Kevin was assigned to Will by Wheelin' Dealin' since Luke thought his style would work well with Will's and because Kevin has an industry reputation as an effective songwriting mentor. Will, still closeted, fights his attraction to Kevin, although Kevin suspects that Will might be gay.

After several weeks and some successes, Will eventually goes to Kevin's house and tries to clumsily admit his feelings, but cannot quite do it. To his surprise and delight, Kevin kisses him and the two begin an intimate relationship. The pair continue to see each other as the weeks go by, and Will eventually asks Kevin if they can be exclusive until he sorts his feelings out. Kevin agrees, although reluctantly so because Will is still in the closet.

Eventually however, the paparazzi manage to get suggestive photos of Will and Kevin, prompting Wheelin' Dealin' to organize a press conference. Kevin reluctantly agrees to lie to the press to preserve Will's reputation, and his renewed relationship with his father. Will however, realizes that he's tired of living a lie, and of hurting the people he cares about (specifically, Kevin and Layla), and publicly admits he's gay.

Following this, Will's career takes a downward spiral, and he spends most of his time hiding at Kevin's. Kevin eventually persuades him to go out again, but their dates usually end disastrously: Will's usual hangouts are filled with irate fans (and former female lovers), while Will feels out of place in the gay scene Kevin tries to introduce him to. Will's frustration at his career's stall continually rears its head, but each time Kevin manages to help him, first by getting him songwriting gigs, and then by managing to get him on stage.

In spite of their difficulties, Will thanks Kevin for his support and tells him he loves him repeatedly; Will, however, doesn't seem to notice that Kevin never says it back.

Kevin's final straw comes when he gets will a singing gig at a club; Will performs well but is upset when the largely female crowd pushes a presumably gay man to the front row. Will interprets this is a rejection and drinks heavily. Exasperated, Kevin dumps him, unable to put up with Will's continued self-loathing.

Several months later, Kevin is brought in to polish up some of his and Will's songs. The two share an awkward reunion, with Will attempting to apologize and Kevin gruffly telling him that he did love Will, but that his attitude made it impossible to say it; Will is also crestfallen to overhear that Kevin has a new boyfriend he seems excited about. Otherwise, though the meeting goes well, and the pair manage to regain their working rapport.

A few weeks later, Will has finally embraced his new identity as country music's most prominent gay artist, and he and Luke ask Kevin to help stir up some local support in Atlanta, where Will is attempting to get an interview with the conservative pundit who has been attacking him in the press. The resultant street concert is a resounding success. After Will's interview, Luke notices the way he and Kevin still look at each other and encourages Will to ask Kevin for another shot. While celebrating Will's victory, Kevin mentions that he's single again, and kisses a delighted Will.

After Will suggests they move in together, Kevin looks for an apartment but does not tell the renter that they are a couple in case they are homophobic. He urges Will to have a look at one he feels is suitable but later finds the application form crumpled up in the trash. Will comes clean about not wanting them to live together and they split up.