The Moneyist: ‘I just don’t care for my stepdaughter.’ I want to give my two kids $100K a year. Would it be wrong to leave my stepdaughter out?

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Dear Moneyist, 

I married a woman 30 years ago. She was a divorcée with a six-year-old child. She divorced me about 10 years ago. (We were married 20 years.) I raised her daughter by providing clothing, food, shelter, braces and college, because her biological dad was a deadbeat loser, and still is.

I had two more children with my wife. I’m in the 1%. Currently, I give all three children equal gifts of $10,000 per year. I never really cared for my stepdaughter and, to this day, I find her personality abrasive. But I remembered very well when my father died. His will heavily favored my oldest sister.

The Moneyist: My mom asked for a divorce. My dad made his mother his pension beneficiary — and then he killed himself. Now my mom and grandma are feuding. Who’s right?

I came from a family of eight children. My father’s last will and testament caused havoc and distrust between us siblings and broke some of us apart. I don’t think my father had any idea of the destruction that he would leave behind. I don’t want my two children fighting with their half sister.

But I really have to work up my inner strength to gift her equally. I want to distribute $100,000 each per child every year. I can easily afford it, but I just don’t care for my stepdaughter. Half the time, I feel like she befriends me just so she can get a payout. I want to do the right thing, but it’s hard.

So I’m reaching out to you for advice and ideas.

Mr. Not-So-Perfect Parent

Dear Mr. Not-So-Perfect Parent,

Like a store full of Waterford Crystal, I want to get in and out of this world without breaking anything.

You fed and clothed your stepdaughter, and read her nighttime stories. You saw her graduate from high school. You watched her mature into a woman. You listened to her problems, and probably gave her boyfriends the once over when they called to your home. You took deep breaths when you lost patience with her, and you felt joy when she came home with news that she made the debate team or when she happily waved the results of a school exam that she had dreaded but worked hard for.

The Moneyist: My father left everything to my son. When I called the attorney about the will, my son got very upset. I now need financial help. Should I ask him for money?

From the age of six, she knew you as her de-facto dad. She could have the same eyes or smile (or temper) as the woman you fell in love with. When you and your ex-wife married, you promised to raise her daughter together. Whether you wanted it or not, you were the father figure she saw across the breakfast table. You were a constant in her life. You led by example. “Mr. Not-So-Perfect Parent” tells me all I need to know. You were her parent then and, yes, you remainher parent now.

The Moneyist: ‘He owed a lot of back taxes.’ My ex-husband forgot to split a $100,000 investment account — then he died. Can his estate come after me for the money?

Given that your relationship was not perfect — who has a perfect relationship with their parents? — it can’t have been easy for you raising your wife’s child, especially if you didn’t feel as close to her as your did with your biological children. There was a distance between you two that you couldn’t quite put your finger on, or maybe neither of you fully knew how you felt about the other. She was both an imperfect stepdaughter and an imperfect daughter. You had the best of both worlds.

The Moneyist: ‘What did he do with all the money?’ My dying husband cashed his $700K life insurance and emptied his bank accounts

She may not have always felt on an equal footing with her siblings. She loved you sometimes. She resented you other times. She wished her own father could have been a parent to her. When and how was the trust lost between you? She doesn’t know. Why didn’t you give her that same warm, wry smile across the dinner table that she believes — rightly or wrongly — that you reserved for your other children? Why you don’t look at her that way even now? Once upon a time, you did.

The Moneyist: My stepfather and mother pooled resources to buy a home. My mom died in 2003 and he just passed away. His kids are selling their house — am I entitled to anything?

If you give two of your children $100,000 a year or $1,000 a year or even $100 a year, and you pointedly leave your stepdaughter out, I believe you risk causing her irrevocable, incalculable damage. If you believe she is abrasive after including her in this annual gift with your two biological children, you will still have done the right thing. If it builds and/or restores trust in your father/daughter relationship, all the better. The worst thing you could do is make this relationship transactional.

Leave that Waterford Crystal intact, and make sure your daughter always knows that she belongs.

The Moneyist: My father-in-law’s business went south and my mother-in-law has never worked a day in her life. How can I avoid supporting them?

Do you have questions about inheritance, tipping, weddings, family feuds, friends or any tricky issues relating to manners and money? Send them to MarketWatch’s Moneyist and please include the state where you live (no full names will be used).

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Hello there, MarketWatchers. Check out the Moneyist private Facebook FB, +1.72%  group where we look for answers to life’s thorniest money issues. Readers write in to me with all sorts of dilemmas: inheritance, wills, divorce, tipping, gifting. I often talk to lawyers, accountants, financial advisers and other experts, in addition to offering my own thoughts. I receive more letters than I could ever answer, so I’ll be bringing all of that guidance — including some you might not see in these columns — to this group. Post your questions, tell me what you want to know more about, or weigh in on the latest Moneyist columns.

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