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assholescent 

adj: to be both adolescent and an asshole
A British girl told me that football riots are usually started by assholescent wankers.

Assholephrenia 

What should be a clinical diagnosis for a person who has all the bravado of a Mensa member, but the substance of a meringue, and an I.Q. that rivals that of a 10 watt lightbulb. Often looks for a reason to complain, criticize, sabotage or simply act like a douchebag with no provokation.
My ex-girlfriend got mad after I cheated on her, kicked her dog, called her mom fat and stole her car.

Doctor: You have a condition known in psychiatry as Assholephrenia.
Assholephrenia by LISW April 14, 2009

assholescent 

noun: an immature, aimless, broke, unanchored person over the age of 35 who is a spendthrift parasite living off of a rotation of working friends, and who assumes no personal responsibility, despite many parental contributions,and failed college enrollments.
Lars: "Last night Dick came over and ate the rest of my pizza, drank four beers, and crashed on my couch. He asked me to lend him a $20 for gas."

You: "Dude, he's such an assholescent---toss him."
assholescent by Janwriter June 4, 2010

assholescence 

The annoying period of development between the onset of puberty to being a rationally thinking adult.
Know-It-All 12 year olds are just entering the assholescence stage of their development.
assholescence by strumpet vine March 28, 2011

Assholeson 

Descendants of colonialism; namely, British, Canadians, and Americans who had stolen the land of the indigenous people and the genocide.
Many of us did not realize we are Assholeson.
Assholeson by Seeit July 10, 2021

Assholesome 

Being an asshole but for the right reasons.
She is so assholesome. She tells me what I need to hear.