#17: Lauren Bacall & Frank Sinatra
Lauren Bacall and Frank Sinatra’s engagement was brief, intense, and very gossip-column friendly. After Bogart’s death, Bacall and Sinatra became close, and their relationship seemed ready to become one of Hollywood’s great second-act romances. Then publicity got in the way, Sinatra reportedly recoiled from the attention, and the engagement collapsed. It had all the ingredients: grief, glamour, timing, pride, and a disappearing groom. Very Sinatra, really.

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