|Intimacy Level:||Ex-Boyfriend and Girlfriend, Sexual (implied in A Night of Neglect)|
|Dating Status:||Broke up in A Night of Neglect|
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 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 Singin' In the Rain with him, and she agrees mashing up the song with Umbrella. The song is performed at the end of the episode with New Directions.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.
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".
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. This is the last time we've seen Holly so far.
Sang Together (In a Group Number)
|Singing in the Rain/Umbrella||The Substitute||Artie|
- Forget You by Cee Lo Green. (The Substitute) - Holly performs this song with the New Directions in the choir room, wheras Will won't let the club perform it when being asked by Puck.
- Do You Wanna Touch Me (Oh Yeah) by Gary Glitter. (Sexy) - Holly performs this song with the New Directions, while a defeated Will looks on.
- Turning Tables by Adele. (A Night of Neglect)
- Shortest relationship on Glee so far, along with Jitty, only lasting three episodes.