Frank Sinatra and Judy Campbell Exner
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When Frank started dating Judy Campbell, it was because he thought she was an extremely attractive woman and would be easy to bed, as long as she was treated like a lady. Frank introduced her to his lifestyle of night long parties and drinking.

One night, Frank brought paid escorts into their bedroom – an act also done by JFK in later years - terrifying Campbell. Judy wanting to end the relationship, fought with Frank and his response to the incident was, “How was I supposed to know?”

Frank’s mistake in the bedroom cost him his relationship with her, but also sparked a friendship at the same time, as Judy wasn’t banished from the Sinatra friendship circle for her outburst. Frank was the one that introduced her to JFK during his campaign for presidency, knowing that the President would be taken with her.

Over the next couple of years, Frank would find himself, on occasion, back in the arms of Judy for old times sake, and the fact that she admits she was drawn to him, even after what he’d done.