JANET JACKSON & MATTHEW MCCONAUGHEY

After hitting it off while sharing presenting duties at the 2002 Grammys, the pair denied rumors of a romance, but both later admitted to a fling. “He is such a great guy and such a sweetheart,” the “Escapade” singer, 55, said in 2006, adding, “It was just for a minute.” In 2019, the 52-year-old Dallas Buyers Club star corroborated that the affair was short-lived. “We went and had dinner one night,” he told Andy Cohen. “That was sort of it.”