He is interested in Charlotte "Big Jugs" Hinchcliffe, and the two of them have been known to spend time together, with Will accidentally ruining their relationship.
He nearly lost his virginity to Charlotte after telling her in school a few days prior 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".
Carli agreed to meet Simon at the local pub for a post-exam drink, but when she arrived it was revealed she had reconciled with her boyfriend, to the disappointment of Simon.
Will serves as the narrator in the show and is therefore the principal character. He becomes best friends with Will after initially avoiding him due to his "actual briefcase", "clumpy shoes" and "gay hair".Simon has had a crush on his childhood friend Carli D'Amato since she was eight years old, an interest which becomes more apparent throughout the series.Despite many pathetic attempts to show her his feelings – such as spray painting "I Love Carli D'Amato" on her driveway – for a long time she didn't reciprocate, partly due to having a boyfriend, but in the final episode of the second series: "Exam Time", Carli seemed interested in Simon after she split up with her boyfriend Tom, and they end up kissing while revising for A-levels at Simon's house.Will aspires to have a career in law or maybe the media, and was supposed to be attending a local newspaper office for work experience.However, a mix-up with applications sends Neil to the newspaper office (instead of "driving aeroplanes") and Will spends his placement at a garage, where he ultimately fails to fit in and gets bullied by the staff working there.Will later attempts to arrange a final camping holiday with the lads before they go their separate ways after leaving school.Will is the only character out of the four to never pass his driving test; this is in large part due to the fact his mother did not sign him up for driving lessons on his 17th birthday as she thought the minimum age was 18.They unexpectedly share a kiss when Kerry escorts him back home, which gives her the impression that they are now dating.At Neil's eighteenth birthday party, Will causes outrage by attempting to harshly break-up with Kerry, not knowing that her father had died a month previously, and that Tara had arranged their relationship to comfort her.Simon's first task of the new term is showing Will to his classes – a task assigned by the Head of Sixth Form, Mr. Simon being the eldest; was also the first to learn how to drive, having passed his driving test (in dubious circumstances) before Christmas.His father bought him an old small, yellow Fiat Cinquecento Hawaii – Simon, his friends and others think the car is very embarrassing and dislike the colour, and mock the fact that it has a tape deck.