Frank Sinatra was the quintessential ladies man. That voice and big blue eyes was enough to get the attention of any woman and Sinatra found great thrill in the chase and the loving of women. He was known to engage in relationships with many of his leading ladies and some of the most beautiful women in the world. Click through the list to see all the beautiful and talented women that Frank Sinatra spent his time with and those who he chose to love.

Grace Kelly


Rumors of a relationship between Grace Kelly and Frank Sinatra abounded after they appeared in a movie together. There are some that claimed they dated and even had a love nest in France. But there are others that suggest a more casual relationship between the two. Frank Sinatra was good friends with Prince Ranier of Monaco and at times travels to Monaco to support Grace Kelly’s charity work.