"My impression of Lindsay is that she's a fragile lost child – a sleeping beauty with her head in the sand. I found her not fully forewarned of the consequence of her actions," Stuart V. Goldberg, who was contacted by Lohan after her attorney resigned, tells PEOPLE.
"I'm concerned that she's not disciplined or tethered enough to the reality of adult consequences," he says. "She doesn't seem to have the awareness of what's going to befall her."
Goldberg, a criminal defense attorney based in Chicago, says he met with Lohan, her mom Dina and younger sister Ali at the actress's West Hollywood apartment and outlined his requirements for representing her – "100 percent loyalty and zero tolerance for dishonesty"– but "they didn't seem to understand the urgency and gravity of the situation."
He ultimately declined to take on the case.
During their six-hour long "heart to heart conversation," Lohan, 24, took notes like she did in court, writing in the triangular corner of a piece of paper, while Ali asked him "astute" questions.
At one point in their meeting, Goldberg, worried that Lohan "was in a dangerous state," asked if she might hurt herself.
"She started sobbing quietly. She was genuinely in pain," says Goldberg.
And though he advised Lohan to move out of Los Angeles, which he described as a "toxic environment for her," the actress didn't seem open to the idea.
"She was like Teflon to that comment," he says. "It just slid right off her. She seemed to have some inner deep sadness that that was her fate."
"My real worry for her is not just the jail time," adds Goldberg, "but my fear is that she's overly susceptible to a probation system that's set up for her to fail."
Reporting by KEN LEE