The context of the following conversation is Jesse mortgaged their house and gambled with the money, but Jesse lost every penny.:
Jesse says I am feeling horrible about what I did.
The friend responds I heard you lost some money. How did it happen?.
Jesse responds I lost it by gambling it away. I lost every penny.
The friend responds where did the money come from?.
Jesse responds I had mortgaged my house. I can't believe I did that.
The friend responds Wow I am sorry to hear it. You'll get back on your feet..