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yard sailing 

A phrase used to describe the art of shopping at large numbers of yard sales, garage sales, and estate sales.
"I can't WAIT to go yard sailing this weekend!"

"Yard sailing is my favorite activity of late."

"There's nothing I would rather do than go yard sailing."

sailing with the captain

To drink large quantities of Captain Morgan's Rum, usually with a group, and hopefully to the point of oblivion.
That girl I hooked up with was so fugly that I had to go sailing with the captain before I could bang her.
sailing with the captain by Robb December 24, 2003

Sky Sailing

Sky Sailing is Adam Young's OLD Pre-Owl City project. It consists of mainly laid-back and acoustic songs. It has recently been released to the public. Any Adam Young / Owl City fans should check this out!
Sky Sailing uses NO AUTO-TUNE! It doesn't sound like Owl City. It's much more beautiful.

Me: Oh, I love Adam Young's project, Sky Sailing. Its so relaxing.

Friend: Oh, I prefer his project, Owl City. The auto-tune makes him sound nice.

Friend 2: I think he sounds PERFECT either way!
Sky Sailing by Smile4Music June 21, 2011

College Sailing 

The only sport on campus where you can compete and travel with members of the opposite sex. Must be adept at hiking out (hooking your feet under straps while hanging your butt over the edge of the boat) in all weather conditions and leaning in (to the bar) after the regattas. Typically a good sport for engineers who like the physics of how boats work and business majors who enjoy the sport's social side. College sailors will learn fun new vocabulary words like croakie, burgee, halyard and roll tack. Many students join college sailing teams for the cool swag.
I joined college sailing so I can travel to regattas, meet preppy guys and party at the yacht club.
College Sailing by Sailing Ace September 6, 2013
sailing: (v.) to manhandle the wind as to propel a sailboat on the very edge of catastrophe. see also: insanity, beastlyness, and epic.
Dude, you wanna go sailing today? It's blowing 35 knots

Did you expect me to say anything other than YES?
Sailing by MajorSailor December 21, 2009

Sailing the Red Sea 

Shagging a girl that has her period.
Having sex with a girl that's menstruating.
Sailing the Red Sea by Dutchgit December 16, 2003
More from Urban Dictionary
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

Surf Dracula Syndrome 

A phenomenon in film/television series, most notably streaming series, where the main premise is drawn out to such a point that it takes an entire season or more to get the parts of the series the audience is actually interested in seeing.

For example, if a series is titled "Surf Dracula," a majority of viewers would tune in expecting to see Dracula surfing by the first or second episode. However, the entire first season would instead be tedious padding and backstory before finally ending with Dracula surfing in the last five minutes of the season finale.
I watched "Smallville" on Netflix the other day. Dude, it was ten seasons of filler before he finally flew! Major Surf Dracula Syndrome!
Word of the Day on October 24, 2026

Northstarring

Finding your way back to the truth by fixing on one verified fact and working out from there, the way you navigate by the North Star when everything around you is spinning.
Rumours were flying everywhere, so she went northstarring — one checked fact at a time.
Northstarring by Light Bearer October 22, 2026
Word of the Day on October 23, 2026

Plate of Brown 

A plate of brown consists of foods that have little to no nutritional value, and are typically deep fried. A true plate of brown will also be accompanied by a dark soda.
Wanna go to meal hall & grab a plate of brown?
Plate of Brown by Cheddar Craigson September 18, 2020
Word of the Day on October 22, 2026

Larpenomics

When finance content creators rent out fancy cars and flex cash to seem richer than they really are in order to promote and sell their “get rich quick” courses.
Andrew Tate has mastered the field of larpenomics
Larpenomics by Rbois09 October 21, 2026
Word of the Day on October 21, 2026
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