Although Jason has had many romances, all of them were short-lived since he has a fear of commitment. He has had many flings with street residents, Candice Stowe (Nikki Sanderson) and Sarah-Louise Platt (Tina O'Brien). He seemed to have settled down with Violet Wilson (Jenny Platt), even uncharacteristically promising to care for her when he thought she was pregnant. Jason is stunned to learn about Violet sharing a drunken kiss with his friend/employer, Charlie Stubbs (Bill Ward). He attempts to continue the relationship but is unable to forgive Violet and ends their relationship. During their separation, he starts dating Sarah and despite reconciling with Violet, he continues his affair with her. Eventually, Violet discovers the affair and dumps Jason. Separated from Violet again, Jason and Sarah continue their relationship, much to the dismay of their mothers. Their relationship struggles initially as Sarah feels insecure about his feelings for Violet and the fact he proposed to Sarah while still with Violet, leading to a showdown in which Sarah ends her relationship with Jason in the Rovers. After days of constant quarrels, Jason ultimately decides to get back with Sarah and after she refuses to speak to him, Jason breaks into her house and proposes. She accepts, although they suffer further disapproval from their mothers. They announce their engagement in the Rovers in Violet's presence, which Sarah wants to do to make a point. The wedding, though, is a disaster. Jason develops cold feet and flees through a toilet window at the venue, leaving Sarah heartbroken. After months of ignoring Jason, Sarah reunites with him. However, on Christmas Day 2006, Jason has a major surprise delivered to the front door in the shape of a baby - supposedly his little girl by a young woman called Emma (Stephanie Waring). It later turns out that baby Holly is the baby of Charlie Stubbs.