An intimate love letter written by the late Judy Garland to Frank Sinatra is set to be sold in an online auction of entertainment memorabilia.

The four page handwritten letter, which dates back to 1949, is expected to fetch a price of over $4,000.

Sinatra and Garland are known to have had two romantic encounters during the course of their lifelong friendship. The first of these took place in 1949 when Garland was recovering from a nervous breakdown.

At the time, she was struggling with addiction to pain medication, sleeping pills and alcohol and had been admitted to a hospital in Massachusetts after being fired from a film adaptation of Annie Get Your Gun.

Following her recovery, which unfortunately proved to be only temporary, she engaged in a romantic rendezvous with Sinatra in the Hamptons while she was still married to director Vincente Minnelli.

The letter up for auction at RR Auction relates to that short but well-reported encounter in the Hamptons and reads in part:

“Darling, My sudden departure is a complete surprise to me. And I’m deeply dissapointed to have to miss our Monday & Tuesday date.

However it’s 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. But darling—that’s so unimportant compared to the great amount of happiness you’ve given me.

“I shan’t forget the hours we’ve 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 God’s 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… Goodbye my darling—I hope we see each other soon.

“Please don’t forget about me. Think about me because I shall be thinking of you.”

Their friendship blossomed into romance once more in 1955, while she was separated from her third husband, tour manager and producer Sid Luft.

The couple eventually divorced in 1965.

Despite her struggles, Garland continued to captivate audiences with her performances and her signature song, “Over the Rainbow,” remains one of the most popular songs of all time.

Sadly, Garland’s lifelong battle with addiction came to a tragic end in 1969 when she died as a result of an overdose of barbiturates.