My Last Five Girlfriends (2009)

After his latest failed relationship, Duncan has hit emotional rock bottom. He just can't understand what, or who, has caused all of his relationships to fail. Was it something he did… or didn't do? In a final attempt to find out where it all went wrong, Duncan takes a ride through the memories of his last five relationships. He's pretended not to care about ex-boyfriends that haven't quite disappeared, disastrously attempted to give fashion advice, and even been the first to utter those three special words—nothing seems to work out, but that's all about to change.