Relationship money problem

My boyfriend and I have one main problem in our relationship: money. I am a recent college graduate struggling to find a job I enjoy and he is still in college. Luckily for me, my parents still pay for everything of mine…. including my tuition for my undergrad degree, car payment, phone payment, etc.. I have a weekly income from a basic summer job of around 215.00 give or take. My boyfriend, on the other hand, has to pay for everything he has besides his phone payment (yes, including tuition). He gets money from the VA monthly bc his dad is a veteran but he is always broke by the end of the month. I have to help him pay for a lot of things: for example, just today he texted me his bank account went into the negatives bc it got charged for a streaming service so he asked for 5.00 to get out of negatives. Then, I gave him 40.00 in gas money to get to his new work/school and then to my house tomorrow cause when I called he was in the car and his car went on E (we are 1.5 hours away from each other, so gas money sucks too). I guess its fine because I just got paid today and he recently started a part-time job so he should have more money rolling in here soon, but I cant help but to feel annoyed sometimes! He is doing a lot of great things with his life and he even is donating plasma for extra money lately but I cant help but get annoyed when I have to give him 45.00 out of my bank account after I JUST got paid. Like I said, he hates asking and recently got a part-time job so I hope it stops soon. Is this a reason to be angry/frustrated? Should I ask him to pay me back? Usually I do but then he goes broke from paying me back and then I have to help him not be broke and the cycle goes on and on… thoughts?