They started dating in Sexy, but broke up in A Night of Neglect, the fifteenth and seventeenth episode of Season Two, respectively.
Holly takes over the Glee Club while Will is sick. Will does not approve of her teaching style, but she defends it. He respects her defense although he still doesn't agree with it. He invites her over to his apartment to talk where Holly reveals how afraid she is of commitment and how a traumatic experience in the past where she was punched in the face by a student caused her to loosen up and stop taking the world so seriously. Terri comes to Will's apartment while Holly is over and immediately assumes that Holly is Will's girlfriend. Even though he is not dating Holly, Will tells Terri that he is done with her, and Holly remarks that Terri is "a bitch." At the end of the episode, Will asks Holly to help modernize Singing in the Rain with him, and she agrees, mashing up the song with Umbrella. The song, Singing in the Rain/Umbrella is performed at the end of the episode with New Directions. (The Substitute)
Will is seen to be absolutely overjoyed that Holly is returning as the Sex Ed. teacher. He greets her, exclaiming that he has missed her face. Will later rehearses a rendition of Prince's Kiss with her, culminating in a kiss. Right after the kiss, Will tells Holly that "[he's] so into [her]." Holly turns down his advances, explaining that she is damaged goods, and she would only end up hurting a nice guy like him. Holly is dismissed from her teaching position due to parental complaints about her classes. Before she leaves, Will meets her in the auditorium. Holly says that seeing another woman have the hots for him makes her want to learn about romance; he offers to teach her, remarking that he is "an excellent teacher," and they kiss. (Sexy)
Will is talking to Holly on his cell phone, telling her about Regionals, and how great the Glee Club is. Will also tells Holly that he loves her "too" in this episode, implying that Holly had said, "I love you." (Original Song)
Will sees Dustin Goolsby attempting to flirt with Holly and insulting his hands as tiny baby hands. Will gets jealous, but immediately catches himself, and says he's not the jealous type. Holly responds with, "Neither am I." Holly is seen sadly watching Will help Emma clean her grapes, and after this, Holly sings Adele's Turning Tables at the New Directions' "A Night of Neglect" benefit for Will. Will doesn't take the hint, and Holly has to tell him that the song was for him. She reveals that she has taken a new teaching job for French in Cleveland that will last up to four months. Holly breaks up with Will before she leaves. She tells him that he knew it was going to end this way, and that she lives the "glamorous life" of a substitute teacher, but it was fun while it lasted. Holly also tells Will that he is her longest relationship. She promises that she will return to visit. She leaves the school and tells Will that Emma still loves him. It is believed that she really did love him, but she knew how much he loved Emma more, so she left him for that. (A Night of Neglect)
Upon learning that Glee club will be disbanded, April gets Holly to come to Lima. Will is surprised to see that they know each other and they inform him that a Facebook page with all the guest that have been in the glee club exists. Holly and Will then perform Happy with April, the New Directions and Alumni. (100)
April and Holly are sitting in the teacher's lounge, playing "kill, marry or bone" with Will, Figgins and Brad. Holly admits she'd bang Will while marrying Figgins and pushing Brad off a cliff. The next day, Holly tries to convince Will of April and her idea to shoehorn music into McKinley's extracurricular clubs. They attend the Animal Husbandry club and after offending its actual members, she proceeds to perform Party All the Time with back-up from Blaine, Kurt, Mike, Quinn, Rachel, Puck and Will.Sue calls both Holly and Will into her office and presents them the hate-mail and letters of complaint she received due to Holly's behavior in the Animal Husbandry club. Sue officially puts an end to all glee club-related intentions at McKinley. Will admits defeat and tells a resistant Holly that he's accepted glee club's fate. Will walks away and Holly approaches Artie and together, they create a video of the New Directions members past and present, as well as Holly herself and Sue, talking to Will's unborn child about what their father has achieved and done for each and every single one of them, effectively moving Will to tears. In the video, Holly recalls how Will and her hooked up a couple years ago and that she could've been the kid's mom. (New Directions)
- Related Songs
- This is the third shortest relationship on Glee after Jitty and Puckleberry, only lasting three episodes.
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