Would-be assassin John W. Hinckley Jr. invited two dates to the same party. He had a relationship with a woman deemed “floridly psychotic.” He raved to treatment providers about movies he hadn’t seen. And he looked up photographs of his female dentist on the Internet, then feigned a toothache to see her again.

Are those the harmless misjudgments of an arthritic, gray-haired 56-year-old who has spent three decades in a psychiatric hospital? Or are they warning signs that the presidential assailant may still be dangerous?

Those are the questions a federal judge must answer as he weighs a request by Hinckley’s doctors and therapists to expand his liberty and give them the authority to place him in Williamsburg, his mother’s home town.

In the first five days of court hearings that will help determine Hinckley’s future, testimony and records provided a rare glimpse into the life and mind of a loner who, driven by a delusional obsession with a movie actress, nearly killed President Ronald Reagan and wounded three other men in 1981.

U.S. District Judge Paul L. Friedman heard from Hinckley’s relatives, doctors and therapists, who said he was ready to more fully reenter society as part of his continued therapy. Prosecutors disagreed, and they may begin making their case as soon as this week. The proceedings should wrap up next month, and Friedman could rule anytime after that.

John Hinckley Jr. arrives at U.S. District Court on Tuesday, Nov. 18, 2003, in Washington. (EVAN VUCCI, AP)

Hinckley’s depression and unspecified psychotic disorder are in remission and his narcissistic personality disorder has receded, according to court testimony. Doctors and therapists have testified about more than a dozen 10-day visits Hinckley has made to his mother’s home in a luxury golf community; they have delved into his relationships with women; and they have probed his honesty and his maturity. The portrait that has emerged is not flattering.

Still, his lawyers and doctors say that while Hinckley has occasionally exhibited what his doctors call “poor judgment,” he remains a “low risk” for future violence, the standard upon which Friedman will rule.

“Although flawed,” says his attorney, Barry Wm. Levine, “he is surely not a danger to himself or others.”

Federal prosecutors say that Hinckley is too deceptive and lazy to be trusted and that the hospital is “gambling” in seeking more freedom for a gunman who nearly killed the president and permanently disabled a White House press secretary.

“Mr. Hinckley has not been a good risk in the past and, therefore, is not going to be a good risk in the future,” Assistant U.S. Attorney Sarah Chasson said.

Hinckley, who has been held at St. Elizabeths Hospital in Southeast Washington since being found not guilty by reason of insanity in 1982, has said nothing during the hearings. Wearing a sports coat and tie, he has slumped in his seat at the defense table, chewed his bottom lip, fiddled with plastic cups, yawned and whispered to his lawyers.

In Williamsburg, which he has visited regularly since Friedman expanded such privileges in late 2005, Hinckley’s days are strictly regimented, according to hospital records. On most days, he awakens early and does chores. If his arthritis isn’t acting up, he goes on a two-hour walk. He then sees movies or shops at outlet malls or stores selling music, books or pet supplies.

Twice a week, he volunteers in a psychiatric hospital’s library. And once a week, his mother escorts him to appointments with a therapist and a psychiatrist.

He plays his guitar and listens to Bob Dylan or the Beatles. He paints landscapes, houses and cats — artwork that adorns the walls of his room at his mother’s home. On some trips home, he brings along one of the feral cats he tends at St. Elizabeths. Having obtained a driver’s license in January, he sometimes drives to his various activities. More often, according to prosecutors, his mother or one of his siblings drives.

By all accounts, Hinckley is close to his mother and relies on her extensively during his visits to Williamsburg. Much like the mother of a busy teenager, she lines up his appointments and shuttles him to and from activities. However, Jo Ann Hinckley just turned 86, and the hearings raised questions about the hospital’s Williamsburg plan if she “becomes unavailable.”

There do not seem to be many alternatives. The hospital has invested much time in its plan, and Hinckley has formed bonds with his therapist and psychiatrist in Williamsburg. (Both are paid for by the Hinckley family, whose finances are “dwindling,” according to his attorneys.) Hinckley’s father died in 2008. The District, where he has spent the last 30 years, is off limits, other than the hospital. And Dallas, where Hinckley’s siblings live, is also problematic; his sister, for example, lives just 10 minutes from former president George W. Bush.

Though his lawyers and doctors say Hinckley could make Williamsburg a permanent home, prosecutors say Hinckley has not tried hard enough to integrate into the community.

During the past six years, the introverted Hinckley has yet to make a single friend in Williamsburg. Prosecutors have criticized him for rarely venturing from his comfort zone, choosing to go to the same stores and restaurants and often refusing to try activities suggested by his therapist.

When Hinckley has ventured beyond his itinerary, he has gotten into trouble.

In July, his mother dropped him off at the movies. Instead of seeing “Captain America,” Hinckley headed to a nearby bookstore, according to a Secret Service agent’s report. Hinckley was spotted browsing shelves that contained books about Reagan, including one about his attempted assassination. (The only book he was seen reading, however, was about British rock music and culture.)

When he returned to St. Elizabeths, he raved about the film to his treatment providers.

In September, he slipped away from the theater again to browse books and then gave high praise to “Rise of the Planet of the Apes,” which he also had not seen.

Hinckley’s relationships with women also have been under the microscope. Referred to in court by their initials to protect their privacy, the women appear to be current or former mental patients at St. Elizabeths.

First, doctors dissected Hinckley’s relationship with “Miss G,” who dated Hinckley even though she had a live-in boyfriend at the time. They broke up in 2008, and Miss G moved to France with her boyfriend. She has since returned without the boyfriend, leading Hinckley to tell a psychiatrist that she “was back in the picture.”

He invited Miss G and another date to the same hospital Christmas party in 2008, a decision a St. Elizabeths psychologist called “poor judgment” because he did not respect the hospital’s rules and seek approval to invite Miss G to the party.

Then there is “Miss C.B.,” a woman with her own serious psychological issues. In February, according to a St. Elizabeths report, Miss C.B. entered the hospital’s grounds manic and delusional, “ loudly shouting religious words and Mr. Hinckley’s full name.”

A month or so later, Hinckley asked C.B. to marry him, giving her a ring he told a psychologist resembled the one Prince William gave Kate Middleton. “He was bubbling with excitement” after the engagement, testified Katherine Murphy, a St. Elizabeths psychologist.

Still, Hinckley never told his siblings about his wedding plans — prompting questions from prosecutors about what else he might be hiding. Hinckley eventually called off the engagement.

There was also a “Miss X.” Hinckley pursued a relationship with her, prosecutors said, because she would ask him for “affectionate gestures, caresses, hugs and kisses.” She was described by prosecutors as “floridly psychotic.”

A psychiatrist testified the relationship did not mean Hinckley was dangerous but rather that he showed “poor judgment in who he chooses as a female friend.”