Complex sentence: Milano dated actor Corey Haim "on-and-off" from 1987 to 1990 and ice hockey defenseman Wayne McBean from 1988 until the Indians' 1990 Calder Cup win.
Split into simpler sentences: Milano dated actor Corey Haim "on-and-off" from 1987 to 1990. She also dated ice hockey defenseman Wayne McBean from 1988 until the Indians' 1990 Calder Cup win.