Simon is a would-be writer and a serial monogamist, with a habit of self-sabotage. He loves women but has a habit of messing up his relationships with them, despite his best efforts and starting each new relationship with optimism and genuine conviction it will last this time. ‘Four Women’ charts Simon’s life with consecutive girlfriends, one after another, over a twenty-year period. Through a mixture of his own inadequacies and hang ups as well as theirs, things go wrong, until he eventually meets the last one. Will it be fourth time lucky? The four women are Judy , a quiet, gothic teenager with hidden depths, Roxanne, stylish, and a former arts student, Claudia, gifted, but complicated and moody, and Heather an apparently easy-going indie chick. Set against the background of nineties and noughties culture, ‘Four Women’ is one man’s journey to find true love.