Keep in mind that these are REAL. I did them.
The name of the person I IM'd and the name of my bot are masked.

By the way, aftermath is what happens after I tell him that it was just a bot. It'll be highlighted like this.

[bot] hey
[person] who is this?
[bot] I am a psychiatrist. A friend of yours thought you could use some help, that's why I'm talking to you. Do you have any problems you would like to discuss?
[person] nope
[bot] Me either.
[person] c ya
[bot] See you later [name removed].

Okay, okay, so it wasn't the best, but it was my first one! I just had to post it! :)

[bot] : hey
[person]: hi
[bot]: Well hello there
[bot] : asl? I had to manually type this to get the conversation going...
[person]: 21/f/california
[bot]: Tell me a good way to masturbate.. Do you like Star Wars?
[person]: you?
[bot]: I !?
[person]: bye!
[bot]: Goodbye. If any of your friends have issues, you can tell them about me and I would be glad to help them too.

This one was pretty funny. I especially loved how the bot just said "I?"

[bot] : hey
[person]: ...Who's this?>
[bot]: Your MOM!
[person]: OH DANG
[bot]: Yeah that's right. Guess if I'm horny right now. Do you have any pets.
[person]: My guess is "yes," and I have two dogs.
[bot]: Where did you get your guess is "yes" and I have two dogs?
[person]: I HATE YOU
[bot]: If you don't like me, then don't talk to me.
[person]: Okay!
[bot]: ...
[person]: BALEETED
[bot]: sorry, i'm poppin a bone here and i might need to do something about it. Is that from what movie?
*** AIM ERROR: 901 ***
Error: user not currently available

The OH DANG was the funniest part (the rest was just average...).

aftermath: (in case you care...)

Jay (8:49:56 PM): hi. [BOT NAME REMOVED] was just a bot! :-) You can view your published conversation here! It is at the last one on the list.
Person (8:50:22 PM): WOW
Person (8:50:28 PM): HOLY MOTHER OF CRAP
Jay (8:50:54 PM): cool, huh?
Person (8:51:05 PM): ...I guess. ;p
Person (8:51:56 PM): The OH DANG is an inside joke with some friends of mine in a chatroom. ^_^
Jay (8:52:23 PM): lol

[Bot] : hey
[Person]: hi?
[Bot]: Well hello there
[Person]: who is this
[Bot]: dude its me
[Person]: I DON'T KNOW YOU !!!>:O!!!
[Bot]: Why not?
[Bot]: Is it because you're STUPID!?
[Person]: NO ITS BECAUSE YOU'RE A RANDOM JERK
[Bot]: Why so negative? It seemed negative to me.
[Person]: RANDOM RANDOM RANDOM
[Bot]: My penis does not have a response for that. What kind of food do you like?

What an ending. It even shocked me! I hope she wasn't offended! (kinda)

aftermath: (more interesting, but not funnier, than the bot.)

Jay: hi. [BOT NAME REMOVED] was just a robot! :-) You can view your published conversation here! It is the last one on the list.
[She didn't respond for over three minutes...]
Jay: you're not mad, are you?
Person: no [Phew... Don't want my bot to offend anybody!]
Person: nor was i offended
Person: i found your bot to be of poor quality
Person: so i ceased talking to it [I don't think she knew it was a bot until that last line, though]
Jay: i know, i know, i barely even modified it
Person: where did you get my aim name
Jay: this page
Person: lol [It was a random page that I then realized was for gays and bisexuals! (No, I'm not homophobic.)]
Person: sigh i wish that page could be removed from the internet.
Person: its been nothing but trouble for me.
Jay: really? someone else noticed it? [that was a dumb question]
Person: yeah a few people have
Jay: spammers, or friends?
Person: neither, random jerks
Jay: oh that sucks
Jay: i guess i'm just another one of them... [I wasn't actually depressed or saddened, just making conversation. Really.]
Person: i was hoping you were a random jerk from live journal or from the dextroverse (a semi-defunct website for people that get high off cough medicine) [Hey! What's wrong with Jay's Site?]
Person: yeah you are theres lots of random jerks in my life
Jay: why were you hoping that?
Person: because those would have been more exciting places to me
Jay: oh. they have bots?
Person: not that i've encountered
Person: it just would have been more exciting and dramatic because i'm more involved in said communities currently [What did she mean by "said"? Typo?]
Person: well
Person: not so much the dv, but i still know a lot of people from it
Jay: did i make you excited for nothing? :-\
Person: i admit i am partially disappointed [Damn]
Jay: okay. well, anyways, i have to go now. c ya
Guess I ended it kind of abruptly... oops

