Henry Roth (Adam Sandler) lives the ultimate bachelor lifestyle in a Hawaiian paradise with endless no-strings-attached relationships...until he meets Lucy Whitmore (Drew Barrymore). Henry and Lucy hit it off instantly and sense the beginning of a serious relationship. Approaching Lucy the next day, Henry is confused when she fails to recognize him. Lucy's friends and family fill Henry in on a tragic secret: Lucy actually suffers from short term memory loss, so when she wakes up every morning, she can't remember anything that happened the day before. Henry won't let this stop him and is prepared to make her fall in love with him all over again, each and every day.