Marilyn Monroe Was Linked to Lots of Men, but These Are the Lucky Few Who Won Her Heart

After her divorce from Arthur Miller, Marilyn found solace in the arms of her longtime friend Frank Sinatra. The singer, who was going through a tough time with his estranged wife, Ava Gardner, let Marilyn stay at his home until she got settled again in LA, and a romance blossomed. The two dated for several months before going their separate ways, and in early 1962, Marilyn purchased her home in Brentwood, CA.

According to the 2015 biography Sinatra: The Chairman, Frank wanted to marry the actress in an effort to "protect her" from her own mental health struggles. Jilly Rizzo, one of Sinatra's closest aides, told author James Kaplan, "Yeah, Frank wanted to marry the broad. He asked her and she said no."