- "You did a bad thing, daddy... And now everyone knows."
- —Cheryl to Cliff[src]
Presumably, father and daughter were close, or at least on good terms, before Jason's death and Cheryl's involvement in his plan to run away from home.
Throughout the Series Edit
When Jason's body was eventually found, Cliff, Penelope and Cheryl arrived at the morgue to positively identify it. As the coroner revealed the body, Cheryl turned away in horror, as did Penelope, however, Cliff was far less emotional than the two, mutely staring at the corpse of his son.
The night of the annual fall Pep Rally, Cliff and Penelope sat in the front row of the bleachers as Mayor McCoy dedicated the event to the memory of Jason and watched Cheryl performed with the River Vixens, accompanied by Josie and the Pussycats . Shortly after the performance Cliff became concerned as Cheryl raced off the stage crying, after seeing Archie in Jason's football jersey.
When Sheriff Keller interrogated Cheryl about the lies she had told regarding her last encounter with her brother, Penelope and Cliff interrupted in a state of anger and abruptly ended the meeting. Cliff demanded to know why his daughter was a suspect in his son's murder case. As they rushed Cheryl out of the office, Penelope wondered why Cheryl didn't contact them, to which Cliff replied that Cheryl was a liar, indicating their relationship had soured.
The day before Jason's memorial, Cheryl invited Veronica Lodge over for dinner with her family. Cliff, as well as Penelope, were rather rude to Veronica and made it a very uncomfortable meal. At the memorial the next morning, Cliff looked on angrily as Cheryl hijacked the service to speak to the guests about Jason.
After learning of Polly Cooper's escape from the Sisters of Quiet Mercy group home, and Betty Cooper's search for her, the Blossoms orchestrated a search party of their own, however, witch hunt would appear to be the more accurate term. With the news of Polly's recent escape moving throughout town, Cliff wondered if it was possible that Polly had escaped before, maybe on the day that Jason was murdered. Cheryl firmly believed this to be true. During the press conference held by Alice Cooper, they learned that Polly was pregnant with Jason's child.
Through Cheryl, Cliff and Penelope arranged a meeting with Betty at Pop's Chock'lit Shoppe hoping to further discuss the plans for Polly and the baby. Cliff and his wife were relieved to learn that they were safe. Penelope told Betty they wanted to offer emotional support and Cliff assured Betty that money would never be a problem for them. They tried to get Betty to reveal Polly's location but she refused.
It was finally the maple season, and that meant that the traditional ceremony was soon to take place. Cheryl and Jason had always gone together, but since Jason had died, Cheryl felt she needed someone to escort her to the ceremony. She asked Archie, but he denied the offer, but later accepted when Peneople gave him an offer he couldn't refuse.Cliff admitted that he didn't really react in an enthusiastic way when he'd heard that Archie was escorting his daughter, due to recent issues with Fred. However, later on, he saw that having Archie was an advantage both for his business and his daughter.
He wanted Archie to be alongside Cheryl because it created a good picture for the board and shielded the negative thoughts about Polly's pregnancy among other things. Though Cheryl was a bright girl, the trustees were skeptical of having her play an active role in the company, but if someone with Archie's character were at her side to temper her erratic behavior, they would be more inclined. Basically, having Archie with Cheryl created an appealing picture. So Cliff tried to bribe Archie so that Cheryl could and Archie could be a couple.