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psychological dickhead 

Someone who makes a situation unnecessarily stressful or inconvenient in a manner that benefits nobody. Often includes usage of emotionally manipulative tactics such as gaslighting, moving the goalposts, and guilt-tripping.
P1: "If you don't buy this off me I'll burn it all."
P2: "What is the point of doing that? Just give it to me."
P1: "Nope, $600, take it or leave it."
P2: "Oh my god, you're such a psychological dickhead."

Dickhead Mission 

James ride to the store for me on your bike

No its raining outside, you ain't about to send me on no dickhead mission
Dickhead Mission by shawba August 19, 2009

Total Dickhead Event

Total Dickhead Event: a public drunken stupor so embarrassing, humiliating, and utterly mortifying as to convince the most hardend boozer to giving up the drink.
“I’ve been on the wagon since my Total Dickhead Event at Meghan and Harry’s wedding.”
Total Dickhead Event by Superchuck September 6, 2018

Backdoor, Dickhead

Philly slang for "Please open the Backdoor of the bus, bus driver". often used by teenagers and impatient adults when getting off of the bus

Philly Septa
Teenage Passenger: BACKDOOR, DICKHEAD!!!
Bus Driver: alright. here you go

Boo dickhead 

Used to make fun of someone’s misfortune or a dumb action. Typically used in a sarcastic tone.
“Bro I accidentally dropped my phone in the toilet”
“Boo dickhead!”
Boo dickhead by Not tf u January 5, 2019

Dickhead 

a person who is an idiot and shows it all too well
"Stop humping the chair! You're such a dickhead!"
Dickhead by corianna March 14, 2003