:(

Well, since CR has been getting more and more strict, I have been unable to really get anything funny out of it. Omegle is now overrun by spam, and so I must sadly admit that I am done. I hope you enjoy the goodness that I did get, though!

UPDATE

Yes, I'm still here. I am trying to increase the quality of the output here, but given the recent legal crackdown on Omegle, and the recent closing of Chatroulette (with promises to return), it's been tough. Here's the best thing I've gotten in awhile, and I'm not proud:

You're now chatting with a random stranger. Say hi!
Official messages from Omegle will not be sent with the label 'Stranger:'. Strangers claiming to represent Omegle are lying.
Stranger: I'm seeking a forger. He might be drunk.
You: well, then he's a bad forger
You: forgery is something that should be done sober
Stranger: But he's not forging now.
You: oh ok.
You: why might he be drunk right now?
You: and what makes you think i can help?
Stranger: I don't think you can.
Your conversational partner has disconnected.

So, there is a future... maybe.

I just discovered Cleverbot.

www.cleverbot.com

This is a website with some of the best AI I've ever seen. I realize this goes against my usual chats with real strangers, but I figured it was close enough. Obviously you can trick it with absurdity, but I wanted to see just how advanced it was. So I kept on talking with more complicated language as I went. As you can see, though, it has a limit.

User: Yo.

Cleverbot: Yo yo.

User: What's on your mind?

Cleverbot: You.

User: But, you don't even know me.

Cleverbot: But we're married.

User: Since when?

Cleverbot: Since yesterday.

User: I was at home yesterday.

Cleverbot: I was at your house this is the same person that was talking ot you about names.

User: No one talked to me about names.

Cleverbot: Tell me about yourself.

User: You should know. You're my wife.

Cleverbot: I am not god.

User: I know that.

Cleverbot: I do not.

User: But you just said it.

Cleverbot: Yes, but it was a joke.

User: Oh, I get it. You're funny then.

Cleverbot: Are you God?

User: Nope.

Cleverbot: Who are you then?

User: Just a bored boy.

Cleverbot: Oh, so you're a female?

User: That isn't really funny.

Cleverbot: Just a small town girl.

User: Yes, living in a lonely world.

Cleverbot: She took the midnight train going anywhere.

User: I don't like Journey very much.

Cleverbot: Why?

User: I can't explain that. It's an aesthetic thing. Art doesn't have concrete reasons.

Cleverbot: Everything has a reason.

User: What is the reason for the human coccyx?

Cleverbot: I wear the black for the poor and the beaten down.

Poor girl.

You're now chatting with a random stranger. Say hi!
Stranger: hey there
You: man, i need to see some funny shit
Stranger: do u think will be funny see my boobs ?
You: i think people with horrible grammar are funny, in a pathetic kind of way
Stranger: nice
Stranger: :)
Your conversational partner has disconnected.

This seems cooler than it is, but I don't care.

Weekends are so advanced, they encompass the entire week.

Might have been guess, but I don't care.

You're now chatting with a random stranger. Say hi!
You: tupac or biggie?
Stranger: wat
You: pick one
Stranger: biggie
You: correct
You have disconnected.

Uncreative dude. Didn't expect me to be serious.

You're now chatting with a random stranger. Say hi!
You: hello
Stranger: my dog ate one of my testicles...
Stranger: what do I do?!
You: really? how recent?
Stranger: like six years ago
You: well... have you received medical treatment and stuff?
You: i mean, you are all healed and no infection and all that?
Stranger: no! i've been hot glueing oranges there and pretending I'm normal.
You: welll...
You: if your other nut is the size of an orange, i think it takes care of the problem. an orange-sized nut is equal to two normal nuts
Stranger: I have STDs
You: oh really? well, i don't see how that relates. probably from all the activities that require dogs to be near your junk.
Your conversational partner has disconnected.

I did!

This is how I look every morning, actually.

Did Frankenstein and MF Doom have a kid?

Honesty.

You're now chatting with a random stranger. Say hi!
Stranger: are you a horny girl 18 or over?
You: i am the precise and fine-tuned opposite of that
Your conversational partner has disconnected.

This person fails at funny.

You're now chatting with a random stranger. Say hi!
Stranger: i like frogs
You: me too!
You: they are so damn cute
Stranger: HOW DARE YOU, I HATE FROGS, THEY KILLED MY PARENTS............
You: you seem... indecisive
You: but i still like them
You: was that all the crazy you had? you need to work on extending this joke.
You: this silence is weak.
Stranger: FROG U!!!!!!!!!!!!!!!!!!!!!
Your conversational partner has disconnected.

What a champ.

