Henry Roth (Adam Sandler) is a veterinarian at Sea Life Park on the island of Oahu who has a reputation of womanizing female tourists.
He shows no interest in committing to a serious relationship and his closest friends are Ula (Rob Schneider), a marijuana-smoking Islander; his assistant Alexa (Lusia Strus), whose sexuality is unclear; and Willy, his pet African penguin.
One day Henry’s boat The Sea Serpent, breaks down while he is sailing around Oahu. He goes to the Hukilau Café to wait for the coastguard. There, he sees Lucy (Drew Barrymore), a pretty girl who makes architectural art with her waffles. Henry assumes she is a local, which prevents him from introducing himself but the next day he comes back. Lucy and he hit if off instantly and she asks him to meet her again tomorrow morning.
When Henry goes back to the café, Lucy shows no recollection of ever meeting him.