The Baxter (2005)

Elliot Sherman (Michael Showalter) has had terrible luck with women during his life, losing three of them to ex-boyfriends in outlandish situations. Now, a week before he is to marry Caroline (Elizabeth Banks), she mentions an old high-school boyfriend, Bradley (Justin Theroux), and Elliot worries that the curse is about to strike again. A co-worker named Cecil (Michelle Williams) attempts to reassure him, but trying not to give in to anxiety only makes things worse.