2 definitions by Robert McCall

1
Term to describe the purchasing of an expensive item, of excellent quality. Implies that the owner will, initially, have reservations or guilt for buying such an expensive item; however, the owner soon realizes they will only have to purchase the item once. Owing to its craftsmanship and durability, the item will have a long lifespan.
Bob: "Dude, this iPhone case cost me $200! It's made from Italian leather and handcrafted in Eastern Europe, though..."

Frank: "Ouch... Buy once cry once, amiright?
by Robert McCall September 25, 2015
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2
Refers to young, college-age adult women; implies they have had few sexual partners, at such a young age. Also refers to an impending expiry date, usually around 30, when they become used up party girls.
Son: "Dad, I am going to do so many chicks in college!"
Father: "Boy, go get 'em while they're young and fresh!"
by Robert McCall January 17, 2015
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