Then: Jeri Ryan
Jeri Ryan plays Sherri. Sherri is just another woman on Charlie’s long list of girlfriends. Charlie views Sherri as the female version of himself. The two dated, but Sheri kept playing hard to get all the time, so Charlie got sick of it and broke up with her. When Charlie and Alan bump into Sherri at an optician, Alan asks her out. It doesn’t last long, though, and the two ultimately break up.