Never Have I Ever(2009)

Charlie Brandis leads a quiet and uneventful life as a wallflower. His parents trust him, his friends like him, girls are indifferent toward him. Then there's the girl he's watched from afar, Annie Briggs, who doesn't even know he exists. Until today. For today, the powers of fate conspire against him when jock friend Gary decides to throw a party at Charlie's house because the Brandis parents are away; a party specifically orchestrated to do one thing, put Charlie and Annie (who is unaware of this plan) together. The wrench comes in the form of Gary's older sister Margot, a girl who Charlie has also loved from afar, and who might be interested in him as well. The question is, when will Charlie stop doing things because other people want him to and take stock in his own situation.