Even though they both go to the same school and share some of their classes, they never really interacted until recently, following the murder of Cheryl's twin brother, Jason. While the two can be called 'friends', Cheryl has tried to flirt with him on several occasions, but as Archie doesn't have that kind of interest in her, he quickly shut her down and changed the subject.
After Cheryl tried to commit suicide by drowning herself at Sweetwater River, Archie saved Cheryl's life by performing a CPR on her.
Following the illicit affair that Archie and Miss Grundy developed during the summer vacation, they both hear a shotgun the morning of July 4th since they were there at Sweetwater River during Jason Blossom's disappearance. However, they both stayed silent in fear of their forbidden relationship being exposed. As Jason continued to stay missing, his sister Cheryl was left traumatized by the accident, and Archie continued to feel guilty about his secrecy.
In the after-party of the semi-formal, Cheryl invited Archie, Betty and Veronica to her after-party, in which she forced Veronica and Archie to make out for 7 minutes in the closet during a game, Seven Minutes in Heaven, knowing it would cause friction between Betty and Veronica. They ended up kissing against their better judgment, and returned to the party when Cheryl gleefully informed them that Betty had fled.
During biology class, Cheryl was paired with Archie. Archie asked her if she's okay, but she appeared to be slightly disturbed as she now knew that her brother was dead (Kevin and Moose discovered the body with a bullet hole in the head). Despite knowing that her brother's autopsy was currently taking place, she was willing to dissect a frog with no trouble, shocking Archie and her friends.
Later during the football game, Archie was seen running with the rest of the Riverdale Bulldogs. Cheryl noticed the number on his shirt, number 9, that was once Jason's number in the team. It became too much for her, causing her to run away after realizing that her brother was truly gone and would never return again. Veronica follows her to the girl's locker room and embraces her in a comforting hug.
The next morning, after Cheryl had explained what she meant by being guilty, Archie decided to tell the police that he'd also heard the gunshot that morning by the lakeside. Later on, Cheryl wanted to repay Archie for corroborating her gunshot story. She asked Josie for a favor who then allowed him to observe the Pussycats’ rehearsal for the upcoming Taste of Riverdale event at which they're going to perform.
As Archie tuned his guitar that morning in the music room, Cheryl entered with an invitation for him to escort her to her family's annual event, The Tree Tapping Ceremony. It was the start of maple tapping season, and The tree tapping ceremony was an extremely exclusive annual ceremony that honored the Blossom bloodline. The maple tapping was something special that she and Jason had done together ever since they could walk, but she was not sure she could face it alone this year, if Archie came along as her escort, maybe she could get through it. Admittedly, Archie would love to help her, however, he could not accept her invitation because he had a girlfriend, though he suggested that she ask Kevin or Reggie. Unfortunately, Cheryl did not want Kevin or Reggie, she desired Archie, he was the only person to defend her against Sheriff Keller, even when her parents did not.
Later on, Cheryl's mother, Penelope, met up with Archie and made him an offer he couldn't refuse. She offered to put a word in his behalf for a spot in the exclusive summer music program at the Brandenburg Music Academy since Cheryl's great-uncle Harrison sits on the board. Brandenburg Music Academy was a school for the musically gifted, though hard to get into, so Archie was really happy. However, that would only happen if he reconsidered escorting Cheryl to the tapping. Penelope recalled how Archie brought her Jason's football jersey during his memorial, that was a gesture of kindness during a moment of despair for her family, making Archie a good person in her eyes. Penelope insisted that Archie escort Cheryl, it would only be an afternoon and it would mean the world to Cheryl, which Archie finally came around to agree to.
The next day, as the tree tapping ceremony was ready to commence, all Archie had to do was hold the bucket steady, Cheryl would do the rest. Archie wondered who all the unfamiliar guests were and Cheryl explained that they were her father's board of trustees. They were worried that Cliff was loosing his grip on the company, and if this was to be proven true, they would join together to steal it from him. Jason's death was a PR debacle, Polly being pregnant and unwed definitely did not help the situation.
Cliff was holding his speech with Penelope standing next to the maple tree. Cheryl was called to stake the tree, dragging Archie with her to the tree. Cheryl was nervous, as she'd only seen Jason do it, but she'd never done it herself. Archie, who was holding the bucket, gave Cheryl a pep talk, telling her she could do it in her sleep, and just like he said, she did it without a hitch. Everyone applauded Cheryl and her parents smiled as well. The ceremony ended as they all stood for a group photo.
Following the group photo, they were walking back to the Blossom Maple Farms. Aunt Cricket and Uncle Bedford were not convinced that Cheryl couldn't be the successor of the business. Hearing how aunt Cricket and uncle Bedford were insulting Cheryl, Archie came to her defense, informing them that Cheryl loved Jason, she did as much to help the Bulldogs win as he did, she also had a 4.0 GPA, so if there was one thing that he learned from Cheryl, it was that she should not be underestimated or betted against.
On Cheryl's behalf, Cliff asked Archie to escort her to the Blossom Banquet later that week, and while Archie initially denied their invitation, Cheryl soon joined them and convinced him that she needed a dance partner. The next night, Cheryl paid the Andrews a late night visit, she wanted to gift Archie with a brand new guitar to show her appreciation for him agreeing to escort her to the banquet. Before leaving, she commented that her claustrophobia acted up in small houses and she kissed Archie on the cheek. As promised, Archie escorted Cheryl to the banquet that week. As everyone gathered at the dinner table, Cliff held his speech. After the speech, Cheryl told Archie that her parents kind ways were not genuine as they wanted her to fail the tapping.
Following an argument with her father, Cheryl exited the banquet for some fresh air, she was of course followed by Archie. Jason was the golden boy, Cheryl said, people hated her, and while that was fine at school, it was too much to bear from her own family. However, Archie thought she was awesome, which led Cheryl to express how she felt that Archie was the only decent person left in Riverdale. Cheryl then kissed Archie, taken by surprise and told Archie that her lipstick was maple-red, in case he was wondering why it was so sweet. All Archie could do was walk off. Cheryl managed to catch up to him on the other side of the lodge after he ran off, she thought it was Cinderella that ran away from the ball, not Prince Charming. Archie wanted to break off their arrangement, but Cheryl first reminded him of everything he would be losing if he did. She then accused him of being just as bad as everyone else in town, despite her initial beliefs, as he wanted something from them as well.
Cheryl, devastated by the death of both her brother and father, decided that she didn't want to live without her brother. She went to Sweetwater River where she tried to break through the ice. However, Archie and his friends arrived just in time. As they screamed for her to stop from the river's edge, the ice gave way sending Cheryl plummeting into the icy water. Archie ran across the river before frantically looking for her along with his friends. He found that she had been swept away by the current, but was able to locate her quickly. He then started punching the ice repeatedly until it started to crack, his own hand gushing blood. He was able to break the ice and pull her out, before giving her CPR to resuscitate her. He succeeded and carried her off the river. Due to him punching the ice, he broke his hand.
Archie: "Forget them, Cheryl. Forget what they think. I think you're awesome."
Cheryl: "Oh Archie. Sometimes I think you may be the only decent person left in Riverdale. The only person who doesn't want something from me or doesn't want me to apologize for who I am... Or what I want."