Judy Garland and Frank Sinatra were not only lifelong friends but they were also romantically involved - twice. The first time was in 1949 after Garland had been fired from the film Annie Get Your Gun (she was replaced by Betty Hutton) and was next admitted to a hospital suffering a nervous breakdown. Following her recovery, Garland (still married to director Vincente Minnelli) went on a secret, romantic rendezvous with Sinatra in the Hamptons. The second time was in 1955 when Garland was separated from her third husband, producer and tour manager Sidney Luft. She briefly resumed her romance with Sinatra, who at the time was also separated from his then-wife Ava Gardner.
Garland remained close friends with Sinatra until her untimely death in 1969. She was $4 million in debt when she died and it was Sinatra who reportedly paid for her funeral.
The following (undated) letter from Judy Garland to Frank Sinatra was presumably written in 1949, after their romantic rendezvous in the Hamptons.
My sudden departure is a complete surprise to me. And I’m deeply dissapointed [sic] to have to miss our Monday & Tuesday date. However its [sic] imperative that [I] reach Boston by Sunday. I shall be at the Ritz-Carlton either under Mrs. Vicente Minnelli or in care of Carlton Alsop.
You said today that you’d been neglegent [sic]. But darling—that’s so unimportant compared to the great amount of happiness you’ve given me. I shant [sic] forget the hours weve [sic] spent together—ever!
I’ll let you know how everything goes on this trip. In the meantime—
Take good care of yourself—be happy and have lots of fun and laughs.
And for Gods [sic] sake—keep those wheels in your lil ole head down to the minimum.
Drop me a line if you can because it will cheer me up a great deal.
I hope to talk to you tommorow [sic] —but I wanted to write this in case we miss connections. Even if we do reach one another—I’ll send it anyway. Its [sic] getting late—so I’m gonna wash up, get my money, etc.
Goodbye my darling—I hope we see each other soon. Please dont [sic] forget about me. Think about me because I shall be thinking of you.