|“||I love my girl Cheryl, so I'm doing her this solid.||”|
|— Josie to Archie, after Cheryl asked her to help him out with his music[src]|
Sometime prior to the start of the series, Josie and Cheryl befriended one another and became quite close.
At the back-to-school semi-formal, Josie and her fellow Pussycats performed in honor of Cheryl's recently deceased brother, Jason. They sang "All Through the Night", at Cheryl's behest which she claimed was the song she and Jason had been conceived to.
Cheryl also requested Josie perform at the school pep rally, feeling that her River Vixens routine needed some star power. At the end of the performance, Cheryl went up on stage and they shared a hug, before Cheryl, overcome with grief for her brother, raced off the stage, much to Josie's confusion .
When Cheryl offered Archie Andrews a favor after he corroborated her police testimony, she got Josie to help him with his music. Josie said she was only doing it because of her friendship with Cheryl.
Cheryl and the latest recruit of the River Vixens Josie, greeted Betty and Veronica as the they entered the gymnasium for River Vixens practice. With Cheryl back in action, this had Veronica questioning if she was taking the squad back from her, to which Cheryl replied that they were never really Veronica's squad to begin with. Betty was hoping that maybe Cheryl would be kind enough to allow the Vixens to help with an event to save Pop's Chock'lit Shoppe from permanently closing. Unfortunately for Betty, Cheryl did not emerge from the frozen depths of Sweetwater River, nor the flames of Thornhill only to allow her Vixens to sling milkshakes at a death-cursed diner. Her answer was a "double-cherry-on-top no."
A couple days later, with Cheryl and Melody at her side, Josie confronted Betty at Pop's during Retro Night to find out why she posted all over social media that the Pussycats would be performing a free concert at the diner. Betty explained that had she asked Josie to perform, she would've said no, so instead, she decided to force Josie's hand into performing. If Josie's mother even hears that she stepped foot in the diner, she'd be in a lot of trouble. In spite of that, Josie cared about the shoppe, and Betty knew this to be true. Josie explained that even if she wanted to help, they were one Pussycat down because Valerie had a norovirus. Luckily, Cheryl was there to fill in, commenting that if Josie can be a Vixen, then she can be a Pussycat. Josie loved Pop Tate's cheese fries, Melody noted. So, she had as much reason to want the shoppe open as anyone else. With all in agreement, the Pussycats stood on top of the roof of Pop's diner and performed Milkshake for the crowd below.
A Wolf in Sheep's Clothing
After a night of wild partying at the Five Seasons with Cheryl Veronica, Archie, Betty, Reggie, Valerie, Melody and Nick St. Clair, the Josie and the Pussycats performed Out Tonight at the SoDale Gala Opening, which was being hosted by Veronica's family. They took to the stage, and gave a wonderful performance before the crowd. However, it was during their performance that they noticed Nick headed into the back with Cheryl, who could barely walk on her own. Concerned for her well-being, the Pussycats left the stage in search of Nick and Cheryl. They discovered Nick, in one of the bedrooms, getting undressed, as he prepared to rape Cheryl, who was barely conscious. Fortunately, the Pussycats arrived in time to save her. They pulled Nick away from Cheryl, and like a pack of wild animals, savagely attacked him. As Veronica, Melody, and Valerie made sure that Nick suffered for his actions, Josie checked on Cheryl to ensure that she was unharmed.
After the open house, Josie headed back to the Pembrooke with Cheryl, Veronica, Archie. They were joined by Betty soon thereafter. In Veronica's bedroom, Archie asked where Nick was in that moment, though Cheryl instructed him to put his cape away because the Pussycats had already saved her. Cheryl then announced that she would be pressing charges because she wanted Nick to be held accountable for his actions, for him to pay and suffer for what he tried to do to her. Cheryl began to sob, and so Josie and Veronica held her close, attempting to provide comfort for Cheryl in her time of need.
At school, Josie and Cheryl spoke of the Black Hood and how he had Josie's mother on edge, which in direct response had Josie on edge. Josie couldn't handle stress, as it affected her vocals, causing her to lose her voice. On top of that, she felt guilty about going behind the Pussycats' backs by working on songs alone, rather than working on songs with them. Cheryl understood why she felt guilty, as the Black Hood was going after sinners and Josie felt that she was sinning by sneaking around. She was allowed to feel guilty, but only up to a certain point, Cheryl remarked. Cheryl revealed that she gave Josie song "Milkshake" to a music producer, and he insisted that Josie come in alone for studio time. Josie was ecstatic to hear the news. She then opened up her locker to find a teddy bear on the top shelf, with a note tied to it. Cheryl commented "OMG, another note from your secret admirer!", but Josie wasn't pleased to see yet another note, making it the third gift this week. She needed to get a new lock. Teasing Josie, Cheryl wondered who this "mystery bae" could be. Maybe it's the Black Hood, he loves writing notes, Cheryl joked. Josie didn't think it was funny.
