How should I resolve this problem with my boyfriend?

Hi. I’m writing here in order to get some opinions on my situation with my boyfriend before him and I try to resolve the problem tomorrow. The situation almost seems silly, however, it’s been making us feel disconnected in the last two weeks.

Basically, my boyfriend is currently in college and rents out a room in a house to live. He’s been pretty tight on cash in the last year, so we haven’t been able to go out together much as he has to pay for his school and rent. I am fortunate to be able to live at home while I attend university, so I am not as financially tight. So, my boyfriend and I usually spend our time together at his place, and sometimes we will go out for a coffee. I don’t expect him to take me out for dinner often because I know he does not have the money for it. Instead, I have taken him and bought him dinner a few times since he’s moved into the new place, and I always insist on paying my own tab to help him out.

The problem though, is that in the last week, I’ve been feeling very upset about the fact that we hardly go out. I love spending time with him, no matter what we do, but I feel it’s important to go out and do things together once in a while in a relationship. I’m sure we’ve only gone to dinner about 5 times in the last year. What’s upsetting is that I suggest to go for dinner often, even for an inexpensive meal at, for example, Swiss Chalet. Dinner there is about $15 each. However, my boyfriend’s reply is always that he does not have enough money.

What bothers me.. is that sometimes he does have some extra cash, and although I completely agree that he should treat himself to a blu ray, a game or whatever he likes.. I feel a little bit hurt that in the last year, he hardly ever spends that extra cash to go out with me on a date. Even if I pay for myself. I’ve been upset about this, and he can tell. However, he feels that I don’t ‘understand him.’ I haven’t told him how I feel, out of fear that he will take it the wrong way. I believe he already feels that I am expecting him to buy things when he doesn’t have the money. But it’s not that. I understand that he is tight, but I’m a little hurt that he never thinks to take me out with the extra money he has once in a while. It seems he’d rather buy a new video game with his money than put some aside to do something with me. And it’s been a YEAR since he’s had the money problems. I’m sure he could have put $15 aside every now and then to take me to Swiss Chalet.

I need advice on how to approach him with how I feel, without him taking it the wrong way. I don’t want him to feel like I don’t understand his situation. I need him to understand me and get where I’m coming from.

Any tips? Do you think I’m in the wrong? Any opinions would be great. Thank you.