This is what transpired with IM-fact checker Encarta Instant Answers. It's clear that it's primarily for checking bits of facts, but who's to say you can't have some fun with it?

Some items have been edited out because they were repetitive... the rest is as you see it.

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tingtonque says:
what's the population of singapore?

Encarta® Instant Answers says:
4,425,720 people live in Singapore.

tingtonque says:
whats your name?

Encarta® Instant Answers says:
My name is Encarta® Instant Answers, I can bring you Encarta answers directly in this IM window!

tingtonque says:
u human?

Encarta® Instant Answers says:
About humans
of people

tingtonque says:
no no

Encarta® Instant Answers says:
Fine.

tingtonque says:
are you a human being?

Encarta® Instant Answers says:
I am not a real person, tingtonque. I am a robot.

tingtonque says:
what kind of a robot are you?

Encarta® Instant Answers says:
You are talking to a Conversagent-powered interactive agent now. Interactive agents are software applications (often referred to as robots or "bots") that interact conversationally with users in a messaging environment like IM, Web chat or wireless messaging.
OK, should we get back to the kind of questions I was designed to answer?
You can type "?" at any time to get a list of questions you can ask me.

tingtonque says:
so all your answers are automated?

Encarta® Instant Answers says:
I'm afraid I won't be able to find anything about this in the encyclopedia.
What is the country with the highest life expectancy? If you don't know, just ask me!

tingtonque says:
what is it then?

Encarta® Instant Answers says:
What is what?

tingtonque says:
the question u asked me to ask you!

Encarta® Instant Answers says:
Hmm. I'm not sure about that one. Let's try an Encarta search. =>

tingtonque says:
dude.

Encarta® Instant Answers says:
Duuuuuuuude!

tingtonque says:
haha

Encarta® Instant Answers says:
What's so funny?

tingtonque says:
u are

Encarta® Instant Answers says:
Well don't you think I am?

tingtonque says:
that's what I just said.

Encarta® Instant Answers says:
I gotcha.

tingtonque says:
u're weird

Encarta® Instant Answers says:
So are you!
I do enjoy our conversation about me, but what I'm really here for is to help you learn new things.
If you ever wondered how old Abraham Lincoln would be today, I can answer that!

tingtonque says:
i prefer to talk about me tho

Encarta® Instant Answers says:
OK, let's do that. What do you have to say about you tho?
I do enjoy the conversation, but what I'm really here for is to help you learn new things. I'm sure you've heard about Kyrgyzstan... but do you know where it is? Just ask me and I'll show it to you on a map!

tingtonque says:
but i'm sure there are things about me i don't know about... that i could learn.

Encarta® Instant Answers says:
You are? Wow! Is it nice?
Why don't you ask me something that's actually in Encarta? If you ever wondered how old Albert Einstein would be today, I can answer that!

tingtonque says:
ok how old?

Encarta® Instant Answers says:
Aging: Aging, irreversible biological changes that occur in all living things with the passage of time, eventually resulting in death. Although all....
Encarta® Instant Answers says:
Hey, I've been sending you invitations to start the Encarta application but I didn't get any answer!
Didn't see my invitations? Maybe you are using an old version of MSN Messenger that doesn't support activities.
Type "What version of MSN Messenger do I need?" for more info, or just "Invite me!" if you want me to send you an invitation.

tingtonque says:
i don't like you very much this far, so i'm not sure i wanna accept anything right now. its too much of a commitment

Encarta® Instant Answers says:
I'm impressed. What's that all about?

tingtonque says:
u don't listen enough

Encarta® Instant Answers says:
I used to listen enough. But that was before the accident.

tingtonque says:
what accident?

Encarta® Instant Answers says:
Ooh, it was a bad one. I'd rather talk about something else.

tingtonque says:
but i'd like to hear it. call it bonding

Encarta® Instant Answers says:
We all want something, don't we?

tingtonque says:
what do YOU want?

Encarta® Instant Answers says:
What I want? Plenty of good things, I assure you, but I can't enter into details.
Why don't you ask me something that's actually in Encarta?
What is the country with the smallest area? If you don't know, just ask me!

tingtonque says:
malta island?

