The Love's Labours Trilogy is a series of Daria fanfics by E. A. Smith. The Trilogy was Smith's first foray into fanfiction. Its story was continued by the fanfics The Tempest and So Long As Men Can Breathe.
Warning: The following may contain plot or ending details.
Love's Labours Lost
Shortly after arriving at Raft University, Daria makes a new friend, James McCarthy, who approaches her after hearing her make humorous quips during class. A few months into their friendship, James reveals his feelings for Daria go deeper than just friendship when he nervously asks her out on a date. This unexpected development prompts Daria to recall her past relationships with Trent, Ted, and Tom, ruminating over the pros and cons of each one in an attempt to determine how to answer James's offer. Wondering what advice Jane would give her, she realizes that Jane was always bold in relationships, not fearing being hurt, and that it would be good for her to be the same.
Love's Labours in Ruins
Daria nervously accepts James's proposal, and the two of them go to see a local production of Troilus and Cressida. For a while, everything goes well, until James attempts to take Daria's hand and she instinctively draws it back, breaking the good mood for them both and sending the night spiraling downward. The date is ruined, and after the play, the two part ways, their friendship apparently ruined. Daria walks back to her dorm, wondering if her own high standards have been partially responsible for her poor history in relationships, if she destroys any friendship or romance she judges to be imperfect and therefore unworthy. She resolves to fix her now-broken friendship with James, but does not know how to do it.
Love's Labours Renewed
Daria meets James in class and, with difficulty, convinces him to talk with her over lunch. At lunch, Daria apologizes for hurting James, but admits that though she wanted to be able to see James as more than a friend, that she could not, at least not so quickly. James in turn apologizes for not giving her the time she needed, but confirms that his feelings for her are quite real. Daria tells James that he is better off not dating her, that she has a history of walling herself off from others to avoid hurt, and that eventually she would have cut him off as well. She tells him she still wants to be friends, like before, but James turns her down, saying that it would pain him too much to be around her. Daria allows James a single farewell kiss, and the two part ways. Daria resolves to break her own cycle of emotional isolation and fear, hoping that she will never hurt another person like this again.
The Love's Labours Trilogy was nominated for three Booties: "Favorite Post-Is It College Yet?", "Favorite Character Development/Redevelopment/Growth", and "Favorite New Series".