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When Paul ordered Dylan to start following Izzy Hoyland, who appeared to have worked out all of Pauls schemes, Dylan happily obliged, parking himself outside of her business, the Scarlet Bar.
However, he made a mess of things on the first night when he got distracted by Sky Mangel, a neighbour who he had a serious crush on.
Later that day, he turned up on Susans doorstep and explained who he was, before impressing her and Scotts girlfriend, Serena Bishop, as he told them of his plans.
However, when Scott, or Stingray as he had become known, returned home, he didnt stop to listen to any explanations and punched his brother in the mouth.
Dylan went out of his way to please his mum, but she only had time for her Scotty, the success story of the two brothers, even admitting that Dylan only reminded her of her loser husband, Kim.
Realising that he had the chance to impress Janelle on her birthday, Dylan went out and bought her a ring, but once again, the gesture got thrown back in his face and he returned to living at number 28.
Dylan accepted this, admitting that hed often used his younger brother as a punching bag when they were growing up, but Susan managed to convince Stingray to put the past behind him and give his brother another chance.
Dylan comforted her and they ended up sharing a kiss, at which point a confused Sky ran off and Dylan realised that hed completely missed Izzy leaving the bar.
The following morning, Dylan parked himself outside the flat which Izzy had shared with Karl Kennedy and where the pair of them had retreated to.