When investing you have the chance of losing any money you've made from the investment as well as the original amount you put down. When saving you are simply putting aside money and beginning to pile it up as you continue to save it.
Answer:
Before this conversation took place "person 1" was always losing to "person 2"
"Person 2," said. "I can't remember the last time I didn't win"
For the citation for box 3 is:
"Are you going to be on later? I'm going to win this time."
Hoped this helped!