I'm looking to visit my boyfriend. Can you help me find a flight/
Where are you departing from?
Pittsburgh
Where are you going to?
Chicago
On what day do you want the plane to arrive?
Maybe Friday? Have you ever been to Chicago? It's my favorite big city!
What day of the month is Friday? I have never been to Chicago.
Friday will be the 29th. Any time or price is fine. Let me know what's out there!
Right, I found an Economy flight with American for 434 credits
 that takes 5 hours to get to Chicago.
That sounds perfect. You should really visit Chicago yourself. I recommend Millennium Park.
May I have your name, please?
Alina
The flight is available. Should I reserve it for you?
Yes, please do! 
I'm sorry, but your reservation request was unsuccessful.
Try again? Sometimes technology can be flaky.
I'm sorry, but your reservation request was unsuccessful.
Oh, well. Thanks for trying. That's all I need! Thank you and I'll see you in Chicago sometime!
Thank you and goodbye.