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The story of this season still revolves around the five main characters. Matthew (Jason Segel) and Lily (Alyson Hannigan), who have been dating for nine years, finally decide to get married. While they are busy preparing for the wedding, the soon-to-be bride Lily suddenly goes to San Francisco to study art without saying a word, forcing Matthew to cancel the wedding. Three months later, Lily returns to New York and wants to reconcile with Matthew. Will Matthew, who has been deeply hurt, forgive Lily? On the other hand, Ted (Josh Radnor) and Robin (Cobie Smulders), who have mutual feelings for each other, finally understand their true emotions after going through various events and ups and downs, and decide to be together. Meanwhile, the playboy Barney (Neil Patrick Harris) continues to enjoy his single life. However, in other aspects, he remains mysterious. Ted and the other four discover that they actually don't know Barney well, and they all start to become curious about Barney...