In the 1950s and 60s, Frank Sinatra and Marilyn Monroe were two of the hottest celebrities in Hollywood.

The relationship between the two has never been clear, but they did feel deeply for each other.

Charles Casillo wrote that Sinatra and Monroe were in an open relationship and that he once wanted to marry her.

Tony Oppedisano wrote that the two were just friends and that Sintra felt Monroe was too troubled and fragile for a casual relationship.

Monroe’s life in the year before her death was chaotic, and she suffered from substance abuse and declining mental health.

When she was found dead in August 1962, authorities concluded that her death was a suicide, but there were many contrary conspiracy theories.

Oppedisano wrote that shortly before Monroe’s death, she planned a press conference to announce her reunion with DiMaggio.

He also believed she might have revealed her relationship with John F.Kennedy, and Sinatra believed this was why she was murdered.

Because of her relationship with Sinatra, DiMaggio barred him from attending Monroe’s funeral and saying goodbye to her.