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A West Los Angeles private school at which students are often smart & rich. Unfortunately for other local schools like Archer, Harvard Westlake, Brentwood, Crossroads, and, Oakwood, Students at Windward tend to be better than everyone at nearly everything. A typical "Windward boy" will have 6pack abs, be somewhat metrosexual, and, be incredibly friendly. A "Windward girl" is usually nice, but, can most likely be found with a blackberry in one hand and a Starbucks in the other.
Girl 1: Hey do you go to Windward?

Girl 2: No, why?

Girl 1: Nothing, i thought i recognized you from Starbucks

Windward Boy 1: Hey Bro, after school, wanna go on a run around the park so we can take off our shirts and "accidentally" show our abs to the group of girls by the locker room?

Windward Boy 2: Defiantly, let me just go put my cardigan in my locker and do a few more good deeds.
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An elite Los Angeles School wherein you will find extremely intelligent individuals who reign supreme in pretty much everything they do. However, they tend to be quite snobby due to their extreme wealth.
Hey you know him?
Yeah he went to windward.
Oh, now wonder he's going to Harvard with his Ferrari.
Windward by 6uf42 September 9, 2010
A school that doesnt care about its students.
Windward is horrible for students.
Windward by zykovitz December 10, 2021

Windward port

When you open the sheets and allow air in or out after a fart to either avoid or clear a dutch oven. specifically applying to when others are in the bed with you.
i was trying to be nice to her and opened a windward port so as to not offend
Windward port by Liondcat April 8, 2015

Admiral of the Windward Passage

Every time I wore those pants, I'd get some Admiral of the Windward Passage trying to make eye-contact.

Navigate the Windward Passage 

Captain Cook couldn't wait to show the Tahitian Cheif's daughter how well he could Navigate the Windward Passage, before a Ziffon and setting sail for Australia.

navigator of the windward passage 

A homosexualmale
the guy is a navigator of the windward passage
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