 In " How a Bill becomes a Law , " Ron meets Diane Lewis ( Lucy Lawless ) who had been ignored when asking about filling in a pothole . Ron becomes a friend of hers and , in " Halloween Surprise , " he takes her two daughters out trick @-@ or @-@ treating and they begin dating . In " Women in Garbage , " while babysitting Diane 's daughters , he admits to Ann he loves Diane . Later in the episode , she admits she also loves him . In the fifth season finale " Are You Better off ? , " Andy is talking to Ron about a pregnancy test he found when Diane comes in and says she needs to talk to him , leaving the question if she is pregnant in a cliffhanger . 
