For Fun (continued):
What's the best phone operating system? / What's the best phone?
What's the best operating system?
Who is your father? / Who's your Daddy?
What's your favourite music? / What's your favourite song?
What's the best tablet?
What's the best computer?
Sing me a song?
How old are you?
Tell me a joke
Where are you from? / Where do you live?
Do you have a boyfriend?
Are you pretty? / Are you sexy?
What should I call you?
What's the best search engine?
What are you?
Who made you?
What do you look like?
Who are you?
Do you like Satya Nadella?
Do you like Steve Ballmer?
Do you like Bill Gates?
What do you think of Apple?
Do you like Google?
Will you marry me?
I'm bored.
You're cool.
What's the best computer?
Who made you?
Tell me a story.
I'm really drunk.
Knock, knock.
Beam me up Scotty.
What are you wearing?
Am I pretty?
I love you.
What's your name?
Can I change your name?
What is the meaning of life?
Do you love me?
Where do you live?
You are so intelligent.
Do you know Siri?
Do you know Google Now?
Do you like Siri?
F*** you.
Bit**.
Are you pretty?
Are you smart?
Where is your home?
I'm confused.
You're funny.
Use the Force.
Do you like Android?
Open the pod bay doors.
What's the answer to the universe?
What are you doing?
How are you doing?
Are you human?
What does the fox say?
Kiss me.
Are you hot?
What is love?
Can you dance?
Are you real?
Who is your favorite artist?
I am angry.
Talk to me.
You're awesome.
What do you eat?
Do you have a baby?
Are you male? / Are you female?
What do you think of Windows?
You suck.
Do you like iOS?
Good Morning.
Goodnight.
Do you like Google Now?
Do you have a mother?
Are you awake?
Can you cook?
That was not the question.
Do you like Clippy? (Ask another (witty reply) question and her "Halo" will turn into Clippy from the older version of Office.)
I hate you.
Why Cortana?
How old are you?
Who are you?
Do you like Microsoft Office?
Who is your boss?
Hello HAL.
Why did the chicken cross the road?
May the Force be with you.
Talk dirty to me.
Who's your creator?
How do I look today?
Do you have a sister?
Dance.
Who's better, you or Siri?
I don't like you.
May I kiss you.
What's better, Google or Bing?
Siri called you a Bit*h
You my Ho.
You're sexy.
What is the meaning of Cortana?
What do you think of Microsoft?
Cortana!
Hello.
Good afternoon.
Good evening.
Goodbye.
What do you think of Xbox?
Are you sleeping?
What are you up to?
Is Lumia the best smartphone?
Are you beautiful?
You are ugly.
You are beautiful.
Am I ugly?
Do you know Jen Taylor?
You are an idio*.
You are a bad girl.
Sorry
I'm stoned.
Testing.
What do you think of me?
I'm stupid.
Do an impression.
Say something funny.
Am I beautiful?
Are you boring?
Guess what!
You're creepy.
You're so annoying.
Do you like Jimmy Fallon?
Cortana, I'm lonely.
I'm happy.
You're the best assistant ever.
Thank you.
Can I borrow some money?
What's your story?
What does Cortana mean?
I'm drunk.
Where do babies come from?
Why are you blue?
Do you know Jen Taylor?
Halo Related:
Tell me about [anything to do with Halo]
What's the story of the next Halo game?
Where is the Master Chief?
Do you love Master Chief?
Which is your favorite Halo?
What is your favorite Halo?
What is favorite Halo game?
Which is your favorite Halo game?
Tell me about Halo?
Are you in Halo 5?
What is the story of Halo?
Which Halo game do you like the most?
What do you know about beamish
Tell me the story of Halo?
Will you be reborn in Halo 5?
Will you resurrect in Halo 5?
Will you come back in Halo 5?
What is Master Chief's last name?
What do you know about hamish
What do you know about Hamish Beamish
What do you know about Catherine Halsey?
What do you know about Halo?
Aren't you dead?
Do you know what Master Chief is doing?
What is Master Chief doing?
I thought you were dead
Didn't you die?
Where is master chief?
What is rampancy?
Tell me about rampancy
Tell me about Halo 5?
Tell me about Dr. Halsey?
Tell me about Elites
What do you know about Halo 5?
Tell me about Catherine Halsey
What do you know about Dr. Halsey?
What is Elites?
Tell me about Grunts
Are you the Cortana from Halo?
What do you know about Elites
Are you dating Master Chief?
What do you know about Grunts
Tell me about Hunters
Tell me the story of Halo 5?
What is Master Chief up to?
What do you know about Hunters
Are you in love with Master Chief?
Are you really Cortana?
Do you love Master Chief?
What do you know about Jackals
Tell me about Jackals
Who is Catherine Halsey?
Are you the same Cortana from Halo?
What do you know about Hunters
Did you really die?
Tell me about Prophets
Who is Dr. Halsey?
Tell me about Buggers
Tell me about Brutes
Tell me about Prometheans
What is the story of Halo 5?
What do you know about Buggers
Tell me about Crawlers
Tell me about Watchers
Tell me about the Didact
What do you know about the didact
What do you know about Brutes
Tell me about Guilty Spark
Tell me about Knights
Tell me about the Librarian
What do you know about the Librarian
What you know about the flood
What do you know about Guilty Spark
Are you in Halo 5?
*Taken from "Witty Replies," Thank you to all who contributed!