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Portrait of advice columnist Amy DickinsonAuthor
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Dear Amy: I love my fiancée. We’ve been together for five years, living together for three. During that time, I’ve helped her by paying the majority of our living expenses (rent, car insurance, cellphone, etc.), so she could focus on paying off the debt that was looming over her before we began to date.

She is now almost debt-free.

She had a full-time job several years back and even contributed a little toward our basic bills. Since moving in together, our living expenses have increased, but she has failed to find a full-time job or get her business off the ground.

I’ve had numerous conversations about the bills and helping to save for retirement, but she has failed in this regard.

She has had about eight part-time jobs in the last three years, but is currently unemployed. I’ve tried to help her but I’m concerned about her lack of initiative and motivation.

My family and friends have told me she is using me, and that I am just enabling her.

I can’t just make her split our bills fifty-fifty or have her sign a contract to give me money she doesn’t have.

Love is not supposed to revolve around money, but this really bothers me. I am too much of a gentleman to leave her. What can I do to make her see the larger picture? — Gentleman Waiting

Dear Gentleman:
You should assume that what you have now — a sometime-employed fiancée with a focus problem — is probably the best you’re going to get. That’s the larger picture. Many couples get by with one partner supporting the household financially while the other takes care of the home and supplements the income with part-time jobs. Would this arrangement work for you?

If your fiancée has a problem sticking with any one pursuit and soaks up your income with unnecessary purchases or through investing in her own businesses, then you can count on more of the same throughout your life together.

Dear Amy: My two teenage daughters are occasionally asked to baby-sit. On more than one occasion, a family has canceled at the last minute, either because a child is sick or because their plans have changed.

This leaves my daughter with nothing to do; it’s especially frustrating because she may have turned down another baby-sitting job in order to commit to this one.

When my husband and I were the ones hiring the sitter, if we had to cancel at the last minute we still gave the young woman a small token, such as two hours’ pay or a gift card so her evening wasn’t a total loss.

What are your thoughts on this? — Stood-Up Sitter

Dear Stood-up: Any freelance worker deals with the issue of last minute cancellations from time to time, and your daughter should chalk this up to “stuff happens.”

If this happens so often that it is cutting into her business, in the future she could tell all parents when they call for a sitter that she has a policy of charging a fee equal to two hours work for a same-day cancellation.

Your own thoughtfulness in dealing with last-minute cancellations is ideal.

Send questions via e-mail to askamy@tribune.com or write to Ask Amy, Chicago Tribune, TT500, 435 N. Michigan Ave., Chicago, IL 60611.

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