for the fifth time. “Lindsay knows she needs to get above all of her issues, including her addictions and her deep-rooted issues with her father,” says a member of her inner circle. But many others who know her worry that Lindsay seems incapable of digging herself out from under the mountain of denial, addiction, excuses, insecurity and entitlement that has buried her. “She still blames the world, her parents, the courts, her friends, everyone. For everything,” says a friend. “She will have a moment of clarity and say things like, ‘My life is a mess. What have I done?’ But those moments are short and they don’t stick. She drifts off into crazy land, thinking she’s done nothing wrong and everyone is out to get her.” Her self-destructive behavior has friends fearing for her life. If she continues down this path, says a former colleague bluntly, “I don’t think she’ll survive.”

On Sept. 17, just after finding out she had failed a drug test and tweeting, “I am a work in progress, just as anyone else,” the actress hit L.A.’s Magnolia, where she snuck sips from friends’ vodka cocktails. On Sept. 27 grainy photos surfaced in the British tabloid News of the World allegedly showing the actress preparing to inject a syringe at a 2007 party. “This was a [vitamin] B12 syringe, not a heroin needle,” says the member of her inner circle. “Lindsay has never experimented with heroin.”

The young woman who can’t bear to be by herself often appears utterly alone. A cluster of friends and family (see box) has stood by her. But even those closest to her acknowledge she hasn’t always attracted the right people. “In the past, her vision had been blurred. People she was surrounded by (enablers, leaches, whatever you like to call it) made things very difficult,” says Michael Jr. Adds one longtime friend: “To be friends with Lindsay takes a lot of drama, so it’s all these wannabe people or rich kids who have disposable income and think it’s cool to hang out with a celeb.” Lindsay’s staunchest defender, mom Dina, maintains that her oldest daughter’s struggles are “blown out of proportion,” as she told Matt Lauer on Aug. 13. “She’s in complete denial,” says another old friend of Lindsay’s. The inner-circle source maintains that “Dina had certain legal obligations to protect Lindsay, and so she seemed to be in denial in that interview, but it is not the case. The person who is challenging her the most is Dina.” Meanwhile, Lindsay’s father, Michael, 50, against whom Dina has a restraining order, acknowledges Lindsay’s issues but constantly courts publicity. “Lindsay can’t stand Michael,” says the pal.

While former wild-child friends like Nicole Richie and Britney Spears have turned their lives around with parental support, Lindsay shows no sign of changing her ways. Her career has suffered acutely as a result, with few producers willing to subject their projects to her erratic life. Her only scheduled upcoming film, a biopic of porn star Linda Lovelace, has been postponed again. As a result, her income is now largely dependent on a handful of endorsements and promotional appearances. Yet when she does act, sources say she still shows signs of her early talent. “When the cameras are rolling, she has this odd awareness,” says producer Rick Schwartz, who worked with her on this fall’s Machete and 2009’s Labor Pains. “Having grown up on sets, it’s very instinctive to her.”

For now Lindsay’s court-ordered restrictions-among others, she is barred from entering any establishment where alcohol is the chief item of sale-are meant to keep her on a short leash. If she can stay on it. On Oct. 22 she could be ordered to do more rehab or go back to jail. But will she finally commit to hopping off the merry-go-round once and for all? “Deep down, I think she knows she’s in crisis,” says the former colleague. Adds one of her close friends: “This might be it. But still, the attitude of some of her friends is, ‘Oh no, not again.’ It never ends with her.”