Emily is Blair Waldorf's cousin and she is coming to stay with Blair for awhile. Chuck makes a bet with Nate that he can make her fall in love with him. But Emily is very stubborn and it takes awhile for him to even get a date with her. Emily starts to gain feelings but so does Chuck and he gets obsessive and protective over her. But then Blair finds out about the dare and she tells Emily. Emily ignores Chuck. Will Chuck admit he actually has feelings? Will Emily take him back?