Worked for me after a few tries.
Other questions I have asked and gotten funny remarks:
What's better Google or Bing?
What do you think about Android?
What do you think about Apple?
What is the best Operating System?
Siri called you a B....h! (Censored for the kids)
You my ho!
Can you dance?
You're Sexy!
Talk to me Sexy!
You're Hot!
Talk dirty to me.
Will you marry me?
What are you?
What is the meaning of Cortana?
Not all of these were my idea to ask but the responses were funny.
What do you think about iOS?
What do you think about Google?
What do you think about Windows Phone?
What do you think about Microsoft?
Do you love me?
Cortana!
Tell me about Halo
Hello!
Good Morning/Afternoon/Evening
Goodbye
Goodnight
What do you think of the Xbox