The context of the following conversation is Skylar entered the contest because the top prizes was a massive cash rewards which he really needed.:
Skylar says I hope I win the contest because I really can use the money..
The friend responds What are you going to do with the money if you win?.
Skylar responds I am going to use it to get a new car, maybe a new house and take a trip.  I'm tired of renting and my car needs so much work, it doesn't make sense to keep it..
The friend responds Do you really think you have a chance at winning? It seems like a lot of people have entered the contest..
Skylar responds I know, but I've just got a good feeling about it.  I'm due for a break..
The friend responds Well, good luck.  If you win, we'll go out and celebrate..