Cocktail (1988)

Bent on becoming a successful millionaire, ambitious ex-military man Brian serves drinks at a New York City tavern and studies for his degree while waiting for his big break. Then, veteran bartender and cynical mentor Doug enters the picture, convinced that their chemistry and flamboyant tricks behind the bar will soon make the dynamic bartending duo famous and rich. But all good things must come to an end. As Brian tries to raise money in Jamaica to open his dream bar, a chance encounter with beautiful young waitress Jordan leads to a whirlwind romance and heartbreak. After all, love is a delicate thing. Is Brian sure he wants a future with Jordan?