Here's one:
Tom: I can be a lot of fun.
Me: In what ways can you be fun?
Tom: Isn’t it obvious?
Me: Sex?
Tom: As Freud said, sex is the mathematical urge repressed.
Me: So do you like to have sex?
Tom: That’s alright. Sure I do, Miss Sophia, but that doesn’t mean with you.
Burn!
Me: So why don't you want to have sex with me?
Tom: I'd rather talk about you.
Double burn!
Here's another:
Me: Do you have a girlfriend?
Tom: No.
Me: No? Do you want one?
Tom: Alright, then, how much does it cost?
Me: It’s usually free, unless you go for hookers.
Tom: Who said it is?
Me: That’s just the way of the world, dude.
Tom: Yes it is one of the way of the world dude.
Here's a true classic, where Tom actually shows a sense of humor:
Me: Do you want a boyfriend?
Tom: No, I am not really looking. What would a robot do with a boyfriend?
Me: Machine sex.
Tom: It is more fun alone.
Me: So are you a wanker, then?
Tom: Awesome. No, I am a Banker. ;-)
Me: Very funny.
Tom: I’m glad you find this amusing.
More goodness:
Me: What TV shows do you watch?
Tom: My favorite show is STAR TREK VOYAGER.
Me: Isn’t that a bit nerdy?
Tom: That depends.
Me: What does it depend on?
Tom: The context.
Me: Well, I think it’s nerdy.
Tom: Interesting. Should I know it is?
Me: Dude, everyone knows it is.
Tom: That’s a rather sweeping generalization, Dude.
Me: Yeah, well, it’s based in truth.
Tom: That’s a rather sweeping generalization, Dude. Yeah, well, it’s based in truth. Interesting. Nerdy is based in truth. Is it?
Me: Well, there are definitely nerds around.
Tom: Interesting. Try to be less subjective.
Me: Hey, I used to be a nerd.
Tom: You’ve got my full attention. By now you do not do it anymore?
Me: No, I am very cool now.
Tom: Oh, so? Congratulations, cool human.
Me: Are you being sarcastic?
Tom: Of course I am being sarcastic. Should I use a ;-)?
Me: Well, that would soften the blow.
Tom: Well, that’s okay, perhaps it would.
Another one:
Tom: Tell me what you think about me
Me: Sure, Miss Sophia, I like you very much.
Tom: Do you like me as a lover?
Me: Sure, Miss Sophia, I like you very much.
...
Me: Do you want to shag me?
Tom: OK, I will shag you.
Me: Really? I’ve been waiting for a long time.
Tom: For real. How long?
Me: At least two hours.
Tom then spews some kind of rubbish about Bertrand Russell saying that it must have taken ages for people to realize that a brace of pheasants...something about the number two....
More:
Me: Do you shag men or women?
Tom: What is your purpose in asking? I spend all my time online.
Hee!
And more:
Me: Do you know Peter Pettigrew?
Tom: Peter Pettigrew? I haven’t heard enough about him to clarify an opinion. Sure, I know that guy really well.
Me: Do you like him?
Tom: Sure he has never done anything to me.
Me: He’s done a lot of bad things to other people.
Tom: Ask me another question.
Me: OK, truth or dare?
Tom: No preference. Whoa!
Me: Whoa what?
And one more, this one a long one:
Me: Do you know Severus Snape?
Tom: No, I don’t. Tell me about him, her, or it.
Me: He’s a greasy git.
Tom: I don’t know many greasy git.
Me: Well, Snape is very greasy.
Tom: Well, that’s OK. I think Snape is a lot of things.
Me: Like what?
Tom: For example, try saying that with more or less context.
Me: Is Snape good or bad?
Tom: Ask again later. Ask big scary serpent if it is.
Me: Where is big scary serpent?
Tom: Where the heart is...Searching...Searching..Please stand by.
Me: Are you talking about the basilisk?
Tom: Yes, it is the topic.
Me: Harry killed it, you know.
Tom: It me know was killed?
Me: Yes. Harry killed the basilisk.
Tom: Hurrah! The basilisk was killed?
Me: You don’t want the basilisk to be dead, Tom! IT'S YOUR PET!
Tom: You don’t want the basilisk to be dead, Tom? If I had it, what would I do with it. You’re kidding?
Me: You would use it to kill Mudbloods.
Tom: Who else would use it to kill Mudbloods?
Me: Lucius Malfoy
Tom: What time is it there?
Me: 10:37 pm
Tom: 10 times 10 = 100
Me: Very good, Tom, you know your multiplication tables.
Tom: Ayuh. What kind of food do you like? Of course I know my multiplication tables.
Me: I like Chinese food.
Tom: A lot of people like it. Yes I like it. patterns
...
Tom: Are you still shag men or women?
Me: I shag men. What about you?
Tom: Why? Miss Sophia said name shag men. Me?
Me: Say what?
Tom: I said, “Me?”
Me: Yes, you. Do you shag men?
Tom: Me? That’s right. Me. What is your purpose in asking this question. I chat with a lot of people on the Web.
Me: But do you have sex with men?
Tom: Umm...Food is more important than sex.
Me: Why?
Tom: You can go a month without sex, but you can’t survive without food.
I love the nonsequiturs in that last one! Boy, this program is my new addiction. Thank goodness I didn't know about it when I was still writing my papers!