Kevin joined Betty in her room as she prepared to see Archie after a summer spent apart. She intended to reveal her true feelings towards him that evening and Kevin offered encouragement. He reminded Betty that whiles nerves were acceptable, she must follow through. Kevin then looked out Betty's window and into Archie's next door and made a shocking discovery, "Archie got hot". Betty went over to see and while the two ogled Archie, Kevin proclaimed that Archie's abs were six more reasons Betty should confess that night.
The next day, Betty introduced Kevin to new student Veronica Lodge, who spotted Archie down the hall from them, expressing her interest, but Kevin quickly made it evident to Veronica that despite the fact that Betty and Archie weren't together, they were end-game. Later that day, at lunch, Betty, Kevin and Veronica were interrupted by Cheryl Blossom, who invited Veronica to join her cheer squad, the River Vixens. After she left, Betty revealed that she had tried out for the team the year prior, but Cheryl said she was "too season five Betty Draper", which Kevin thought was a great line, however, untrue.
That night, at the back-to-school Semi-formal, Kevin excitedly revealed to Betty that he had been propositioned by Moose Mason in the bathroom. He then went on to dance with Veronica and the two attempted to motivate Betty into finally confessing her feelings to Archie, which she eventually did, however, Archie did not return them and even went on to kiss Veronica later in the evening.
The next morning, as Archie and Betty as a couple was no longer an option, Kevin wanted to revisit his theory of Archie being gay, as he thought no straight man had that kind of body. Betty, however, wondered how Kevin was doing after he and Moose had their hook-up interrupted the night before by Jason Blossom's corpse, washed up at Sweetwater River. Betty laughed as Kevin told her he was fine and was more traumatized from having to explain to his father why he was out at the river with Moose. Later, in an attempt to make amends with Betty, Veronica presented her with gifts, however, Kevin was left unimpressed and was shocked when Betty accepted her apology.
In the student lounge while discussing Jason Blossom's death, Kevin suggested the group binge watch "Making a Murderer" on Netflix. Unfortunately, Betty had decline as she had to work on the paper. When Veronica declined as well as she had a date with Chuck Clayton, Betty was concerned as he had a reputation as a player, however, Kevin brushed her off as Chuck was "the hottest of hot".
Succeeding Veronica's date, she was slut-shamed by Chuck, and Kevin and Betty helped her get revenge. Off a tip by Trev Brown, they broke into the school after hours with Ethel and Cheryl to find a secret playbook Chuck and his friends would record their 'conquests' in which Betty then used to write a scathing exposé in The Blue and Gold, which led to Chuck's suspension.
At Pop's Chock'lit Shoppe, Jughead, Veronica, Kevin and Betty were in a booth discussing the closing of the Twilight Drive-In when Kevin noticed Archie, his father and Ms. Grundy enter the diner together. He then looked on confused as Betty quickly jumped up and pulled Archie outside.
After the Keller house was broken into and the evidence files on Jason Blossom's murder stolen, Kevin reconstructed Sheriff Keller's murder board in The Blue and Gold offices with Betty and Jughead. They were interrupted by Trev Brown, who had come by to confirm a date with Betty, which Kevin then teased her about, wondering if her mother knew about it. Betty replied that she was not on house arrest before conceding that her mother was out of town and denying she and Trev were going on a date, that he was only a source. Later, at lunch with Veronica, Jughead and Archie, Kevin once again teased Betty about Trev after Veronica remarked she was "radiating Nicholas Sparks". Cheryl then joined then to invite the group to her brother's memorial, which they all later attended.
Following Betty's sister Polly's escape from the Sisters of Quiet Mercy group home, Betty informed the group that her parents had yet to report the incident as they didn't want anyone to know that she was pregnant with Jason Blossom's baby. Archie suggested she go to the police anyways which was seconded by Kevin, who suggested they go directly to his father who would be more discreet but Jughead opposed him as his father would have to answer to the Blossoms. Betty agreed with Jughead over Kevin as the Blossoms would immediately go after Polly should they find out. However, it wasn't long before the news of Polly's escape spread, thanks to Cheryl via twitter, which Kevin alerted Betty of. In effort to find Polly before the Blossoms did, Kevin joined in on the search party throughout Eversgreen Forest to find her that Betty and Jughead organized.
During the search, Veronica and Kevin planned a night out at a club and Kevin wondered if they should invite Betty as he thought she could use a night out, however, the Blossoms, with a search party of their own, interrupted, and the search ended unsuccessfully. Betty later found Polly hidden in the attic of their house.
The next day, Kevin, Betty, Jughead, Veronica, Cheryl, Valerie, and Archie discussed Polly's current dilemma, as Betty told the group that Polly thought that no one wanted her baby. Except, Kevin remarked, the "child snatching Blossom monsters". Veronica then suggested a baby shower before Alice interrupted and pulled Betty and Veronica away.
In an effort to cheer up Ethel, whose parents had been constantly fighting, Veronica invite her over for lunch at The Pembrooke, along with Betty and Kevin. A couple days later, however, Kevin informed Betty and Veronica that Ethel's father had unsuccessfully attempted suicide after swallowing an entire bottle of sleeping pills, much to their shock.