When Arctic marine life veterinarian Henry Roth (Adam Sandler) isn’t tending to the sea animals at Sea Life Park in Hawaii, he’s breaking the hearts of mainland tourists in search of a vacation romance. A long-term relationship for Henry is out of the question. It would scuttle his 10-year dream of sailing to Alaska to study the underwater life of walruses. Henry is close to making his dream come true when his schooner, the Sea Serpent, suffers a mishap during a trial run, which lands him at the Hukilau Café. He’s immediately smitten when he sets his eyes on one of its patrons, the beautiful young Lucy Whitmore (Drew Barrymore), who is seated alone, having breakfast.
Intrigued, he returns to the Hukilau the following day. Lucy is again seated alone with her waffles. Henry joins her and as they chat, he becomes more and more interested. Ignoring his own rule about dating local girls, he makes a date to meet her for breakfast the next day. But when he arrives and makes a reference to their previous conversation, she thinks he’s some kind of freak and calls for help. Lucy has no idea who he is. And Henry realizes that if he wants to win her affections, he’s going to have to start over again every day for the rest of his life.