Talking about money

My boyfriend and I have been dating for several years and overall, we have a great relationship. He is kind, caring, smart, and hard working. We first met when I was just out of college, at which point I proclaimed I didn't want anything traditional (marriage, house, kids) in my life, just freedom and fun. A few years later, I'm not exactly sure what I want, but I know I want those options -- in case they become what I really want. So I started talking and asking.

Problem is, whenever I try to talk about planning for the future, we wind up in epic fights or having disappointing attempts at the conversation. Ultimately, I'm not trying to make life decisions, I am trying to make sure I have the ability to make whatever decisions I want when I want to make them, so I'm talking about financial freedom.

I would never ask him to leave his field. I am so proud of all he has accomplished and confident in his career. We will have disparate incomes, which I'm OK with, but he is very sensitive about it. He has some bad debt (at no fault of his own) and I want to address it head on. He wants to kill me when I bring it up. He feels like I'm lecturing him or coming down on him. He thinks I am telling him he's not doing enough, even though I've explained a million times that's not what I'm doing. I'm just trying to act as a team.

It's tough because I feel like conversations about the future should be fun and exciting, even if there's baggage we have to sort out. I am not questioning whether or not to be with him -- not at all -- and I'm sure we can get past this. But how?

– Spontaneous Planner, Boston

It seems to me that you have to decide what you mean by "team" before you have these conversations with your boyfriend.

Are you trying to help him with his debt as a girlfriend? As a potential wife? As someone who'll be splitting expenses with him for years? I understand that you just want options right now, but it's difficult to make a financial plan with someone who is an almost-partner. If you really plan to stick around for good, with or without a title, you might want to make sure he knows where you're coming from. Right now, you're just a girlfriend with opinions.

Also: Are you at a place in the relationship where you'd feel comfortable taking on more expenses so that he can pay off debt? Are you willing to make a financial contribution to the partnership? If you're really a team, are you open to paying more than your share? Give that some thought.

Conversations about the future can be fun and exciting if it's pretty clear that two people really have a future together. If you do a better job defining your commitment -- and he's on board with the plan -- it should be easier to talk finances. It's time to be clear about your intentions.

Readers? Is this about the awkwardness of money talk or about the lack of clarity in their commitment? Should she help him financially? Are they really planning as a team? How should she approach these issues? Help.

– Meredith