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For a brief period he and Lip worked together at a Hotel, where they would steal large quantities of towels and take them back to the Gallagher household for Carol Fisher and the other Gallagher children to remove the Hotel's logo and add them to gift boxes to be sold to market vendors. He and Lip also spent a lot of their time at clubs and parties, doing large quantities of Ecstasy and Cocaine.
Lip was also dating Jack's sister, Zoe. Though they were close friends, their relationship fell apart when Jack began cheating on his girlfriend Claire with Ian Gallagher. The first time they had sex was in the Gallagher house, afterward Ian fell asleep and awoke to find Jack telling him he had to leave. Later, Debbie discovered over £100 in housekeeping money had been stolen from her room and though she blamed Sue Garland Ian began to think Jack was a lot less trustworthy than he thought.
Jack and Ian then spent some time together in Jack's car, and though Ian started to ask about the missing money he stopped himself and walked away. Soon he realized he couldn't find his keys, which had his key for the Karib's Shop attached. When Lip and Jack came to the house later that day, Ian followed Jack to the toilet and moved in for a kiss only to be angrily told that Lip was downstairs, Jack then gave Ian his keys and told him he'd left them in his car.
Later that night the Karib's Shop was entered by two masked men, they stole money, cigarettes and alcohol and then violently attacked Kash Karib. Ian and the Karib's assumed the attack was orchestrated by Kash's campaign opponent for the Chatsworth Council but when Kash mentioned that the attackers had entered the shop using keys, Ian realized what had happened. He raced to Jack's house to confront him and though Jack denied having anything to do with the robbery, Ian left angrily and attempted to reveal all to Lip.
Lip didn't believe what Ian told him, angrily telling his brother that he just couldn't stand Lip having friend's outside the Gallagher family. But during his date with Zoe at The Jockey he noticed her new phone was actually the mobile phone stolen from Kash during the robbery. Angrily asking her if her brother had given it to her he stormed over to Jack and punched him, confronting him about everything that Ian had said before leaving Jack at the mercy of the other Chatsworth residents in the pub, who weren't pleased with his treatment of the local shop's owner.
Ian's affair with Jack was also part of the end of his relationship with Kash, though Kash had met an older man and was planning to end their relationship anyway.