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He nearly lost his virginity to Charlotte after telling her in school a few days before that he had had numerous lovers, although when they did attempt to have sex, Charlotte was let down by Will's unsuccessful attempt; in his own words "rubbing up against the perineum".In series 3, Will is convinced into going on a double date with Simon, Tara, and Tara's friend, Kerry (or "Big" Kerry according to Will).
He is seen to be interested in Charlotte "Big Jugs" Hinchcliffe, and the two of them have been known to spend time together, with Will usually accidentally ruining their relationship.Will also appears to follow certain ethical laws, though is not above occasionally committing dubious acts, such as purchasing alcohol illegally, insulting Neil's father while intoxicated, accidentally insulting people who are disabled, among others.Will aspires to have a career in law or maybe the media, and was supposed to be attending a local newspaper for work experience.He is generally sophisticated, sensible and possesses intelligence that surpasses that of his friends.Another dominant characteristic is his tendency to deliver sarcastic, dry humorous remarks, some of which get him into trouble.Will moves from a public school to a local sixth form comprehensive school because his mother, Polly, can no longer afford the private school fees.
On moving to the new school, Simon, Neil and Jay reluctantly become Will's friends after initially trying to avoid him.
At Neil's birthday party, Will causes outrage by attempting to harshly break-up with Kerry, not knowing that her father had died a month before and that Tara had arranged their relationship to comfort her.
Will later attempts to arrange a final camp-out with the gang before they split up after leaving school.
Angela Yee: How many people would you say you’ve been in love with?
Angela: I’m just saying, I’m assuming those were the two people you were in love with.
The group warm to him after several efforts to win their friendship – including successfully buying alcohol and almost having sex with the school's most attractive girl.