Then and Now: The Women of "Two and a Half Men"

Then: Courtney Thorne-Smith

The character of Lyndsey shows up several times in Two and a Half Men. She’s played by Courtney Thorne-Smith, and has an on again off again relationship with Alan from season 7 and on. They broke up and got back together countless, countless times! Lyndsey’s son, Eldridge, happens to be Jake’s best friend. Lyndsey has always loved Alan, but she’s an alcoholic and has a hard time not hooking up with other men while she’s with him.