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.
by YouHadMeAtYourProperUseOfVerbs December 31, 2011
Get the Windward mug.
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.
by 6uf42 September 9, 2010
Get the Windward mug.
Every time I wore those pants, I'd get some Admiral of the Windward Passage trying to make eye-contact.
by nom de plumb June 3, 2009
Get the Admiral of the Windward Passage mug.
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.
by Cinocat December 1, 2011
Get the Navigate the Windward Passage mug.
A homosexualmale
the guy is a navigator of the windward passage
by eggydip June 11, 2004
Get the navigator of the windward passage mug.
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
by Liondcat April 8, 2015
Get the Windward port mug.
"nice-guys don't go for anal"
Chantal: I thought gentlemen never sail to windward.
Rodriguez: I'm no gentleman, baby.
by Carl Figleaf August 15, 2022
Get the gentlemen never sail to windward mug.