While Jack was working as a sales associate at Banana Republic, he sees Matt but is too afraid to approach him because he's a "smarty". With the help of a headset and Will on the other line, Jack tries to talk to him but ultimately, their plan fails and Matt ultimately gives Will his card instead. Will, however, does not call him anytime soon because he knows nothing about sports.
Will & Matt
After being challenged by Grace to go out with a "sports guy", Will finally calls Matt and on their first date, learns that Matt broke up with his previous boyfriend because he was not interested in sports. Will soon realizes that he needs to pretend he know baseball as well as basketball.
It is later revealed that Matt is still closeted when he refers to Will as his brother when introducing him to his boss. Will is perturbed, but remains seeing him despite objections from Grace. Will eventually gives him an ultimatum, and dumps him.
He is later referenced when Will's father George asks about him because says he sounds like "dynamite", to which Will replies that they broke up. George then says "any guy can't make it work with you, there's something wrong with him."
|Matt:||So, what took you so long to call me?|
|Will:||That's sort of my style. I like to wait, you know, until the guy has lost all interest in or memory of me, and then I strike.|