Here's that question

You know, one of my very best friends has a guy just like that. Like when we took her out for her birthday (a big group) he did not contribute a dime toward her meal, or even toward his own meal. We all had to pay. Even on their first date, he not only didn't offer to pay -- he didn't even pay for HIS OWN meal. He insisted that she pay. He is a very, very cheap man. But, she loves him, and she married him...
I dated a guy who was a student, and I certainly wasn't wealthy, but he kind of expected me to pay for everything too. Which, was weird. It really doesn't sound like you're in sugar mama position. But, maybe you guys could just do stuff that's free. There's a lot of free things in the world. (If you really like him.) My friend and her husband go for a lot of walks...

It doesn't sound good -- he sounds not merely cheap, but sneaky about it, which is worse. ..
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However, if you really like him (although you haven't said that you do really like him), I'd ask him what the problem is. There's unlikely to be a good explanation, but maybe there is -- so you may as well hear him out rather than just dumping him straight away...

I think you need to ask him abotu it...It is unfair for him to not at least pay his half...OR make sure he knows you are not made of money and can not afford to keep paying for the both of you...

As someone who formerly made almost a career out of dating musicians, girl, I feel your pain. And I am not a materialistic person, but sometimes it's just nice to get treated and not have to go Dutch--or in your case, pay 2/3! ..
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He probably is not proud of not having money, so I'd suggest, if you dig this guy, try to do things that are free or cheap. Go to the park with your dog, watch a DVD together, etc. But on the other hand, is he trying to do nice things for you, or is he stingy/closed off in more ways than one? It can't be all you paying for activities, planning them, etc. He has to participate too...

I'm a little bit old school hun! I couldn't imagine letting a woman pay for anything!..
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What a cheeky so 'n so! In my experience with frugal people, if they are usually tight with their money, they are usually tight with everything else!..
If I was him I wouldn't have gone anywhere that cost anything, I know money is hard to come by but that, that just takes the mick!..
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Have you tried dropping hints or talking to him directly? I'd find it embarassing to let my freinds meet a s/o like that! Maybe tell him tha you're uncomfortable with him being so frugal, tell him that you're not superficial. But that his actions are fairly disrespectful to you and your friends!..
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Maybe it's a sign of deeper issues like the way he was raised? Difficulty growing up, or scared of losing everything! Is he contributing to you emotionally? Are there any signs where he isn't sure or frightened?..
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I wish you well hun!..
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All else fails, go your seperate ways!..