The bounds of Frank Sinatra and Marilyn Monroe’s relationship are not entirely clear. While some claim the pair came close to marriage, others report that their relationship was only a friendship. Regardless, the two were close for a period of time. After her death, Sinatra reportedly became convinced that she was murdered, something that haunted him for years to come.

Frank Sinatra and Marilyn Monroe had an undefined relationship

According to the book Marilyn Monroe: The Private Life of a Public Icon, Sinatra and Monroe were in an open relationship. Despite this, author Charles Casillo claims that Sinatra had fallen in love with her.

“Like many men, Frank Sinatra fell under her spell. He treated her like he had never treated any other woman,” Us Weekly reports that Casillo said. “He was very protective of her.”

Casillo also said that Sinatra intended to propose to Monroe, plans that were ultimately thwarted by his lawyer. On the contrary, Sinatra’s close friend and former road manager Tony Oppedisano says the two were simply friends.

“Frank felt she was too troubled, too fragile, for him to sleep with and then walk away,” Oppedisano said, per People.

He believes someone killed her

In 1962, a staff member found Monroe dead in her home. Authorities concluded that her likely cause of death was suicide. As with many celebrity deaths, rumors and conspiracy theories abounded. With Monroe, this was particularly true because of her connections to the Kennedy family. In particular, Monroe’s alleged relationship with John F. Kennedy draws suspicion. Oppedisano wrote about the nature of their relationship, noting he believes Monroe had feelings for Kennedy, but he does not think she loved him.

Shortly before her death, Oppedisano says Monroe was planning to make a press statement, sharing that she and ex-husband Joe DiMaggio were getting back together. Oppedisano believes that she was also going to reveal details about her relationship with Kennedy during the conference.

“Frank believed if the press conference hadn’t been announced, she would have lived a lot longer,” he said.

Conspiracy theorists believe the mafia or someone close to the Kennedy family murdered Monroe. Oppedisano won’t speculate on either, but he does know how Sinatra felt about it.

“Frank believed she was murdered,” he wrote, “and he never got over it.”

Frank Sinatra could not go to Marilyn Monroe’s funeral

Though he held deep feelings for her, Monroe’s loved ones did not allow him to attend her funeral. DiMaggio believed the singer was in a romantic relationship with Monroe. Though he never had proof that Sinatra and Monroe were romantic partners, he firmly believed it. This was enough to keep the singer far away from the funeral.

How to get help: In the U.S. and Canada, text the Crisis Text Line at 741741 to reach a crisis counselor for support.

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