#7: Jon Cryer: The Beginning (1984)

Demi Moore and Jon Cryer met while filming No Small Affair in 1984 and developed an off-screen romance. At the time, Demi was on the rise in Hollywood, while Jon was still early in his career. Their playful, youthful chemistry on set carried into real life, and Jon fell hard for Demi.

He later admitted in interviews that he had been entirely smitten, making their relationship more meaningful for him than it may have been for Demi. She was at a stage in her life where she was moving quickly and focused on her growing career rather than serious commitments.