In The Cost of Art he is seen by Tom to be a little boring, seeing him as a normal lawyer, but during their first date. He is taken by Tom to Derek's apartment, after they are called by Julia, and watch's the performance of I've Never Met A Wolf Who Didn't Love to Howl. At the end, Tom is surprised that he finds that John found his piano playing the most interesting part of the performance.
They are seen to go on another date in Let's Be Bad and, again, Tom is bored with John's lawyer talk, enough to answer his phone and forget what he was saying. At the end he asks Tom if they are just friends cause he won't go back to his apartment with him. Tom receives a call from the NYPD over Leo and asks John to come with him. John defends Leo and is able to get him off, with a warning.
In Chemistry, John invites Tom to a party at his apartment. He discovers that his mother only found out that John was gay a year ago. Tom leaves after he gets a text from Ivy. On the streets, John tells Tom that his friends liked him. Tom confronts him about him only coming out a year ago, to which he replies with "I came out when I was 8 and when I was 12 and when I was 23."
John comes to watch the Workshop of Marilyn in The Workshop, much to Tom's annoyance. He tells him that it was great, but a little hot. To which Tom 'excuses' himself.
In The Coup, John has to defend Leo in a court hearing, trying to get an incident written off. While in court, Julia gets angry at the judge, shocking him. At dinner with Tom, he tells him that he likes his 'group'. The two share a kiss.