Josie told Cheryl in Biology class that she had been asked out on a date by Chuck Clayton. Cheryl assumed that she turned him down, which Josie had, assuring Cheryl that she wasn't insane. On a less vile note, Cheryl reminded Josie that they had a date with the recording studio after school, which Josie didn't seem too enthusiastic about. She was heading straight to the girls locker room after school for eucalyptus steam as her throat had been sore. However, they needed to practice, Cheryl stated. Josie exclaimed that she didn't know who more more controlling between Cheryl and her mother. Cheryl was sorry for overstepping her boundaries, as she could see Josie's frustration, but Cheryl explained that she was grateful towards Josie for saving her from "Nick St. Creature", adding that it was a debt that she would never be able to repay. What she could do was offer her humble skills to make Josie's career blossom. But she was happy to take a step back if Josie was feeling overwhelmed.
The next day at school, Cheryl was disturbed by the news that Josie's mother had been receiving death threats ever since the dawn of the Black Hood. Hoping to relieve Josie of her stress, Cheryl suggested that they bail on practice, but Josie would rather sing given that it would keep her mind off the prior night. Speaking of which, Cheryl couldn't believe that Josie went on a date with Chuck. Josie insisted that he was trying to be a better person, but Cheryl denied the notion, stating that taking a few art classes does not make him a saint. Furthermore, she questioned why Josie hadn't told Sheriff Keller that Chuck was stalking her. Josie explained that she was giving him the benefit of the doubt. They then entered the music room to find a drawing of Josie that read "IF I CAN'T HAVE YOU NO ONE CAN". Along with the picture was a present. Josie opened the box to find a pig's heart inside. Cheryl abruptly exited the music room, pushing Archie and Jughead out her way as she entered the student lounge, where she confronted Chuck. While some people may have been buying into his good guy act, Cheryl believed that he was the same Chuck that viewed woman as playthings to possess and torture. If the Black Hood wasn't by Cheryl's account an old white man, Chuck would be a prime suspect as far as she was concerned. Mr. Svenson, the school's janitor, interrupted their argument to ask if everything was alright, during which time Cheryl accused Chuck of threatening Josie. As Mr. Svenson asked Josie if this was true, Cheryl whispered in her ear that Chuck could also be responsible for sending her mother the letters. Hearing this, Josie confirmed Cheryl's claims, resulting in Mr. Svenson escorting Chuck to Mr. Weatherbee's office.
It was later revealed that Cheryl was, in fact, Josie's secret admirer. That night, while listening to Josie's music, Cheryl drew a picture of herself and Josie, which showed striking resemblance the drawing Josie had previously received along with the pig heart, which Cheryl was quick to blame Chuck for. Unbeknownst to Josie, it was Cheryl who gifted her with the drawing and pig heart in order to push Chuck away.
Later that night, Josie and Cheryl sat in a booth at Pop's, where Josie drank tea to soothe her throat. After getting off the phone with the Black Hood, Pop Tate announced that they were all sinners who failed his test, and that the reckoning was upon them.
On their way to class, Cheryl and Josie stumbled onto Archie and Veronica in the middle of a heavy make-out session in the student lounge. Cheryl uttered "get a room, Xenomorphs", just before she and Josie continued on their way.
In the ladies locker room, while covered with nothing but towels, Cheryl noticed the tension knots on Josie's back, which she stated was like a "sailor's rope". Fortunately, Cheryl had recently purchased lavender essential oil. She instructed Josie to turn around as she rubbed the oil onto Josie's back. Unaware that the girls were still inside, Mr. Svenson entered the locker room moments later, though he averted his eyes and apologized for the intrusion. While Josie insisted that it wasn't a big deal, Cheryl on the other hand, would beg to differ. She raised her voice and demanded that he take his male gaze and his male privilege, and get out of the woman's locker room. Referring to him as a peeping tom, Cheryl believed that Mr. Svenson should be fired and investigated. She then motioned towards Josie in an attempt to further apply the oil, but Josie pulled away.
A couple days later, in a booth at Pop's, Josie told Cheryl that she would be performing at a car dealership opening, which Cheryl remarked was barley a step above amateur porn. Reggie had texted Josie that his father was willing to pay $5,000 for her to perform five songs, so long as he got to escort her. This visibly angered Cheryl. Noticing that Jughead's father, FP had been released from prison and was now working at Pop's as a busboy, Cheryl intentionally knocked over her milkshake and demanded that he clean it up, the same way he cleaned up her brother's blood out the basement of the Whyte Wyrm. Not only did FP agree to clean up the mess, he offer her replacement milkshake, on the house.
Though they did not speak to one another, in the days leading up to Christmas, Josie and Cheryl both attended the Secret Santa gift exchange in the student lounge, along with Archie, Betty, Reggie, Veronica, Kevin, and Jughead. It was Veronica's turn, and Josie was tasked with purchasing her a gift. Veronica opened her present from Josie, which awkwardly enough was a gift certificate for a couples massage. Unfortunately, upon her purchasing of the certificate, Archie and Veronica were still together. Josie suggested that Veronica use the certificate to take someone other than Archie, such as Betty or her mother.