Oprah Winfrey Asks Lindsay Lohan: Do You Think You Are Addicted to Chaos?

First Look: Lindsay Lohan on Oprah's Next Chapter

Oprah and actress Lindsay Lohan come together for an exclusive, highly anticipated conversation. Tune in Sunday, August 18, at 9/8c.

Oprah Winfrey wasn't going to let Lindsay Lohan get off easy! Judging from a preview clip of the troubled star's sit-down conversation with Oprah for an upcoming Oprah's Next Chapter segment, the 27-year-old actress gets grilled by the TV host, who asks her a range of honest, if not difficult, questions.

In the clip, the OWN media mogul asks questions like "Do you think you are addicted to chaos?" and "What's going to be different this time?" to a wide-eyed and somewhat bewildered Lohan, who was released from rehab on July 30 after completing a court-mandated 90-day stint. (In total, The Canyons' star has spent 293 days in rehab since her first stint in 2007.)

Lindsay Lohan on Oprah
Lindsay Lohan answers Oprah's questions for an upcoming Oprah's Next Chapter episode. Stephen Lovekin/Getty Images for Mercedes-Benz Fashion Week

She also asks Lohan about her previous legal problems, asking the former Disney star if her first DUI was a wake-up call. "What does it feel like to be — both an adjective and a verb — for a child actor gone wrong?" she asks the Mean Girls alum during the clip. 

Indeed, Oprah said of the Aug. 3 sit-down with the actress that she is cautiously optimistic about Lohan's recovery. 

"All I can say about it is this: I believe that she believes that she is ready to move forward in her life," Winfrey told Al Roker on the TODAY Show on Aug. 5. "And we'll see."

The 59-year-old added, "I'm anxious to see whether or not this young woman, who is a really, really fine actress, will be able to allow us into her life and let us see the trajectory of trying to put the pieces back together."

See Lohan on Oprah's Next Chapter on Sunday, Aug. 18 at 9pm.

Watch the preview clip now!

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