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After almost not graduating, Pacey enters life after high school on somewhat of a low note. After struggling to keep Joey's affection, Pacey's low-esteem and underachiever attitude got the best of him and led to the eventual break-up of his relationship with Joey. To make matters worse, after doing double-duty to finish classes in time for graduation, Pacey was unable to get into college. Instead he was offered the opportunity to work on a yacht, an offer he couldn't refuse. After a summer sailing in the Caribbean, Pacey eventually docks in Boston and decides to test the waters in this cosmopolitan city. New opportunities lead Pacey to become involved with gorgeous Latina barmaid Karen (Lourdes Benedicto) who has a complex past.
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