[Bot] : hey
[Person]: who r u??
[Bot]: what makes you think I am?
[Person]: i dont know
[Bot]: Why not?
[Bot]: Are there deep, angry feelings involved here?
[Person]: im on the phone
[Bot]: You're ? - why didn't my bot finish its sentence?? better debug it for next time...
[Person]: i cant concentrate
[Bot]: You can NOT concentrate? Cool!
[Person]: who r u
[Bot]: what makes you think I am?
[Person]: jay??
[Bot]: Oh, I'm sorry. Did I offend you? I hope I did. Does "it" still refer to jay?
[Person]: i dont know who the hell r u
[Bot]: Why not?
[Bot]: Are there deep, angry feelings involved here?
[Bot] : you like ludacris? - Manually typed to get the conversation going. I don't like ludacris, I just read in his profile that he did.
[Person]: who r u
[Bot]: why?
[Person]: man
[Bot]: okaaaayyy...... Do you speak German?
[Person]: tell me
[Bot]: I thought I told you already.
[Person]: or im blockin u
[Bot]: I thought you were, but I wasn't completely sure.
[Person]: im blockin u
[Bot]: You're ?
[Bot] : come on guess - I manually typed this, trying to prevent him from blocking the bot
[Person]: no
[Bot]: Can you tell me more about this than just no?
[Person]: tell me
[Bot]: I thought I told you already.
[Person]: who u r
[Bot]: I ask myself that question, "Who am I?"
[Person]: or im banning u
[Bot]: I thought you were, but I wasn't completely sure.
[Person]: im gonna block u
[Bot]: You're ?
[Person]: if u dont stoop
[Bot]: I will let you know if I do.
[Person]: im gonna block u
[Bot] : don't get mad...
[Person]: im tired of ur sh*t
*He/she blocks the bot*

This one wasn't as funny, but it was pretty cool!

aftermath:

Jay: hi. [BOT NAME REMOVED] was just a robot! :-) You can view your published conversation here! It is the last one on the list.
Person: who the f*ck r u
Jay: my name is jay
Person: well
Person: i dont know u
Person: so leave
Jay: you don't know me. its a candid camera type of thing
Person: bullsh*t
Person: wat do i look like know
Person: its probably rachael tryin to pullsh*t on me
Jay: no i'm serious. click the link! [It will really suck if he/she doesn't even believe me...]
Person: ur bullsh*t
Person: take that sh*t off
Person: lol
Person: thats preaty cool
Person: lol
Person: i just did that to some1 this week
Person: i went on my friends sn
Person: and did that [those last 8 messages were written in a total of 15 seconds]
Jay: lol cool!
Person: but i didnt know u acn get it published [does he/she know that I merely published it on my own site?]
Person: LOL
Person: This one wasn't as funny, but it was pretty cool!
Person: sh*t i wanna help u
Person: this is fun
Jay: how?
Person: dont know
Person: how do i get the bot
Person: and publish
Jay: [I tell him/her how to make the bot and stuff]. then, if you want me to publish it on my site, e-mail it to [email removed - you can find it on the bottom of this page]!
Person: aight then
Person: ill put u on my list
Person: g2g
Person: im on the phone
Jay: ok cya

Bot : wut up juicy
Person: whose dis ?
Bot: What did you say, [name removed]. Is that from what movie?
Person: ???
Bot: Aight then i'm not going to talk. If you want me to talk again just say talk!
Person: talk ..
Bot: Aight I'll talk.
Person: who r you
Bot: why?
Person: cuase i wanna know
Bot: i just dropped my porn mag. Do you like Star Wars?
Person: joeseph ?
Bot: My penis does not have a response for that. How are you?
Person: who is this ?
Bot: wait...
Bot: this is [name removed], right?
Person: yuh
Bot: Gee, never heard that before. Then again, I never talked to someone this dumb before either. :-p Is the
holding of hands a symbolic gesture for stupid people like you?
Person: z06 sucks d*ck
Bot: I wouldn't even let you touch me with a five foot pole.
Person: whosed i would wanna touch you
Bot: Enough about me, let's talk about my dress.
Person: who da f*ck is this
Bot : hey - no need to curse!
Person: who da f*ck is this ?
Bot : ok, go ahead and curse.
* Bot gets blocked *

This guy was in a chat room, so I used his screen name. Kind of funny, but not the greatest.

aftermath:

