my boyfriend and I are both 21. I have a job and I drive everywhere. he doesn't have a job nor a car. So I tend to feel obligated to pay for the both of us since I have money. I always initiate paying for the both of us every now and then. He hardly steps up and pays for the me but he will pay for himself most of the time so I won't have to pay. I wish he would step up and pay a little more often like how it should be. I told him he needs to get a job and although I hate telling him that, I think it's a little unfair for me.
There's no "should", it's just whatever works for you and your partner. I think it's good to be willing to pay your own share.
However, my boyfriend makes significantly more than I do. He's pretty well off. So, though I've offered to take turns or split it and don't have an issue with that, he told me from the start not to worry about it. And I feel silly insisting when it's clearly not a big deal to him. He's said he'd just rather focus on us having a good time than who pays for what, and I respect that. It works for us I guess, and I appreciate it whenever he takes me out.
On your situation, I understand your frustration. You should talk to him. You're not comfortable doing most of the paying, and it's important that he get a job not just because of that, but also to have his own independence.
You've not asked a fair question in either the title or text both of which seem to contradict the other. You ask if guys should always pay yet you say you're currently always paying yourself so you much accept that's not the case.
One person shouldn't pay for everything. Regardless of gender both should contribute however you are the one with the job and money. It's is a sad reality of some relationship that one cannot always contribute but demanding someone who has no money pays isn't going to get you very far. In fact at best it'll probably make him feel bad and at worst you'll push him away.
Trying to find him a job might help but you didn't really explain anything else. Is he in education or just currently out of work? Has he had jobs before and if so did he leave that job by choice or because of lack of work?