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14.
1. Basically it's a site where you go on a web cam and are hooked up with another random person on a web cam and every time you click next or your partner clicks next you disconnect and are connected with another random person. About 90 percent guys.

2. A site that can completely destroy someone's self esteem, much more so than high school. Full of assholes.

3. A site where everyone likes to joke about how you sometimes come across a guy masterbating.. Because it's so hilarious the tenth time you've heard it.
1. "Man there are so many guys on that chat roulette, you know the site where you get to see and talk to random people."

2. Random girl on chat roulette: I like your eyebrows, they turn me on ;)
*clicks next and joins the club with the other 20 girls.*
Random fat woman on chat roulette: *starts laughing*
*clicks next*
*person dies a little inside*

2. Mike never thought he was that ugly, every now and then it would seem like a girl had a crush on him, or was checking him out, or he would hear about people complimenting him on his looks in some way or another. This perception completely changed when he went on chat roulette and at least 80 percent of the people on there (particularly the attractive girls) either laughed at him and clicked next, made fun of me then clicked next.. I mean.. him, or simply clicked next.

3." lol there's no point to chat roulette it's totally full of penises."

"zomg you're so hilarious, what a witty observation. No one's ever said that before.
by UltimateToast September 17, 2010
 
1.
A live streaming website where you connect with completely random strangers with a webcam and microphone. Every other person you connect to is a horny dude wanking, or if you're a chick, you are asked to see your tits. You disconnect with you want and keep talking if the person's chill. Same concept as Omegle except you see them.
Dude, I just saw someone take a shit on chatroulette.
by jerseyshore January 17, 2010
 
2.
A brilliant invention. A place where all the psychos, skanks, perverts and pedophiles are kept the world over, safe in their living rooms, instead of out bothering the rest of us in the real world.
Guy1: My uncle is such a pervert.

Guy2: Did you introduce him to Chatroulette? =D

Guy1: Say, that's a swell idea!
by JaneGirl3345 March 10, 2010
 
3.
Another weird novelty of the internet, consisting of randomly chosen webcam(if permitting) chat sessions at www.chatroulette.com This is often extremely deviant, and often consists of bored males, with the odd one flopping their cock out or worse.
<dude 1> hey bro have you been on chat roulette?
<dude 2> hell yeah man the first time I went on there I saw 3 different dudes cocks
by kasabian are well massive December 24, 2009
 
4.
A website that has video chat between two people that contain almost no hot chicks.
Population distribution as follows:
34% wankers
25% creepy pedophiles
13% emo kids
12% douchebags
6% wannabe gangsters
2% normal guys
1.999% decent looking chicks
.oo1% fine chicks
I was trying to find some babes but i kept seeing guys beating their meat on chatroulette
by Kontizle March 07, 2010
 
5.
One of Earth's most ridiculous websites that randomize a video chat session with another random person in the world with a webcam. No downloads required. Anything goes.

Things to expect while on chatroulette.com
-4 out of 5 are male
-about 1 in 6 odds that male is jerking off or showing full frontal
-about 1 in 4 odds the male is looking for a set of nice titties
-a video on repeat (porn, something misleading, often ridiculous)
-that token 50+ year old
-college dudes
-less college chicks
-dudes looking to chat someone up
-girls looking for attention and compliments (see: tease)
-pre-pubescent middle school girls
-people from other continents (duh)
-a short conversation
-a long conversation
-racists, insecure people who act racist because they are behind a computer screen. (See: chatroom thug,tool,poser)
-people with ridiculous costumes
-people you wonder why the fuck the are on chat roulette
-non-sexual entertainment (rare)
-rejection
-a good laugh (LMAO, die laughing)
-and on rare occasion a girl who puts on a show

Similar websites: tokbox, omegle, etc

You never know what to expect from this site.
Guy 1: Dude, let's fucking chat roulette right now, I wanna see what some titties and/or asian girls!

Guy 2: I didn't know you were that anxious to see some dude jerkin it while sitting in his dark bedroom. But yeah I can go for some titties.

Guy 1: I have a feeling we'll see some titties from tits mcghee today.

(five clicks later)

Guy 1: Ah fuck! some dude jerkin' it...Do you think he does this all day?
by Sexual harassment Pandaa March 01, 2010
 
6.
a place to see dicks
guy1 have you been to chatroulette.com
guy2 you mean "dick"roulette.com?
by daman555 May 15, 2010
 
7.
an internet webcam/chat relay where anonymous homosexuals hang out to display and stroke their small hairy penis.
Chatroulette is plagued with faggots stroking penis.
by Lays Chips April 09, 2010