Should broke men date?

I must extend sincere apologies to my faithful readers who have been wondering what the hell is going on in The Dating Lane. There has been some serious bumper to bumper traffic which led to quite a few fender benders, but for the most part, additional life responsibilities have gotten in the way of me chronicling my dating experiences. But please believe they haven't ceased! I have tons of blog fodder!

So, I met this guy; a really nice guy. Charming, well-educated, handsome and ready for a relationship. He and I have been acquainted for quite a few months now and have been kicking it hard. The down fall? He's broke. And he knows it.

He isn't your ordinary broke dude though; he is one with potential. He is a student and soon he will be making mucho dinero. But for the time being, he's a baller on a budget....a SERIOUS budget. Here is where the problems lie. Being that he is a baller on a budget, should I be understanding of his financial woes and reach for my pocket book when the check comes, or should I reach for my pocketbook and walk out of the door?

We've been on quite a few dates, each of which I've contributed financially to in some form or fashion. From paying for parking to buying a round of drinks- I almost feel obligated to do so. After all, I have a pretty decent job and make good money, and he is- well- a student.

Should men with financial problems date if they can't afford to?

If you're a faithful reader of this blog, then you know my position on going dutch. I don't believe in it. I despise it. Most of you know how I feel about men not being men and not treating on the first few dates. But I think I've become weak :( I see the potential in this young man, and I understand his struggle. I sometimes feel as if I must contribute to our date when we're out. Why? Well, because I have a job and he doesn't. And frankly, I don't want him to feel as if I'm using him for a meal or some drinks. As I stated, I like him.

One of my good girl-friends and I were discussing this and she opposes my outlook. Though we don't agree on my position, she had a valid point. She told me that I should not settle for him even if I see his "potential" because I am far too old to be dating "potential". I do concur with that statement, however I feel as if his financial situation is less than 20% of the issues we have. Well, that and his lack of aggression- but that's another blog for another day.

This moral dilemma has definitely been rearing its ugly head as of late. I have found myself going out on dates with other guys who will foot the bill, only to diss them soon after the meal and a few cocktails to go and hang out with Mr. Baller on a Budget- at his apartment. I have definitely been a user. Hell, going half on a date has become quite expensive!

I have never dated a dude with financial problems. Even in high school, my bf at the time was a college student who waited tables in a popular restaurant. At a young age I was dining out at his expense on a regular basis. My post college bf was young, rich and fabulous and would never have cringed at the thought of letting his lady pay for anything. So, I'm pretty spoiled. I also have a doting father, who took my sisters and I out on a regular basis to 5 star restaurants. My dad (to this day) is the epitome of a MAN and instilled in us early on that if the man in our lives couldn't do as he did for us or better, we had no need for said man. He set the standard by which all men were to follow. On the flip side, my mother did support my father throughout his days of law school, as she had already gotten her post graduate degree and was the bread-winner at the time. However, they were in their early 20s too.

So as you can see, I am so conflicted! I don't know the right answer to this. Should I stick it out and continue to date him, even though we can't really date because of his financial situation? Or should I drop him like he's hot and move on without "wasting my pretty?" I'd love to hear your opinions on this matter.

Have you ever dated a baller on a budget? How would you handle the situation if you were me? Is this entire top shallow to you?