<Li> Kellie Newmark ( Cynthia Watros ) -- Drew 's childhood friend . She has had a crush on Drew since high school but never told him . She was married but her husband cheated on her with her sister . Her mother is an alcoholic and leaves her father , eventually hooking up with Lewis . After Kate leaves , Drew realizes that he loves Kellie . Drew is afraid to tell Kellie because it may ruin their friendship like it did with Kate . After Lily leaves Drew , they confess their feelings for each other . When Kellie comes out while Drew is talking to his dad and asks Drew what they are going to do about their feelings for each other , Drew 's dad falls off the roof and dies . Eventually during the beginning stage of their relationship Kellie finds out she is pregnant with Drew Jr. but wo n't marry Drew because she does n't think he is ready for marriage . During the finale she decides Drew is ready . But her water breaks and she and Drew get married right when the baby is born . </Li>
<Li> Kellie Newmark ( Cynthia Watros ) -- Drew 's childhood friend . She has had a crush on Drew since high school but never told him . She was married but her husband cheated on her with her sister . Her mother is an alcoholic and leaves her father , eventually hooking up with Lewis . After Kate leaves , Drew realizes that he loves Kellie . Drew is afraid to tell Kellie because it may ruin their friendship like it did with Kate . After Lily leaves Drew , they confess their feelings for each other . When Kellie comes out while Drew is talking to his dad and asks Drew what they are going to do about their feelings for each other , Drew 's dad falls off the roof and dies . Eventually during the beginning stage of their relationship Kellie finds out she is pregnant with Drew Jr. but wo n't marry Drew because she does n't think he is ready for marriage . During the finale she decides Drew is ready . But her water breaks and she and Drew get married right when the baby is born . </Li>
who played kelly on the drew carey show
who played kelly on the drew carey show
Cynthia Watros
Cynthia Watros