The two are set to have a dinner date in "Boom", but because Peter Florrick runs after Alicia to stop her going out, setting his monitoring alarm off, Alicia is forced to cancel.After this Will starts dating a Law student, but it is clear he still has feelings for Alicia.Will and Alicia met when they were both in Law School at Georgetown; this connection allows Alicia to get a job as a Junior Associate at Lockhart/Gardner where Will is a named partner.
Will and Alicia then start a secret relationship in Season 3.
Diane becomes suspicious of the relationship and encourages Will to end it before they become a target of the States Attorneys Office, once again lead by Peter Florrick.
However, Diane and Will are also shown to be each other's confidantes in Season 1.
This changes in Season 2 when both decide to split the firm.
When he approaches Diane with this idea, he tells her that their fellow partner Jonas Stern costs them about as much as all of the other lawyers combined.
Diane accuses him of wanting to take away the partner that votes with her.
He is a loyal friend, shown especially in his relationship with Judge Baxter whom Alicia accuses of racism after one of her young clients is sent to a juvenile detention center.
Will stringently defends his friend, until he makes the connection that Baxter has made a deal with the detention center to receive money from all those boys he sends there.
When Alicia confronts Will about the second message, he lies to her and says that he thinks she made the right choice staying with Peter.
After Alicia's discovers that Peter had sex with Kalinda, she separates from him.
However, he then calls back and tells her that he loves her and they can make a plan together.