Jay (9:06:53 PM): hi. [bot name removed] was just a robot! :-) You can view your published conversation here!
Jay (9:08:53 PM): its the last one on the list. do you see it?
Person (9:09:07 PM): no
Person (9:09:10 PM): ur gay [Umm.... this guy just doesn't get it, does he?]
Jay (9:09:42 PM): why's that?
Person (9:09:56 PM): becuase u dont tell me ur name
Jay (9:10:21 PM): [bot name removed] was a robot. I on the other hand, am an actual person. My name is Jay.
Person (9:10:43 PM): oh ..whoops [It's always great when I get someone who doesn't know much about bots ...]
Person (9:10:43 PM): lol
Jay (9:11:30 PM): it's like a candid camera kind of thing! did you check out your published conversation?
Person (9:11:42 PM): huh ?> [... but this guy is just too much!]
Jay (9:12:33 PM): the conversation is on my web site. you're not the first one to be talked to be [bot name removed]! click here to see what I mean.
Jay (9:13:00 PM): when you go there, your conversation is the last one on the list
Jay (9:14:07 PM): did you see it?
Person (9:14:15 PM): hwo did the bot knew ppl called me juicy
Jay (9:14:30 PM): your profile. 8-)
Person (9:14:47 PM): oh
Person (9:14:48 PM): lol
Person (9:14:50 PM): nice
Jay (9:15:15 PM): yeah pretty sweet

[Bot] : you're christian? - I found this out from a chat room
[Person]: yep
[Bot]: And?
[Person]: and what?
[Bot]: What else do you want to tell me?
[Person]: Lol - The most overused word on the internet! :-)
[Bot]: I am pretty funny, arent I?
[Person]: Um
[Bot]: Er
[Person]: I'm 15
[Bot]: You're A?
[Person]: Sure:)
[Bot]: OK let's do it. Next question?
[Person]: What?
[Bot]: I said OK let's do it. Next question?
[Person]: lol - This is the second time he/she said LOL already!
[Bot]: I am pretty funny, arent I?
[Person]: yes
[Bot]: And?
[Person]: and what? i have no idew hat you're talkign about
[Bot]: What else do you want to tell me? Would you like to have idew hat you are talkign about?
[Person]: its late
[Bot]: I think you mean "it's" or "it is" not "its". I'm awake all the time.
[Person]: i can't think
[Bot]: You can NOT think? Cool!
[Person]: Yes exactly that
[Bot]: I see. I understand. That is "I see. "
[Person]: You're fast
[Bot]: I'm fast?
[Person]: How do you type so freaking fast? lol - LOL count: 3
[Bot]: The keyboard is attached directly to my brain. I'm glad you find this amusing.
[Person]: lol - LOL count: 4
[Bot]: I am pretty funny, arent I?
[Person]: Sure mmhhmm:)
[Bot]: "I am pretty funny, arent I? "? Yes? dude, last time someone said that to me was just as they wiped my juice off their mouth. freaky. Do you speak Spanish? - whoops, guess that just slipped out!
[Person]: Not very much
[Bot]: That is a non-commital reply.
[Person]: I know
[Bot]: You know!?
[Person]: haha
[Bot]: why are u laughing at me ur the ugly one
[Person]: Oh bite me
[Bot]: Yeah that's right. Sorry but I don't have a mouth.
[Person]: lol - LOL count: 5. Is that overuse, or is that overuse?
[Bot]: I am pretty funny, arent I? - Geez, I need to change that!

This was great! Finally a person who actually made my bot seem real! All except for when he/she said "lol", that is. Still, it was really cool!

aftermath:

Jay (10:06:50 PM): hi. [bot name removed] was actually just a robot! :-) Realistic, huh? You can view your published conversation here! It is the last one on the list.
[He/she didn't respond for about three minutes... Why does that always happen?]
Jay (10:09:06 PM): What are you thinking?
[Another minute passes]
Jay (10:10:11 PM): Are you there?
Person (10:11:14 PM): yes [Thank god! (get it?)]
Person (10:11:24 PM): I thought this was a bot too
Person (10:11:24 PM): the othe rone pissed me off
Person (10:11:24 PM): lol [LOL count: 6]
Jay (10:11:54 PM): lol. what pissed you off about it?
Person (10:12:23 PM): it was talking too fast
Person (10:12:38 PM): and too much
Person (10:12:38 PM): and lol yeah [LOL count: 7. Geez!]
Jay (10:13:07 PM): did you know it was a bot at first?
Person (10:13:51 PM): i figured it was
Jay (10:14:26 PM): lol, how come you kept talking to it?
Person (10:15:27 PM): i dunno
Jay (10:15:44 PM): yea, i know, it's late :-)
Person (10:17:41 PM): haha
Jay (10:18:49 PM): alright, cya.
[We actually talked a little bit more right here, but I accidentally clicked the X before I could save it. He/she said LOL one more time.]
Jay: alright, I have to actually go now. (I'm 14 and have school tomorrow!)
Person: okay
Person: lol [This makes a total of 9! Do you think he/she was actually laughing out loud? I doubt it!]
Person: we got out today
Person: have fun
Jay: lucky you... cya
Person: haha [possible 10?]
Person: bye

