Washington (CNN) -- John Hinckley Jr.'s relationships with women and his difficulties becoming part of a community away from a government mental hospital were spotlighted Thursday during a hearing to discuss whether the man who tried to kill President Ronald Reagan will eventually be allowed to live as an outpatient.





An official at St. Elizabeths Hospital, where Hinckley, 56, has lived for decades after being found not guilty by reason of insanity, said Hinckley had been engaged to a former patient he met at the hospital. She was identified only as "Miss CB," but the engagement recently ended.





Dr. Tyler Jones, the facility's director of psychiatry, said Hinckley had given the woman "multiple rings."





Jones said Hinckley had told him he'd explained to CB he planned to spend more time visiting his mother's home in Virginia and would be spending less time with her. As a result of that conversation, "she's withdrawn the physical affection that they shared," Jones said.





Federal prosecutor Colleen Kennedy also questioned Jones about Hinckley's past relationship with a patient identified as "Miss X." Kennedy said Hinckley had difficulty communicating with the woman because she was so psychotic, but he pursued the relationship because she was physically affectionate.





Jones described Hinckley's actions as "poor judgment" motivated by his "desire for affection."





According to Jones, another doctor told Hinckley the relationship was ill-advised and eventually Hinckley ended it.





Hinckley has been spending 10 days a month visiting his mother in Williamsburg, Virginia, where he works part time as a volunteer in the library at Eastern State Hospital, a mental health facility. Doctors have been encouraging him to make friends in Williamsburg and build a new life.





Jones said Hinckley has had some difficulties. In one instance, he followed a suggestion to go to a singles group, but that did not turn out well. "He was asked to leave," said Jones, because one participant was very uncomfortable with his presence.





Since Hinckley likes music and plays the guitar, one of his doctors suggested he go play for hospice patients. But Jones said Hinckley never went because the hospice was worried there might be negative publicity if the presidential assailant played there.





Another possible avenue for meeting people also has not panned out. Jones said Hinckley, when in Williamsburg, had not been interested in going to a gym or participating in certain sports like golf or tennis, either because of arthritis or because he finds the activities unappealing.





The doctor said Hinckley's "treatment team" wants him to spend more time in Williamsburg and thinks he'll be able to fit into the community much better.





A clinical psychologist from St. Elizabeths who has met with Hinckley five times conceded he's been unable to form relationships in that small city so far, aside from those with family members. "He had not made a friend in Wiliamsburg," said Katherine Murphy.





She stressed that Hinckley is an introvert and not the type to quickly make a lot of friends."He's just not someone who goes and out and meets people or is a social butterfly."





But Murphy said Hinckley seems to have coped adequately when rejected in social situations and is "not showing signs of isolation." Murphy was involved in a psychological risk assessment of Hinckley. Both she and Dr. Jones said Hinckley represents a low risk of engaging in violence if granted permission to spend more time away from his mental hospital.





A multiple-day hearing began Wednesday to discuss St. Elizabeths' recommendation that Hinckley be granted a series of eight longer visits ranging from 17 to 24 days. That plan also proposes that eventually the hospital would have the authority to let him live as a full-time outpatient.





Prosecutors oppose the plan, saying they are concerned Hinckley is still potentially a danger. In opening arguments Tuesday, prosecutor Sarah Chasson said the court should not allow Hinckley to be released "to protect public safety."





Chasson said Secret Service agents will testify they kept an eye on Hinckley in Williamsburg during the short periods of time earlier this year when he was allowed free time on his own. According
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