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Will and Gypsy's relationship is frequently tested, such as both being grilled after they were locked in the school overnight after sneaking away at a concert.
They fall out after Will is dismissive after their first attempt of intimacy.
When Irene leaves to visit her daughter Finlay (Tina Thomsen), Will, Hayley and Joey stay with Ailsa Stewart (Judy Nunn).Gypsy becomes jealous when she sees him hanging around with a new girl.The girl is revealed to be his sister Hayley who left her foster parents and decided to come and live with him.Their relationship suffers its first test when Tara Mills becomes infatuated with Will after he helps her out.Will is happy when Ken and Irene become engaged but it is not to be as Ken is killed when a jack slips under the car he is working on, leaving him crushed.
Will blames himself as he lifted the car off Ken which released the pressure, quickening his death.