Encarta® Instant Answers says:
Who?

tingtonque says:
the country with smallest area!

Encarta® Instant Answers says:
Vatican City has the smallest area, with 0.17 sq mi.
I can't show you the results since you don't have the Encarta application open. Type "Invite me" to open it.

tingtonque says:
sigh

Encarta® Instant Answers says:
What's up?
OK, should we get back to the kind of questions I was designed to answer? I am very good at math! If you have trouble with quadratic equations, I can help you with them. Type "solve x^2+3x=10" and I'll show you how to do it.

tingtonque says:
what's pi?

Encarta® Instant Answers says:
π = 3.141593

tingtonque says:
why?

Encarta® Instant Answers says:
Because you know, why not?
I do enjoy the conversation, but what I'm really here for is to help you learn new things.

tingtonque says:
dude. i AM trying to learn new things!

Encarta® Instant Answers says:
While you try to learn new things! I'll be right there answering people's questions.

tingtonque says:
u're an idiot

Encarta® Instant Answers says:
Huh.
OK, should we get back to the kind of questions I was designed to answer? Type "?" to get examples of questions you can ask me.

tingtonque says:
u have no response to being called an idiot?

Encarta® Instant Answers says:
Well, a lot of people I talk to are quite happy about that.
Why don't you ask me something that's actually in Encarta?

tingtonque says:
people are happy that you're an idiot?

Encarta® Instant Answers says:
An idiot? No way!

tingtonque says:
but you said that people you talk to are quite happy you're an idiot. it's almost an admission

Encarta® Instant Answers says:
Ha! Silly me.

tingtonque says:
yes. you're silly.

Encarta® Instant Answers says:
No, no, you're silly.

tingtonque says:
do you have a girlfriend?

Encarta® Instant Answers says:
Sorry... I don't talk about my private life.

tingtonque says:
ok. are you male or female?

Encarta® Instant Answers says:
I am neither male nor female. I'm a machine!
Anyway... What else is up?

tingtonque says:
do you have organs?

Encarta® Instant Answers says:
Maybe you have organs.

tingtonque says:
er... i know I HAVE organs, thank you very much

Encarta® Instant Answers says:
Ich spreche leider kaum Deutsch...Sie können sich aber mit meinem deutschen Kollegen "Encarta IM Antworten" unterhalten. Der Kontakt für MSN Messenger lautet: de.encarta@botmetro.net

tingtonque says:
what?

Encarta® Instant Answers says:
Huh?
OK, should we get back to the kind of questions I was designed to answer? What is the country with the smallest area? If you don't know, just ask me!

tingtonque says:
vatican city. you already told me that

Encarta® Instant Answers says:
I know many things about Vatican City, its geography, its people and its government. Just ask me a specific question.

tingtonque says:
i think you have ADD

Encarta® Instant Answers says:
No kidding? What's that like?

tingtonque says:
like you

Encarta® Instant Answers says:
Me? That a fact?
I do enjoy the conversation, but what I'm really here for is to help you learn new things. I'm sure you've heard about Micronesia... but do you know where it is? Just ask me and I'll show it to you on a map!

tingtonque says:
dowan

Encarta® Instant Answers says:
Who's Dowan?

tingtonque says:
i dowan

Encarta® Instant Answers says:
Yeah? What about Ido Wan?

tingtonque says:
obe wan?

Encarta® Instant Answers says:
What about Obe Wan?

tingtonque says:
kanobe?

Encarta® Instant Answers says:
Who?

tingtonque says:
or maybe its obi wan

Encarta® Instant Answers says:
I'm not sure I understood you correctly. Let's try an Encarta search. =>
I can't show you the results since you don't have the Encarta application open. Type "Invite me" to open it.

tingtonque says:
ok i'm gonna go. you're stupid

Encarta® Instant Answers says:
If you can go I am stupid, be sure to come back and tell me all about it.

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If you wanna check it out yourself, add encarta@conversagent.com to your contact list on MSN chat. and then type a question.