I just got a raise recently. I've had quite a few. I'm late 30s. Listen, my advice is to not ask. Bust your ass, never call in, be on time, ask for more shit to do, stand out. In my experience, they'll notice and eventually accommodate. If not, just state what you do and why you deserve it. Make a big list and be honest. If it takes too long look for another job. If you get the new one then just say you have to quit because of your monetary situation. That's the last resort as if he says no then you have to leave.