Are we approaching a dead end or are we already there?

My boyfriend and I have been dating for about a month and a few weeks now. I really care about him and like being with him, but time seems to not be on our side. In May he will be graduating highschool, while I still have another year to go. Due to some private legal matters, he has a court date next week and might go to jail if he can't pay the fine, which I am still wondering about whether I should help out by offering to pay the fine, since his family is going through hard times, especially with money. For these two reasons I have been trying not to get too attached. So, should I take a chance and make the best of it, or quit it while we're waiting for possible time bombs? I don't want us to break up, but I might I it's in our best interests.