Nick Di Angelo (Rob Lowe) is working in a Las Vegas casino to earn enough money to pursue the woman of his dreams – Lady Victoria Wingate (Amanda Pays) – to Oxford, England, where, he believes, the only way to win her is to get into Oxford University and join the rowing team. After spending the night with a beautiful older woman (Gail Strickland), he collects enough money to make the trip and arrives at Oxford in his small sporty car – which promptly gets stuck between two walls along a very narrow street. Thus begins Di Angelo's troubles in Britain.
Di Angelo is accepted into Oriel College; consequently, large parts of the film are set in the college itself.
To help him along, the coxswain of the rowing team that Di Angelo joins is also an American: Rona (Ally Sheedy). Di Angelo quickly finds Lady Victoria but also finds that she is deeply involved with another Oxford rower, Colin Gilchrist Fisher (Julian Sands), a member of Christ Church college.
Di Angelo comes to learn not only the value of friendship and love, but also the importance of keeping promises to teammates and to oneself as well as the importance of thinking beyond oneself.