Annie's Mailbox

Ask Amy column

Q. My boyfriend is a loving, creative, and sensitive person who is 15 years my senior. (I am in my mid-30s.) When we met, I was going through a hard time emotionally and he was going through a hard time financially. He helped me out by being supportive and understanding and I helped cover his bills.

Fast-forward to a year later. I still struggle with my ups and downs, and he is still broke. I have continually asked my boyfriend to get a job. I know he’s trying, but even a part-time job at a convenience store would help keep us afloat. We live together, and I know that he spends many productive hours on projects that may or may not eventually pay off.


His former profession as a freelance producer dropped off with the economy, and while he tries hard to find work in his field, he is extremely reluctant to accept the fact that he may need to get a “regular” job.

Besides that, he is always home, so I never get any time to myself. Both the financial problems and lack of alone time make me testy and occasionally hysterical.

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I love him very much, but I can’t continue to keep my frustration bottled up. I tell myself I’m going to leave him if he doesn’t find work, but I really want to stay together. How should I handle this?

Round the Bend

A. The way to handle this is to introduce some clarity into your conversations. Don’t wait until you blow up; do this when you feel calm and prepared.

Having been a freelancer for many years, I assure you (and him) that the very essence of freelancing is that you have the freedom to accept a variety of jobs, as well as the responsibility to make a living between gigs. Freelancers teach, tend bar, work retail, and do whatever it takes to bring home the dough. Volunteering is also a wonderful way to keep busy, creatively stimulated, and to meet new people.


You also need time to yourself at home. This would probably help both of you. Tell him that because he has a lot of privacy during the day you’d like some solitude, too — maybe one evening a week and a weekend morning. He needs to step out and get going.

Q. I’m 75 years old, single, and have two sons. One son has been hostile for years — with outbursts directed at me. The other has emotional and slight mental health issues but regards me as a treasure.

I’m contemplating leaving most of my assets to the latter. I know he isn’t the best money manager, but he probably will need more money (and I feel closer to him).


A. It is your money and you should disperse it exactly as you please.

I have two suggestions: Make sure to take care of yourself first. You may need to spend down your assets in order to support yourself through unforeseen challenges.

Second, do not discuss this with either son. They may pressure you for information. Your choice may change over time and the last thing you want is to open this up for conversation (and possible manipulation).

A trusted lawyer or neutral financial adviser could help you navigate this, and provide a buffer if you need it.

You should pick up the book “Smart Women Protect Their Assets: Essential Information for Every Woman About Wills, Trusts and More” by Wynne A. Whitman (FT Press, 2008).

Send questions via e-mail to or by mail to Ask Amy, Chicago Tribune, TT500, 435 N. Michigan Ave., Chicago, IL 60611.
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