Honestly, you might just want to tell him, "Dark Boyfriend, I'm not your mother and I don't want to be a jerk, but you're making me feel like both every time I remind you to file for unemployment/apply to college because you haven't done it yet."
But the other facet to that conversation probably ought to be asking him what he needs from you in order to successfully do both of those things. Essentially, your current MO (reminding him) is not getting anything accomplished, so it's his turn to think of a plan of attack. Put the onus on him for finding a solution to the problem of the unemployment and college application.
I think the other thing you might want to bring up is that, while the unemployment and school are primarily his concerns, they do affect you. Particularly if you live together, the unemployment will have some very real financial impacts. But even if you don't, it matters. Even though school isn't going to affect your income in a positive way, it does have an affect on your future together.
Finally, try really hard to be open-minded and listen to him when you ask him for his ideas for a solution. Be prepared to push this issue so that the root cause (if there is one, and if he knows about it) comes to light.
Personally, I have found that when my husband doesn't step up and do things that I expect of him, 75% of the time it's because I have a tendency to be controlling and make it hard and rather unpleasant for him to take charge of anything. My knee-jerk is to assume that he doesn't know what he's doing and that I can do it better, which is insulting and generally not even true. It's taken some effort on my part, but he's a lot better at following through on the things he says he'll do now that I am less likely to get mad at him for doing it wrong or take over because of perceived incompetence.
I have no idea if that is even a remote possibility for your situation, but it's worth trying to be open to the fact that there may be something you need to change that you just haven't figured out yet, and that Dark Boyfriend might not be willing to bring up unless pressed.