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When one sails a boat by himself. It can be a male or female - but it is always called mansailing. It is synonymous with singlehandling.
Damn! Look at Conner mansail that C22.
mansail by twis May 28, 2009
Related Words

manrailed 

1. The physical act of being railed by a man
2. When two men join together in the physical homo erotic act, typically with one man taking lead or "doing the railing" of the other man
I got manrailed last night
manrailed by trinn December 2, 2014
a disgusting growth on the back of your head, rejects all the ladies and smells like 400 decomposing babies in death valley.
Person 1: Omg! Whats that on your head?! EW IM NOT HAVING SEX WITH YOU ANYMORE.
Person 2: Sorry! Its just my mantail!
mantail by AsanteSwagger April 12, 2011

macfailure

Some poor soul whose last name just happens to involve a spelling very similar to 'fail', and everyone else picks up on the last syllable, and thus the person becomes a macfailure.
Person One: So, what's your last name?
Person Two: MacPhail.
Person One: As in, like, you FAIL everything? *laughs*
Person Two: *Bored* Yes, exactly like that.
Person One: You're a MACFAILURE!
Person Two: Wow, thats the first time i've heard THAT one!
macfailure by thetower April 1, 2009

Mainfail 

n. 1. A mistake which one finds comedic

2. A mistake that one desires to make light of

3. A major screw-up

note: One does not "do" a mainfail, but "hoists" a mainfail. The word originates from the play, "A Christmas Carol" in which actors have been known to yell, "Hoist the mainfail!" when the line is actually "Hoist the mainsail!"
1. AAAAAAAAhahahahahaha! I can't believe we just did that! Hahahahaha! We should know better by now! Hahahahahaha! I guess we just "hoist the mainfail!" Hahahahahaha!

2. Wow. We just made a really stupid mistake. Talk about mainfail hoisting. Now, back to business...

3. You just ran over my dog, the mainfail hoister!
Mainfail by cthretard1 April 12, 2009
A Fail paki 2Shit player named Prison Break.
He says maxfail all the time and we don't know what the fuck that means broski ?
Us: FUCK YOU PRISON BREAK L2SPEAK ENGLISH
Prison Break: SHUT THE FUCK UP U MAXFAIL.
Us:LULWUT!?
Prsion Break: *In Gay l2speak english accent*
Ey guys go watch prison break pk viddooooo 0 it it gud.
Maxfail by BubZzzzzzzzzzzz February 23, 2010
More from Urban Dictionary

kinktober 

An excuse for people to write porn with different types of kinks throughout the month of October.

Smut Fanfiction
That chick doesn't write often but when she does, its for Kinktober.
kinktober by Kinkiest July 12, 2018
Word of the Day on October 30, 2026

proper lad 

a lad that is such a lad that he is a proper lad
person1:did you see bob
person2: ya he was a proper lad
Word of the Day on October 29, 2026
The number of years you are still sexually active
While our lifespan is the number of years we will live, our healthspan is the number of healthy years we will have and our sexspan is is the number of years we will continue to be healthy enough to continue having an active sex life.
sexspan by Dr Kat April 21, 2022
Word of the Day on October 28, 2026
A lighthearted reaction upon receiving disappointing news of some sort. Usually something that isn't a particularly a big deal, esp. when it primarily affects someone else - sort of a mild schadenfreude. Sometimes doubled or tripled, and possibly said in a sing-songy voice for added comedic effect to imitate a muted trumpet, which is how the meme originated.
You didn't get any napkins with your takeout pork fried rice? Womp womp.
womp by 175623226 November 3, 2011
Word of the Day on October 27, 2026
When your wife’s boyfriend let you sleep past 8pm 😎😎
Wife’s boyfriend: You have 5 more minutes
Me: Poggers!
Poggers by Just_Charles April 14, 2020
Word of the Day on October 26, 2026

Oblication 

A vacation, feeling more like an obligation, that involves visiting or staying with family.
So Joe where are you taking the kids for spring break vacation? We are going on an oblication to Boca to visit my mother-in-law.
Oblication by kimmerr May 5, 2011
Word of the Day on October 25, 2026
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