Representation: Chris Zylka
Full Name: Jacob Calimo
Profession: Executive Robertson Enterprises
Martial Status: Broken Engagement, Paige Claus
Previous Relationships: Broken Engagement, Cassie Nova
Family Ties: Father, Shane Glubbs; Mother, Natasha Calimo; Uncle, Robbie Calimo; Grandfather, Bob Calimo
Jacob returned to Twin Peaks a young man and was reunited with Shane and Natasha. His return, however, was interrupted with Bob's car accident. The Calimo's rallied around Bob, including Jacob. Shane and Natasha, meanwhile, pressed their son for information on his engagement, as he had mentioned he had gotten engaged via an email. He remained mum but vowed that they would approve of his girlfriend. On Christmas Day, Jacob stunned his family by revealing his fiancé: Cassie Nova!
Jacob was confronted by Max, who was unsettled that his mother's fiancé was the same age as him. Jacob reassured Max that he loved Cassie and wouldn’t do anything to hurt her. Natasha and Shane, also, continued to tell Jacob that Cassie was no good for him but Jacob insisted that he knew what he was doing and just wanted their support, which he didn't get. Cassie supported Jacob and they continued to grow closer. Jacob was crushed when Bob died and leaned on Cassie for support. Jacob and Cassie continued to grow closer despite all of the reservations from Shane and Natasha. Jacob continued to tell his family that he knew what he was doing, but they were worried for him. After the trial to contest Bob's will was finished, it was Jacob's wedding day to Cassie. Cassie walked down the aisle but Shane and Natasha interrupted the wedding with the news that they wanted to be there for him. Cassie was thrilled for Jacob as this meant that their wedding would be perfect. Jacob stunned Cassie, and his parents, by revealing that he was never going to go through with the wedding as he was using Cassie the entire time to get back at her for all the horrible things that she had done to Natasha and Shane over the years. Cassie was devastated and rushed off. Shane and Natasha were pleased with their son. Cory, however, was not happy with Jacob and ripped into him for his actions. Jacob realized that he had hurt Cassie and felt bad. He tried to apologize to her, but she vowed to get revenge on him.
Jacob ran into Cassie, who admitted that she still loved him despite him leaving her at the altar. Jacob told her that they were over. Natasha suggested to her son that he come to work at Roboto, but Jacob wanted to make his own way and got a job at Robertson Enterprises, unaware that Dominick wanted to use his position there to stick it to the Calimo's. At work, Jacob was in the studio with Paige and Max, who had just broken up. Jacob and Max came to blows since Max was protective of Cassie. Jacob and Paige, however, formed a friendship and soon were dating, which made Max livid. Slowly, family members of Jacob and Paige warned them about being together since their families hated each other but they agreed to forge together in their relationship. They eventually hit the sheets. Shortly after, Jacob witnessed a moment between Paige and Max. He confronted his girlfriend, who told him that they were just friends. Max realized, however, that the way to break up Paige and Jacob was through Jacob's insecurities. Jacob continued to struggle with his insecurities about Paige’s relationship with Max. Shane encouraged his son to talk to Paige about whatever it is he is feeling but he needs to be open about it. Jacob told Paige that he was trying to be supportive; she thanked him and they continued their union together, despite their families not being happy with it. Cassie, however, continued to try to seduce Jacob but he rejected her advances. Jacob, then, proposed to Paige and she happily accepted. Max learned and told Cassie about the engagement and she realized that she had to do something to split up the couple. She invited Jacob over to her apartment, drugged him and they slept together. In the morning, Jacob couldn’t remember anything that happened. He and Paige moved forward with their wedding plans and he suggested that they eloped since their families were against their marriage plans. Jacob suggested that they go to Banff, Canada, to get married. Paige agreed. Cassie learned that they were heading there and followed them. Cassie pulled a gun on the couple just as Jacob remembered that he and Cassie slept together. Paige was horrified that Cassie drugged Jacob; when Jacob refused to reunite with Cassie, she vowed to kill them. Cassie tied them up in the garage and left a car running hoping that the carbon monoxide poisoning would kill them. Max, Jeff and Shane saved the couple and they were given a clean bill of health. Cassie, however, was presumed dead. Upon returning to Twin Peaks, Natasha threw them a welcome home party where Jacob and Paige’s families finally agreed to support their relationship. Max crashed the party and lashed out at everyone for celebrating while his mother was dead.
Jacob and Paige were stunned when Max quit his position at Robertson Enterprises. They questioned him about how he was going to be able to survive and he admitted that he inherited money from Cassie's death but he refused to work at Robertson Enterprises anymore when they were insensitive about his mother's passing. Jacob and Paige revealed this to the Calimo's; Natasha wondered if Max inherited the money that Cassie stole from Roboto and Robertson Enterprises. Everyone was stunned when Simona's investigation proved that Max inherited funds from a legitimate source, unaware Cassie pre-planned her cover up. Paige told Jacob that they had to support Max since he saved their lives but Jacob still thought Max was up to no good. They continued to squabble about Max. Jacob, then was horrified when Natasha announced she was sleeping with Tyler. Jacob accused his mother of being a hypocrite since she didn't support him and Paige at first. They soon made amends, however, but he was further stunned by Natasha's behavior at Kim and Robbie's wedding. Paige and Jacob, meanwhile, continued to bicker over Max as they learned he was planning to open his own photography studio and Jacob still believed that his inheritance was stolen from the companies. Paige, however, believed Max and the two continued to fight about it. Eventually, Paige ended their engagement because she didn't want to move into a marriage while they were fighting so much. Jacob was crushed. He was then livid when he realized Max had asked Paige out on a date. Jacob witnessed them kissing and realized he had to prove to Paige that he was right about Max. Jacob broke into Max's apartment and found his burner phone that he was using to communicate to Cassie! Jacob was floored that Cassie was alive and well. He told Natasha what he found, who wanted to call the police. Shortly after, Jacob realized that Paige and Max made love and he told Paige about what he found. Paige was in disbelief that she fell back into bed with Max, who was lying to her again.
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