Single girl? Fine, yes. Single girl in Manhattan? Rough but okay. Single girl in Manhattan with four model roommates? Oh God. But such is the life that art restorer Amanda Pierce (Monica Potter) suddenly and unexpectedly finds herself with in this movie.
Blessed with a cut-rate deal on a luxurious Eastside apartment but stuck with four super-thin, super fabulous roommates Jade (Shalom Harlow), Roxana (Ivana Millicevia), Candi (Sarah O'Hare) and Holly (Tomiko Fraser), Amanda doesn't know whether to thank her lucky starts or curse her lot in life.
Never content to let ordinary exist, the models immediately enlist Amanda as their experiment in makeover magic, transforming her from just fine to so fierce and training her in the fine arts of attitude, accessories and avoidance of paying the cocktail tab.
Things really begin to look up as Amanda falls for Jim Winston (Freddie Prinze, Jr.) the charmer in the building next door, and Jim falls for Amanda right back. He seems to be the fulfilment of Amanda's unanswered prayers.. until one night when the girls spy him committing what appears to be a cold-blooded crime.
Amanda's life suddenly begins to unravel as she and her four loopy room-mates take to the streets of Manhattan as very amateur detectives to solve the naughty business next door, staying one step ahead of trouble and in step with the latest style.
Head Over Heels unfolds in a world of fashion and foul play where crime is wearing the wrong thing or chasing the wrong guy.