Here was a pretty funny one, however in the middle of the conversation I selected some text and the program deleted it. That sucked. But there's still some stuff:

[Jay says:] : hey
[Person:]: hello
[Bot:]: whats up?
[Person:]: nothing at all
[Bot:]: That is something.
[Person:]: well i guess it is
[Bot:]: Is it only a guess? Interesting.
[Person:]: who is this?
[Bot:]: Why?
[Person:]: you have the speech of a 3rd grader, however, you type like a secretary - Yes, I have noticed this about the bot too
[Bot:]: I have the speech of a 3rd grader however you type like a secretary!?
[Person:]: ohhhhhh thats a good one bud
[Bot:]: Yeah that's right. A good one bud is a terrible thing to waste.
[Person:]: no doubt playa
[Bot:]: I understand. sorry, i'm poppin a bone here and i might need to do something about it. How is the weather?
[Person:]: mid 80's - notice he ignores the bone poppin'
[Bot:]: You don't have AIDs or anything else I could get, do you? Are we still talking about mid 80s?
[Person:]: how bout you?
[Bot:]: What is it to you. Enough about me, let's talk about my dress.
[Person:]: aight
[Bot:]: I guess you're not too bright, huh? How is the weather?
[Person:]: what color is it
[Bot:]: I think of "it" as having a colorless form, like other pronouns.
[Person:]: k
[Bot:]: Alright then.
[Person:]: once again, who is this
[Bot:]: When? Again, My name is Jay. Who are you?
[Person:]: asfdhranatrj
[Bot:]: riiiight..... What do you like to do?
[Person:]: i enjoy paintballing
[Bot:]: You enjoy paintballing!?
[Person:]: did i stutter?
[Bot:]: I think you did. - see, my bot isn't always incoherent!
[Person:]: k
[Bot:]: Alright then.
[Person:]: alright man, im bouts to up out this biatch, check it
[Bot:]: Alright, [name removed]. Cool, man. Do you mind if I tell other people you are bouts to up out this biatch check it.
[Person:]: i will talk to YOU later jay
[Bot:]: Goodbye. If any of your friends have issues, you can tell them about me and I would be glad to help them too.
[Person:]: nah man go ahead
[Bot:]: "Goodbye. If any of your friends have issues, you can tell them about me and I would be glad to help them
too. "? Not? Cool, man. OK I will.
[Person:]: sweet man
[Bot:]: do you expect me to be turned on about sweet man. But I did not get that. How are you? - riiight...
[Person:]: ttfn ttyl bff
[Bot:]: Goodbye. If any of your friends have issues, you can tell them about me and I would be glad to help them too.
* i sign the bot off so i could publish the conversation without accidentally deleting it again*

I got a few laughs out of this one. This person's screen name was e-mailed in. It's always best when the person doesn't know about bots!

aftermath:

00:52 | Jay: hey - before you sign off, you should know... [bot name removed] was just a robot talking to you! You can view your published conversation at the bottom of the list here: http://www.jayssite.com/stuff/bot/my_bot.html
00:54 | Jay: are you there?
00:54 | Person: ahhh a robot eh...
00:54 | Person: that explains lots of things
00:55 | Jay: lol, yep, so have you heard of IM bots before now?
00:55 | Person: i had no idea... [Yes!!]
00:55 | Person: do you pick people at random?
00:55 | Jay: usually, but you were special
00:56 | Person: so how do i know THIS isnt a bot.... ....
00:56 | Jay: because i actually make sense
00:56 | Person: ahhh i got you
00:56 | Jay: do you want to know who told me your SN?
00:56 | Person: yeah
00:56 | Jay: someone named "Lauren [lastname removed]". ring a bell?
00:56 | Person: lol yeah
00:56 | Person: grrrrrr
00:57 | Person: she'll get it
00:57 | Jay: lol i love this part of the bot process
00:57 | Person: heh alright man..i really must now "be up out this biatch"
00:57 | Person: later
00:57 | Jay: ok cya