Should I break up with my fiancee?

All I myself can do is offer my opinion on what I would do in this situation. You need to sit down and talk with your fin'. Either he is with you or he is with his "other" family. It sounds as if his mother has done everything for him, and she has him under her wing, and she uses her powers to control him. I would be cautious about entering a relationship with someone who does not want to commit themselves to bettering the future together with their partner (you). He is acting like a teenager and not giving any thought to his future. A loss of $1000 is a great set back. Look at you and him as a family, and is there talk of a future together or is he he just acting like a teenager who is out on a date? If you are not feeling secure about your future together, express your feelings to him now before it goes any further. You don't want to end up 5-years from now, feeling the same way. I myself would ask for changes to be made, or I would be gone. Time is precious.