What does 50/50 mean?

For the most part, I consider myself some sort of enlightened, non-traditional woman. I think one of the main reasons I didn't learn to cook much was because I was somehow scared of getting stuck into that role. I'm not sure why, I fully realize cooking is an amazing skill. In dating and thinking about what I want in marriage I've come up with all sorts of fair ideals, such as wanting a man to help out with the housework and me not wanting to change my name, if it ever came to that. Apparently I don't want a traditional role, but I'm not completely liberated either.

Now I find myself dating a guy who believes in 50/50, at least, I think, in terms of who pays for stuff. The first sign was when he let me pay for the tip on our first date. No big deal, of course, but still it hasn't been the norm. On our dates he's mostly paid, I've paid for a few things, but it has somehow felt a little more of a question than has usually been the case. His position became a little more clear when we were talking about exes and he started talking about his and how she wanted to go on vacation but didn't have money...so I don't know if this point was a deliberate illustration for me. It sounds like he's been burned in the past in this arena.

Last week we are watching TV and there was a commercial with a beautiful beach, and he was like "Let's go to Jamaica! Or somewhere warm!" No talk of money at this point, and I figured I could get us some deals with my flight benefits. Standby flights were all full because of the holiday weekend, so we looked at some package deals. I researched stuff on the computer for hours. Nothing was cheap and what we finally came up with ended up being more than I could personally pay, which I told him, and he said it was up to me, he understood either way, that he was under financial stresses (his way of saying he couldn't pay for any of my way), and that he was a 50/50 guy. I said that was fine, I understood, it was more than I could do, but maybe with more notice we could do something another time. I also attempted to explain a little bit of my situation-that I don't make much money, but that the benefits are worth it to me, to have the lifestyle I want, and to be able to travel for less, as well as helping others in this way too, though it didn't really work out that way this time.

So I'm just trying to figure out my feelings on the topic and what I think is fair and what I am comfortable with. The 50/50 ideal might be great if you are both single professionals and make a comparable amount of money. But what if one person makes 3X plus what the other makes? Is a 50/50 split fair in that case? Is it just too bad for the one who has chosen the job that doesn't make enough? Maybe in the beginning while 2 people are trying to figure out whether or not they want to be with each other 50/50 is okay. But isn't there a time, eventually when I becomes we? When you want the person you are with to enjoy things that maybe they couldn't enjoy on their own? Is that selfish of me, wanting to keep my low-paying job, and then merge finances with someone later, which would obviously be to my benefit financially?

I think there are other things that have equal value to money. I have no desire to be exactly like this, but in my parents marriage, my dad makes the money, my mom cooks, cleans, washes, etc, for him, so though she is not making actual money, she is still providing, just in a different way. If I spend hours planning a trip, shouldn't that count for something? But then if you're keeping track of 50/50, how do you not turn everything into a "what's it worth controversy"? Maybe it is too much for each person to just attempt to be generous in their own way. Maybe these kinds of conversations are normal to have, it just seems so awkward to me.

Thoughts? Suggestions? Experiences?