Can I be totally honest about his career prospects?

When you said that "He quit his job and invested his time to a career he knows only a small percentage of people can make a living at," you weren't specific, but immediately I knew you were talking about writing...later on in your post you confirmed my suspicions.

It seems like a lot of folks these days cling to this fanciful dream of being a writer. But you know what? I was a freelance writer for a short time, in between having a full-time job and going back to school. And let me tell you, I can tell just by your description of your boyfriend that he's not going to make it.

I worked hours a day on lousy assignments and got paid peanuts. I plugged away at short stories but never got one published. You know how hard it is to get a short story or a novel published? Just think about how few people read short story magazines (next to none) and novels (only bestsellers mostly)...now, think about how well such an unsuccessful industry pays. In case you haven't guessed it, the answer is: not much.

I knew some guys who were making a living solely off of writing, and it is hard, hard work. I can't stress that enough. It's hours of toil and little reward. And most people simply aren't good enough to make it...a sobering fact, but a true one.

Okay, I think I've made my point. The thing is, if your 29-year old boyfriend still harbours these boyhood dreams, he has to wake up fast. It doesn't mean he has to be miserable...I transferred my love for writing into what will hopefully be a successful career in academia (I'm still working hours and hours, but even my scholarship money pays better than freelancing). All your other problems with him aside, this is an issue that needs addressing.

Don't mean to be blunt, just want to spell things out clearly.