Frank Sinatra and Marilyn Monroe were two of the most famous and influential celebrities of their time, and it’s natural to assume that the two dated at some point.

In an autobiography titled Marilyn Monroe: The Private Life of a Public Icon, it was revealed that the two were in an “open romance,” where they decided to be romantically involved while seeing other people.

Author Charles Casillo says that their relationship would best be described today as a “friends with benefits” arrangement.

Despite the casual nature of their relationship, Sinatra had fallen in love with Monroe and treated her like he had never treated any other woman.

Sinatra was very protective of Monroe and asked her to marry him several times, to which she politely declined.

Monroe was once married to former baseball champion for the New York Yankees, Joe DiMaggio.

Their turbulent romance ultimately led to their divorce, but DiMaggio never stopped loving Monroe.

Until the day he died, he would send roses to his ex-wife’s grave every single week, as she had once requested.

He was so in love with Monroe that he was heartbroken to learn she had started up a new romance with the famous singer, Sinatra.

Feeling so betrayed by the crooner, DiMaggio banned Sinatra from attending Monroe’s funeral.

Sinatra’s lawyer refused to let the singer marry Monroe because of a tragic reason.

According to Casillo, “He actually went to his lawyer and said, ‘I think I am going to marry Marilyn,’ and his lawyer talked him out of it.

“The lawyer said, ‘Don’t marry her. She’s going to commit suicide, and if she kills herself during the time that she is Frank Sinatra’s wife, you will go down in history as the man responsible for Marilyn Monroe’s death.'”

Monroe died on August 5, 1962, at the age of 36. Sinatra was not allowed to attend Monroe’s funeral due to DiMaggio’s ban.

According to the New York Times, Sinatra did not attend the funeral, but sent a large bouquet of red roses with a card that read, “I will always love you.”

The cause of Monroe’s death was initially ruled as a probable suicide, but there have been several conspiracy theories over the years suggesting foul play.

In 2012, Los Angeles authorities reopened her case as a possible murder investigation, but after several months, they concluded that there was no new evidence to suggest that Monroe’s death was anything other than a suicide.

Monroe was buried in the Westwood Village Memorial Park Cemetery in Los Angeles, and her funeral was attended by many of her friends and fellow celebrities, including James Dean, Milton Berle, and Joe DiMaggio.

In a documentary titled Marilyn Monroe: Auction of a Lifetime, Monroe’s friend, Frieda Hull, revealed that DiMaggio’s flowers were always fresh and that he would send a new bouquet every week.

“Joe would always make sure that the flowers looked perfect,” Hull said. “They were always fresh, and he always had them delivered.”

Monroe’s grave has become a popular tourist attraction, with fans from all over the world visiting her final resting place to pay their respects.

Her legacy as an iconic Hollywood actress, model, and s^x symbol has continued to live on decades after her death, as has her complicated and often tragic personal life.