Dear Mrs. Riches:
I have a brother, "Dan," who is in his late 30s and still lives with our parents. He has moved out several times over the years but always manages to come back. He is a chronic complainer who has a lot to say about everyone else's incompetence, and I suspect that it's for this reason that he never stays in a job for long. When he lives with our parents, our mother cooks for him and does his laundry; he doesn't pay a speck of rent. My parents are infuriatingly neutral on the subject, saying only things like, "It's nice to have an extra set of eyes on the place now that we're getting older," and, about his repeated job failures, "He is so misunderstood."

I feel a lot of things about this situation -- mad that my brother is taking advantage of our parents, irritated that my folks aren't more judgmental about his flaws, and disgusted that no one but me seems to see anything wrong here. What gives?

--Sick of the Slacker

Dear Sick of the Slacker:
Lots of us have a slacker lurking about somewhere on our family tree: the person who somehow managed to never grow up and separate from dear old Mom and Dad. To their credit, they seldom accomplish perpetual childhood (or even more accurate, petulant teenager) status on their own. Usually, someone well-meaning plays rescuer over and over again.

In your family's case, your Mom and Dad are the classic "enablers" (an overused word I try to avoid, but warranted here), allowing your brother a break from life whenever he mucks up in the real world. While your parents sound like the supportive, understanding types, they have effectively crippled your brother by never forcing him to work through adversity. Why bother working out tough situations on the job when you can go back to Mom and Dad's house and get a personal chef and laundress, all for free?

You know this and I know this. But your parents and brother are either not so enlightened or have just made their own peace with this situation. My guess is the latter: Both your brother and your parents have made a decision to allow this cycle to keep playing out again and again because it meets some hidden need that's not so obvious to you or me. Perhaps an empty nest is hard on your mother and she likes playing the role of caretaker again. Perhaps your brother is really afraid to be out on his own and so he makes up reasons why his jobs just don't work out. We could speculate forever. Like it or not, it is their situation to enable or to confront, as much as it pains you to stand on the sidelines.

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Elizabeth Brokamp, a.k.a. "Mrs. Riches," is a Licensed Professional Counselor who loves to study what happens when money and emotions intersect. She is married to The Motley Fool's own Robert Brokamp, editor of the Rule Your Retirement newsletter. To get your money and relationship questions answered, send her an email. The Fool has a disclosure policy.