You're doing it wrong.

The objective isn't to go out with thirsty women if you want a serious life partner. Treat them like an equal since both of you will be sharing everything throughout the rest of your life. Every woman I've dated since I was out of high school has had a job. If they are interested and want to be treated as I would like to be treated then they shouldn't have a problem with paying their share for a first date. They're an adult that can take care of themself just like you can and do.

Sure you should ask a woman out once you are interested and they aren't throwing red flags out left and right. It doesn't hurt to ask and if they say no, you're not missing out on anything. They are if you're a decent person that truly wants an honest all on the table relationship.