When Darren arranged a poker game with Warren Fox (Jamie Lomas) in the loft, Jessica came with him. The stakes got very high and Darren offered Warren his half of The Dog in The Pond - he promptly lost it to Warren. A couple of days later whilst walking through the village, Darren and Jessica followed a drunk Louise Summers (Roxanne McKee) home, so Darren can confront Warren. They walk in to find Louise passed out on the bed. Jessica and Darren see Evissa's takings on the bedside table and decide to steal the money. The following day, Jessica and Darren went to the casino with Evissa's takings and won £200,000. Jessica asked Darren what they would spend their money on, and Darren revealed that he was going use the money to buy The Dog in The Pond back from Warren. He also revealed that he planned to get back together with Zoe, much to the shock of Jessica. On New Year's Eve, Darren and Warren had a showdown and when Warren asked for the money on the stroke of midnight, Darren was shocked to discover that all of his money was gone. As Darren frantically searched for the money, Jessica departed Hollyoaks village for good - £200,000 richer.