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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.Eli Gold has taken Alicia's phone from her and he deletes the second message.However, Diane and Will are also shown to be each other's confidantes in Season 1.

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He also has several girlfriends throughout the series.

Throughout the series, Will shows an attraction to Alicia Florrick.

In the episode "Heart", Will and Alicia share a passionate kiss in his office as Alicia is comforting Will after a case. Realizing she has made a mistake, she does return, only to have missed Will because he had stepped out.

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.

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