Dean Martin's surprise 44th birthday party in Las Vegas turned into a memorable event for all the wrong reasons. A slightly tipsy Marilyn Monroe made a bold move by wrapping her arms around Frank Sinatra. Witnesses recall her playfully urging, “Come on, Frankie, let’s make out for the photographers.” Sinatra, ever the cool customer, quickly distanced himself from the actress and instructed one of his bodyguards to keep an eye on her. It was a moment that captured the complicated dynamic between these two iconic figures.
The Complicated Relationship Between Marilyn and Frank
Marilyn Monroe’s relationship with Frank Sinatra was as complex as it was intense. After both had gone through painful divorces—Marilyn from Joe DiMaggio and Frank from Ava Gardner—they found solace in each other. They bonded over shared struggles with insomnia, loneliness, and insecurity. As Marilyn once confided to gossip columnist Louella Parsons, “He has always been very kind to me.” Some even suggest that Frank became so deeply invested in Marilyn’s well-being that he proposed marriage. Actress Ruta Lee, speaking at the Edwards-Lowell Gallery and Andrew Weiss Gallery's "Marilyn Monroe: 17 Years in the Making" opening night, described Marilyn as "a soft little pussycat that needed to be protected."
From Casual Encounters to Deep Connection
Their relationship began casually in the late 1950s. According to Marilyn’s maid, Lena Pepitone, the star even moved into Frank’s L.A. home briefly to recuperate after her split from Joe DiMaggio. By 1961, their romance had intensified. “They spent a lot of nights together,” remembered Jimmy Whiting, a close friend of Sinatra’s. “They took bubble baths together.” Despite their growing intimacy, Frank tried to keep things under wraps out of respect for Marilyn's ex-husband. “He didn’t want Joe to get pissed off,” explained insider Jim White.
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A Turbulent Yacht Trip
In August 1961, Frank and Marilyn hosted friends aboard Frank’s yacht, but things didn’t go smoothly. Marilyn was reportedly struggling with substance abuse and drinking heavily. “She was giving him a hard time… taking a lot of drugs and drinking,” revealed an insider in J. Randy Taraborrelli's book Sinatra: Behind the Legend. Although Frank reportedly threatened to “throw her right off that boat,” he couldn’t stay mad at her for long. “Marilyn was real dependent on Frank,” explained Jimmy Whiting. “She used to say, ‘If I have any problem, there’s only one person I know can help: Frankie.’”
A Brief Engagement and Distance
In February 1962, Frank shocked everyone by announcing his engagement to dancer Juliet Prowse. Even his closest friends were surprised. “I do think it had to do with Marilyn in some way, maybe trying to break from her a little,” said Sammy Davis Jr. But the engagement was short-lived, lasting only six weeks. It was clear that Frank needed space, but his heart wasn’t entirely in the relationship.
Final Efforts to Help Marilyn
In August 1962, Frank invited Marilyn to the Cal-Neva Lodge in Lake Tahoe. Security guard Joe Langford remembered Frank’s concern upon seeing how depressed Marilyn seemed. Frank went out of his way to ensure Marilyn was comfortable, arranging for special meals to be sent to her room. Manager Milt Ebbins even suggested that Frank proposed to Marilyn during this time. “He loved her and he would have done anything to save her,” Ebbins said.
A Tragic End
Tragically, Marilyn couldn’t be saved and died just one week later from an apparent overdose. Frank was devastated. “Frank was in shock for weeks,” recalled his valet George Jacobs. The situation worsened when Joe DiMaggio barred Frank from attending Marilyn’s funeral. A heartbroken Frank confided in a friend, “I loved her too. No one can say I didn’t love her too.”
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