<P> High school is a rough transition for Simon, despite help from his bubbly, popular big sister Lucy . He dates a girl named Cecilia Smith (Ashlee Simpson), and they even consider furthering their relationship sexually, but decide against it . The summer before his senior year, Simon accidentally hits and kills a boy named Paul Smith, who was Ruthie's age . Since Paul was on a bicycle with no helmet and later proven to be under the influence of drugs, the death is ruled accidental and Simon is not brought up on criminal charges . However, Simon can't stop blaming himself for the accident and also fears retaliation from Paul's older brother . He passes the CHSPE and leaves school early to start college . While in college, partly as a way to cope with his guilty feelings and low self - esteem, he breaks the family's edict of not having premarital sex . </P> <P> Simon has three serious girlfriends over the course of the show: Deena, Cecilia and Rose . Simon later gets involved with a girl that he knew from college named Sandy, who has a son named Aaron, fathered by Martin Brewer . Simon provides emotional and, at one point, maybe even physical support for Sandy and her son . </P> <P> After a scare involving his girlfriend Georgia being pregnant (it is later revealed that she only made the claim so Simon would stay with her), he meets Rose . Rose and Simon fall deeply in love, get engaged, and plan a wedding . They finally get to the wedding day, but they decide to not get married because neither is ready for marriage, and Rose still has feelings for an ex-boyfriend . Near the end of the series, Sandy and her son Aaron show up to the party after the non-wedding, and Sandy says she needs to talk to him . However, it is not revealed what Sandy wanted to tell Simon, but it is assumed that it is about Aaron's paternity; it had been hinted that Simon was in fact Aaron's father . Season 11, confirmed he is not the father . Simon eventually goes on to marry someone else or get engaged (as hinted by Ruthie in season 11), but it is unknown who, although we do find out that he graduates from college . </P> <P> Mary Elizabeth Camden (played by Jessica Biel) (born 1982) is the eldest daughter of Eric and Annie . By the time she is 14, Mary is an aspiring athlete with an immense love for basketball . As the months progress, she seems to rise in both ability and confidence (so much so that she wants to play in the WNBA someday) until she is hit by a car before the end of her freshman year, critically injuring her knee . She has a series of different boyfriends . She dates Wilson West, a guy she meets at the park while with Ruthie, who becomes her first love . He later reveals to Mary that he had sex with a sixteen - year - old girl, and got her pregnant . The girl died in childbirth, leaving Wilson with a son, Billy (actually named Wilson Jr .). By her senior year, she and her basketball teammates allow their grades to slip, which causes their coach to impose a lockout on them . After a secret meeting, the team decides to enact their frustrations by vandalizing the school gym . They are caught at the scene of the crime, and are arrested . Through a special program for first offenders, Mary is able to evade serious punishment by doing community service, which is where she meets Robbie Palmer . When she gets her driver's license, she can't parallel park but, on Lucy's advice, cries about it and the driving instructor compassionately gives her a passing grade . Mary has a dream of playing pro for the Lakers, and thinks that when her coach rings her up that this is the dream coming true, but it's actually training disabled people for the Special Olympics . </P>

Who does simon end up with on 7th heaven