Despite the 15-year age difference and starkly different backgrounds between Michael Bolton – a Jewish soft rock star from Connecticut — and Ashley Judd — a Hollywood actor who comes from a family of country music stars – the two seem to have actually dated for a few years back in the ’90s. Although the exact timeline is fuzzy, it’s fair to suspect something was going on when Judd starred as the female lead in Bolton’s 1997 sultry music video for “The Best of Love,” a song which he co-wrote. “All I’m askin’ is to keep you near forever, just ’till the end of time,” Bolton sang, evidently to Judd. “My heart is overflowing … I wanna spend my time, spendin’ time with you, baby.”
Judd seemed to have been crazy for him in return, too. “I’m so swept away that, as far as I’m concerned, the rest of the world doesn’t exist,” Judd told Harper’s Bazaar in 1997 (via The Spokesman-Review). “I’m not really conscious of anybody but him.” Judd even called him “family,” adding that he was “very sweet,” according to Glamour.
Though the video — and lyrics — were rather suggestive, their relationship would not last until the end of time. While it’s unclear exactly when they broke up, it’s safe to say it happened sometime before the turn of the century, as Judd met her future husband, British race car driver Dario Franchitti, in 1999, per The Sun.
