Charlie has been in love with his best friend Sylvia for four years, but has always concluded that he is unfit for a serious relationship. Now that he has a suitable career and experiences of fleeting love and loss behind him, he decides that tonight is the night that he confesses his love for her. But when she tells him that another man has come into her life, he stands idly by. Over the course of one night, they recall old stories of awkward relationships, the humiliation, the guilt, the rejection, the laughter, and the wisdom that comes with age. Rekindling the spark they had when they first met, Charlie must now decide if he can remain her best friend or become something more.