The town in which the movie Donnie Darko took place.
Other guy: Hey Donnie, what school do you go to?
Donnie: Middlesex High School
by Radomsooner March 4, 2010
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Town that is full of tough guys. They act tough to everyone and nothing scares them. They are all hardasses and don't give a damn. They are known for their whiteouts and sick chants and the roller coaster at halftime. They will put any other fans to shame asbling as the situation presents itself. This us all with the help of the loudest man alive who currently lives there.
Middlesex: If you're winning and you know it clap your hands!

by Anonymous4e March 13, 2009
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A place in England. Also the middle position during a threesome .
Jimbo: Come on man I don't want to be Middlesex again.
Carla: Sucks to sex
by FrikBoy January 19, 2022
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Bill: Was the other night good?
John: Eh, it wasn't good or bad, it was just middlesex.
by frenchdinnerparty April 12, 2007
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Middlesex is one of the top boarding schools in the US. Founded in 1901 and located in Concord, MA, Middlesex has about 350 boarding and day students. In addition to a very rigorous curriculum, the school has a great arts program and strong sports teams, especially for a smaller school. Middlesex is a member of the ISL; its rival is St. George's. Graduates go on to some of the best colleges and universities. Middlesex has some pretty famous alumni, like Steve Carrell and Bill Richardson. The school has become much more geographically diverse in recent years, and the student body now comes from all over the country and the world. The kids are really preppy, but it's still a tight-knit community where everyone works hard and knows when to kick back and relax.
The Middlesex School boys lacrosse team has won the ISL championship 7 times in 10 years.
by pudgey006 August 12, 2010
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A euphemism for lesbianism, most commonly used in the UK
the calculating creationist may consider Middlesex Cricket to be inherently evil
by internalcat May 6, 2011
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a preppy prep school in concord massachusetts where rich kids pretend they're not rich and poor kids pretend they're rich. alot of drug use and alot of joking about being gay, which 60% of the school most likely is. 90% of the school owns ralph lauren polo shirts in at least 6 colors. the person wearing the brightest colors wins "best dressed".
hey that kid's wearing a pink shirt and lime green pants and light blue shoes, and pretending to anally rape his friend, he must go to middlesex school.
by dadada1234 December 22, 2005
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