I'm dating a wealthy man, but he never has cash and expects to pay when we go out. This isn't fair
How you relate to money, sex and food reveals your character and your relationship to the world. It is, therefore, fair to judge people on how they behave towards these issues.
How you respond to any of these issues from the beginning of your relationship sets the tone and the rules of your relationship. People do not generally change. Nor do the politics of a relationship.
It is important to realise that what you decide to do is going to affect the type of relationship you have with this man in the future. You, therefore, need to be very upfront and have an explicit negotiation about how money and expenses are going to be managed in your relationship. Depending on how that goes, ask yourself if this is a person with whom you feel comfortable, and if he is someone you would like to negotiate with in the future. - Leonard Carr
Clearly you and your boyfriend have a different value system - he apparently is saving everything for himself, at the expense of your relationship.
You are holding onto an old-fashioned value of wanting to be looked after and spoiled by the man on whom you are showering your affection.
At the moment, it seems he invests very little in your relationship except his time. I wonder how much time he would give you if you stopped paying for everything? If he is not prepared to pay his way in this relationship, why are you wasting your time and money on him?
Are you going to benefit from his investments? Have you seen his investment portfolio? Who says he is not up to his ears in debt rather than money? - Stephanie Dawson-Cosser