Denise Richards (Lisa)
Most people can recall Denise Richards from Starship Troopers. She played the main character’s love interest, Captain Carmen Ibañez, who ditched her high school boyfriend to attend pilot school. Well, she was also on TAAHM and left quite an impression on a younger Charlie Sheen.
She originally stayed with Charlie in his house but moved out since he wasn’t looking for a serious relationship. After letting him know that she was getting married, Charlie invites her to move back in, but things don’t quite work out. In the end, they break up for a second time because, again, he has commitment issues.