In 1985, Robbie Heart (Adam Sandler) is a wedding singer from the town of Ridgefield, New Jersey. Engaged to his long-time girlfriend, Linda (Angela Featherstone), he meets and befriends a waitress, Julia Sullivan (Drew Barrymore), at the reception hall where he is performing one night. Julia is also engaged, to fiancé Glenn Gulia (Matthew Glave).

On his wedding day, Robbie is devastated when he is left standing at the altar and tries to soldier on, but his despair hinders his performances. Julia tries to cheer him up, and later asks him to help her plan her wedding. Initially reluctant, Robbie eventually agrees, and their friendship blossoms as they spend more time together and become closer.

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