Before the start of the series, Will became estranged from Sam after Will told him how he honestly thinks his then-fiancée Ginny is "morose and controlling and icy". Sam and Ginny got married anyway and his relationship with his brother never recovered. Will recalls how Sam would leave family events early to avoid him, and cut off all contact with him, effectively breaking the family apart.
The straight version of Will
In 1999, while Will and Grace are at the mall, she bumps into Sam and urges him to come by Jack's party where Will will be. During the party, Sam opens up to Will saying he and Ginny are getting a divorce. Will, however dismisses him and leaves. Grace consoles Sam and they end up sleeping together twice that night. After Will finds out, he becomes furious at his brother telling him to "stay out of [his] room and away from [his] toys" because Grace is his property. Before Sam leaves, Grace tells him to give it time. Karen and Jack later tell Will and Grace that she slept with Sam because he is the straight version of Will and Will is mad at his brother because Sam gets to share a part of Grace that he never will.
During the final season, Will and Sam attends the Christmas dinner at their parent's house. By this point, Will and Sam are already been in good terms that Will is delighted about Sam's daughter Casey. Sam, whose divorce has just got finalized, confesses to Grace that he is terrified of starting a relationship again and they agree that after a year they would meet again and see where they are then.
- Big Brother is Coming (Part I)
- Big Brother is Coming (Part II)
- A Little Christmas Queer
- The Mourning Son
My mother was never good at accepting gifts. When I was in the fourth grade, I made her an ashtray. She said, "Great. Now I've got to get you something." — A Little Christmas Queer