|Intimacy Level:|| Makeout session (Hell-O)|
|Dating Status:||Never dated|
Will and Emma try to begin dating, but many things stand in their way of their relationship, including Shelby Corcoran. Will goes to talk to Shelby because he is suspicious about one of her students, Jesse St. James, who has started dating Rachel. The episode jumps to Will and Shelby heatedly making out on a couch. Shelby decides to pull back when she finds out he was just recently divorced and having girlfriend issues, claiming he needs to focus on himself being single, not with other women. Shelby asked Will if he was gay, since most of the show choir directors she makes out with turn out to be gay. She tells him to give her a call when he's sorted everything out and calls their make-out session "hot."Once it's revealed that Shelby is Rachel's mother, Shelby confides to him that when Rachel had shared the story of how she gets thirsty when she is sad, she missed out on so much with Rachel. She says that she wants her little girl back. Will tells her that if she really cares about Rachel, that she has to tell Rachel what she just told him.
Shelby gets hired at McKinley, starting up another Glee Club called The Troubletones, and tells him that she won't take any of the New Directions away from him.You and I/You and I to show them that putting two great things together can make them even better, no matter how different they are, implying the glee clubs.
Will's glee club, New Directions and Shelby's glee club, The Troubletones, face off at sectionals. New Directions performs a Jackson Medley (ABC, Control and Man in the Mirror) while The Troubletones perform a mash-up, Survivor/I Will Survive. In the end, New Directions triumphs, winning Sectionals, leaving Shelby and The Troubletones unhappy. Mercedes, Sugar, Santana, and Brittany all return to New Directions.
- A student has had a crush/close-relationship with/on each of them. (Puck had a crush on Shelby and Rachel on Will).
- Both have worked as teachers at William McKinley High School and respectively, both Glee Club directors.
- Both have coached Glee Clubs.
- Both have had a duet with Rachel.
- Both thought they'd be parents of Beth at some point.