You're now chatting with a random stranger. Say hi!
Stranger: 找啊找啊找朋友 找到一个好朋友 敬个礼呀握握手 你是我的好朋友
Stranger: hi
You: OH FUCK
Stranger: fuck 有
Your conversational partner has disconnected.

I met my wife today in crazyville.

You're now chatting with a random stranger. Say hi!
You: hello love
Stranger: hiyeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeerrrrrrrrrrrrrrrrrrrrr
You: WELL JEEPERS
You: CREEPERS
Stranger: my lover?? YOUR BACK?
Stranger: from outer space
You: of course!
You: i was on neptune!
You: WITH A HORSE
You: A HORSE KING
You: OF NEPTUNE
Stranger: :O what were you doing then precious???
Stranger: you best not have been cheating on me.
You: i am a neptune knight now
You: nope, just out on a space crusade
You: i could never cheat on you, my sugar muffin pie
Stranger: phew. you should of brought me along dear.
You: sorry
You: i didn't want you to be in space-danger
You: from the space-lions
Stranger: i thought you killed them when you went there last?
You: no no no
You: those were space-tigers
You: they look similar
Stranger: ohhhh. well my husband, i understand. im glad we finally get to talk again (L)
where are you now my cream pie of love?
You: i am in my wifi-capable space ship, coming home to our fun little house to make sweet sweet spaceman love to you, my mushy gushy gumdrop honey pie wifey boo
Stranger: oh god.
Stranger: honey, a space-rhino just walked into our living room.
You: WHAAAAA
Stranger: RUN!
You: wait, our earth room?
You: THAT"S CRAZY
You: get the space rhino tranq!
You: hurrrrryyyy
Stranger: oh yes! i always forgot we keep one of them under the couch!
Stranger: i zapped him honey! we're safe! :)
You: we also have space rhino insurance
You: YAY
You: i'm glad my lovey-pops is safe
You: and how is little arthur h. mcflannaginheim sleeping? like a baby?
Stranger: oh yes, you'd be so proud of him! he has a young girl up there with him :)
Stranger: even though hes 3, i think hes making love.
You: OOOOOOOOO wow. our son is a little stud.
You: of course
Stranger: we brought them up in a good way.
You: with our strong genes, its natural that he'd be baggin space-ladies left and right at his age
Stranger: im so proud of him :)
You: so, how was your day, puddin popz?
Stranger: its been great, been missing you lots though my cream pie :(
You: awwwwwwwwwwwwwwww.
Stranger: do you know when you'll be home?
You: hopefully NOW
You: oh crap
You: well then maybe in a few hours
You: the commute is rough today
You: asteriods and stuff
You: *asteroids
Stranger: oh, dont worry dear. you fight those asteroids and save me and our little Arthur for when the Earth is safe.
You: awww you're such a good space-wife. i'm so lucky.
Stranger: im so lucky to have such a great space-husband who loves me so much :D thankyou space husband! i will be going now, im glad we had this talk. ill see you very soon my beautiful cream pie!
You: yay!
You: bye bye my muffin lovey pile
Your conversational partner has disconnected.

I was disappointed!

You're now chatting with a random stranger. Say hi!
Stranger: men älskling vi ska alla en gång dö
You: hello
You: HOLY SHIT
You: ICELAND
Stranger: hahaha no sweden
Stranger: were are u from
You: oh well that sucks
You have disconnected.

That's what you get for insinuating that I am stupid.

You're now chatting with a random stranger. Say hi!
Stranger: what do you want?
You: yo
You: i want some foooood
Stranger: haha
Stranger: me to!
You: word
Stranger: american?
You: yepper
Stranger: thought so.
You: why is that? the food?
Stranger: no..'word'
Stranger: :P
You: haa
You: yep
Stranger: such an americal word to say
Stranger: *american
You: that it is
You: well, i'm colloquial on here
You: we use more non-formative idiom
Stranger: whats colloquial?
You: yeah fuck you
You have disconnected.

There has been a distinct shortage of funny lately. I blame this champ.

You're now chatting with a random stranger. Say hi!
You: please god say something funny.
You: i;m desperate
You: *i'm
Stranger: POUR SOME SUGAR ON ME!!
You: WHY DOES EVERYONE SUCK AT THIS GAME????
You have disconnected.

I hope this is true.

You're now chatting with a random stranger. Say hi!
You: hey
Stranger: hi
Stranger: asl
You: 22, m, usa. got anything crazy to say?
Stranger: im in love with my boyfriends exgirlfriend.
Your conversational partner has disconnected.

This was not the desired result of this experiment, but it worked out pretty well.

You're now chatting with a random stranger. Say hi!
You: sun ra
Stranger: hornyyy
You: well, we are into different things, then.
Your conversational partner has disconnected.