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1.
"Dick Roll" is derived from the worldwide internet prank known as the "Rick Roll" where a video would be posted claiming to be something interesting when it is actually the music video "Never Gonna Give You Up" by Rick Astley. A "Dick Roll" describes the situation in which a someone highly suggests a friend or acquantaince of the opposite sex for you to date, only to realize that the said person is hilariously unattractive. Such a situation occurs often either as a cruel joke, or as an attempt to complete a double or group date.
1. Guy A- "Dude, I have this hot new neighbor across the street who's single and looking, you should take her to a movie sometime."
Guy B- "Hell Yea!"
...Later...
Guy B- "You asshole that bitch was ugly as hell"
Guy A- "YOU GOT DICK ROLL'D"

2. Girl- "Hey! my roomate really wants to get to know you she's seen you on campus a few times. She's really really sweet and beautiful too! I KNOW! We should all go to that concert coming up that my boyfriend's taking me to! Oh my god that'll be so fun!"
Guy- "Cool"
...Later...
Girl- "Soooooo player how did you like my roomate? (hee hee)"
Guy- You totally Dick Rolled me.
by Aaronius8 August 23, 2009
30 9
 
2.
A variation on the rickroll. Someone posts a bogus link that is purported to be for something interesting, funny, or hot, like lesbians making out. The unsuspecting victim clicks the link, only to see a picture of a penis and/or naked man. Usually the victim is a straight guy, and this of course is not something he wants to see.
Joe was expecting to see some hot lesbian porn, but instead he got dickrolled.
by Puffaluffagus April 20, 2008
25 8
 
3.
When one is on Chatroulette and is unwillingly exposed to someone's dick. This is a variation of the rickroll, albeit a much more disgusting one.

For one who exposes their dick on Chatroulette, see dickroller
Aw, dude, I was on Chatroulette and I got dickrolled!
by gods-shoes April 09, 2010
4 1
 
4.
Simmilar in many ways to a Rick Roll, simply because you are sending a picture of your junk to somebody you either love or hate, disguised as something that would interest them.

See Also. Trojan Balls.
1. Hey man, i totally wore this chick out last name, wanna see her tits?

2. Sure, Im totally a virgin

1. Your going to love it.

2. Ughhh, it's you cock. i can't beleive you Dick Rolled me AGAIN
by CheddaTheHulsta! April 08, 2010
8 5
 
5.
A total idiot acting like a normal person for a brief period of time.
My boss can't to anything correctly on most days, but today he's on a dickroll and really taking care of business.
by BigBossMan99 February 10, 2014
1 0
 
6.
When you're just about to have sex, and your woman is waiting in anticipation for your pulsing manhood, you turn on your music player and blast Rick Astley's "Never Gonna Give You Up", rick rolling them.
Girl: Oh baby, I want you so badly, give it to m-
Speakers: WE'RE NO STRANGERS TO LOVE! YOU KNOW THE RULES, AND SO DO I!
Girl: Wtf?
Guy: Dick Roll'd, bitch!
by Ronix April 20, 2008
18 17
 
7.
When you go from a hot chick to a penis in chatroulette.
"Damn it! She said she was going to show me her boobs, but then I got Dickrolled".
by Almoney50 September 05, 2010
1 1