Assholf 

A person found wanting in desirable social skills such as common courtesy, politeness, and due consideration of others.

Unlike an Asshole, the word Assholf is found exclusively in reference to people and totally uncalled for acts of insensitivity - esp. to individuals and/or the things they create.

May be associated with pretentiousness and transparency

I can't believe I found William in bed with Megan! He is such an ASSHOLF!

or

He said my music was minimalistic and he wouldn't add me on GaySpace...what an ASSHOLF!

Assholf by Will-yum-yum March 18, 2008

He meets assholes everywhere he goes. 

He meets assholes everywhere he goes. — An insult that points to a person who is the personification of the old southern proverb:

“If you meet an asshole in the morning; you just met an asshole! But if you meet assholes everywhere that you go THEN YOU’RE THE ASSHOLE.”

With that statement as axiomatic, by saying “He meets assholes everywhere he goes”, you are using the statement as a verbal deictic and calling the person observed an asshole.

Using “ He meets assholes everywhere he goes” in a sentence:

What a jerk! I’ll bet you that he meets assholes everywhere he goes.

It’s a very direct / indirect insult verging on shade.

He meets assholes everywhere he goes. by Mind Hunter the Profiler February 25, 2023

Ripped him a second asshole 

This is not solely applicable to blokes, females can also get a second asshole, so feminists eat your fucking hearts out. The phrase originated in the UK where it was usually “ripped him a second arsehole” but over time the spelling changed. The original meaning was to attack someone, usually unexpectedly, brutally and viciously so that they were completely overwhelmed and unable to defend themselves. It can also mean to criticise someone’s thoughts, ideas or lifestyle either with or without cause or justification. The usually accepted definition is that which is applied to the workplace where it means to reprimand someone so totally and effectively, that the person on th receiving end wishes they could crawl under the carpet and die. So if you have ripped him/her a second asshole you have delivered a rebuke of epic proportions.

That WOFS Malcolm has fucked up once too often so the boss called him in and ripped him a second asshole. He practically crawled out afterwards looking like he’d pissed himself and cleared his desk.

Ripped him a second asshole by AKACroatalin December 6, 2016

Reverse Thornton Asshole Dickfuck 

The sexual act of acquiring an erect penis, and falling face-first, so that ones penis bursts out of the anus. The female then proceeds to straddle the now raw penis.

"Yo Chev, I just saw someone doing the reverse Thornton asshole dickfuck"

"Damn, he alright?"

Reverse Thornton Asshole Dickfuck by Jerome Momas December 24, 2013

assholeitis 

A disease in which a teenager regresses in a fit of narcissism, self-centeredness, and egocentrism, refusing to be accountable to own behavior, projecting anger, rage, and immaturity throughout the world, with a sprinkling of ass-holeishness.

A person with assholeitis may display: Screaming in parents' face, in a high pitched, screeching, nonsensical grandiose way, in an attempt to be re-breastfed. A person with assholeitis will also display pervasive denial. (Seek attention from perturbed, tired, teenage peers.)

assholeitis by RESCU May 13, 2009

Mike Pompous Asshole 

An already widely popular nickname for the Trumpster’s third Secretary of State, Mike Pompeo.

Well that’s a big surprise, Mike Pompous Asshole is a proud member of the Impeachment Posse for the role he’s played in the recent intercontinental extortion attempt!

Mike Pompous Asshole by Dr Bunnygirl September 30, 2019

Shy/Asshole Confusion 

Coined by Larry David in the "The Acupuncturist" episode of HBO's "Curb Your Enthusiasm", Shy/Asshole Confusion is when one mistakes a shy person's quiet demeanor for that of an asshole.

Larry: I don't know why you call him an asshole. He's not an asshole, he's just shy.

Cheryl: No, he's not shy. He thinks he's smarter than everbody else and he sits there and he judges and he-

Larry: No, he doesn't, he's just shy! You've got shy/asshole confusion, my friend.

Shy/Asshole Confusion by Meeyort Snurn May 22, 2008