First, I want to point out that it was very smart of you to seek legal advice about this issue because your boyfriend's case appears very complicated. Second, I should warn you about what you disclose on this site could possibly be viewed by the government, which may be in the process of attempting to deport your boyfriend or place him in removal proceedings. That being said, you should meet personally with an immigration attorney who also handles criminal matters for immigration clients. This is not a simple issue; therefore, there is not a simple answer. If money is an issue, seek an immigration attorney who provides free initial consultations and take as much documentation and information as you can when you go to meet the attorney. Finally, I'd like to point out that marrying your boyfriend will not solve the matter completely, but it could prove to be helpful. The same applies for your boyfriend's education and prospective occupation and the fact that he's been living in the United States since he was five years old. Again, these factors do not solve the problem, but may help the situation.