Judy Garland & Frank Sinatra
Sinatra and Judy Garland remained good friends up until her death in 1969, but on only two occasions were the two legendary singers romantically involved. The first was in 1949, when Garland was recovering from a nervous breakdown and the two went on a romantic rendezvous in the Hamptons (Garland was still married to director Vincente Minnelli). The second was during one of Garland’s many separations from her third husband Sid Luft in 1955. Sinatra had just come off his messy separation from Ava Gardner and was spotted in Garland’s company until Luft found out.