List of The Inbetweeners charactersSimon is the oldest member of the group. He becomes best friends with Will after initially avoiding him due to his "actual briefcase", "clumpy shoes" and "gay hair". Simon's first task of the new term is showing Will to his classes – a task assigned by the Head of Sixth Form, Mr Gilbert. Simon, being the eldest, is also the first to learn how to drive, having passed his driving test (in dubious circumstances) before Christmas. His father buys him an old small, yellow Fiat Cinquecento Hawaii – Simon, his friends and others think the car is inadequate and dislike the colour, and mock the fact that it has a tape deck. The car's passenger-side door is ripped off due to Jay opening the door and it colliding with a pole whilst having an argument with Simon when he was reversing at Thorpe Park. However, in "Caravan Club", the door has been replaced with a red one.
Simon has been attracted to his childhood friend Carli D'Amato since they were eight years old. Despite many awkward attempts to show her his feelings – including spray painting "I Love Carli D'Amato" on her driveway – for most of the time she does not reciprocate, partly due to having a boyfriend, Tom, but in the final episode of the second series: "Exam Time", Carli seems interested in Simon after she split up with her boyfriend Tom, and they kiss while revising for A-levels at Simon's house. Carli agrees to meet Simon at the local pub for a post-exam drink, but when she arrives it was revealed she has reconciled with Tom, to the chagrin of Simon. His parents briefly go on a trial separation in "The Duke of Edinburgh Awards", but they have reconciled by the end of the episode.
In series 3, Simon takes part in the school charity fashion show, but humiliates both himself and Carli when he walks along the catwalk wearing Speedos with a testicle sticking out. In the episode "The Gig and the Girlfriend", Simon gets a girlfriend, Tara, whom he kisses at a concert. The couple break up at the end of the episode "The Trip to Warwick" after they fail to have sex due to Simon being unable to get an erection. Simon is the most volatile of the group, especially when in discussions with his family, where he frequently over-reacts to gentle goading and even advice. He is sometimes shown to be extremely impulsive and bitter, saying and doing things that cause him great embarrassment. He also gets into a slew of unfortunate situations including being physically and verbally attacked (once by a twelve-year-old), accused of being a "paedophile" on numerous occasions, failing to have sex with his former girlfriend Tara after taking Jay's questionable sex advice, and humiliating himself in front of Carli, most notably during the fashion show. In the last episode, the boys play a game where they swap mobile phones, and have to send a text message to anyone of their choice on the phone's contact list. Simon later receives a reply from Carli that leaves him with a smile, which suggests she indicates that she feels the same way as Simon, and indicates that there is more in store for him and Carli. Provided by Wikipedia