23. Ava Gardner
Gardner was definitely on the list. She was Sinatra’s second wife, the one who he let get away after six years. Both Gardner and Sinatra later remarked separately that they wished they’d invested more in their marriage.
22. Donna Reed
It was on the set for the film, “From Here to Eternity,” that the pair met. They sparked so much energy between them that they both earned Oscars for their work in the film. For a minute, it seemed their destiny to be together, but as is often the case in Hollywood, the affair didn’t last.
21. Elizabeth Taylor
The official word on this relationship is that it didn’t happen. If they were a couple, the two kept it behind closed doors, and it was brief. One accusation is that they did sleep together, that Taylor became pregnant from the affair, and that Sinatra pushed her to abort the fetus.