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.