Kaylee works for a collection agency. It's something she started for herself after getting out of debt years ago. She has many clients. Some of them are rich. Some of them are poor. Will just so happens to be one of the rich ones. Which is great for Kaylee. When he pays his debts. Now he is asking for an extension, so he doesn't get in trouble. This wouldn't be an issue, but Kaylee doesn't quite trust him.