Do you have questions about inheritance, tipping, weddings, re-gifting, or any tricky money issues relating to family and friends? Send them to MarketWatch's Moneyist.

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‘All of these tips add up’: If a restaurant adds a 20% tip, am I obliged to pay? Should tipping not be optional? 

'Some restaurants add additional service fees for the benefit of employees,' one reader writes.

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My brother-in-law is being honored by a charity, but tickets for the ceremony cost $375. Should he offer to pay for my ticket?

"My brother-in-law is on the organization's board and was part of the team that set the ticket pricing."

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‘When I ran it past the missus, she went ballistic’: I want to buy a $40,000 car, but my wife said no. Then things really got weird.

"After a decade-plus of driving the automotive equivalent of a plateful of boiled spinach, the new car has captured my imagination."

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‘Her behavior is egregious’: My sister blocked my number. Should I remove her from our $70 family cellphone plan?

'We grew up in a tumultuous household.'

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I’m 46 and a single mother. Should I empty my 401(k) to pay off my house? There’s $128,000 on the mortgage.

‘I currently make good money, and not having to pay a monthly mortgage will help increase my savings.’

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‘I’ve suffered for a long time’: My mother demanded I return my inheritance so she could give it to my brother, who has a drug addiction. What should I have done?

She told me, ‘I can't say no to him.’

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I’m sick and tired of tipping 20% every time I eat out. Is it ever OK to tip less? Or am I a cheapskate? 

‘Over the last 12 months, I have seen my rent go up by 25%. I’m now paying $3,200 for a one-bedroom apartment.’

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‘I married a person who was nothing short of evil’: He has threatened to take my house if we divorce. What can I do?

‘My tenant has not paid a dime since December 2021. He has destroyed the home. He stole my mail, and has been committing credit-card fraud.’

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‘Tipping culture is out of control’: I was asked to tip 15% when I made a donation to charity. When will this madness end?

‘It's not a gratuity anymore, it's become another tax.’

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The cable guy introduced my 90-year-old stepmother to a new ‘friend,’ and she’s gotten fleeced. Am I legally responsible if she ends up destitute?

‘The bad news is she has welcomed this friend back into her home as a live-in caregiver after kicking her out twice.’

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How do we ensure our step-grandchildren don’t inherit our estate? We’re worried our adult children will predecease their spouses.

‘Our son and daughter are parents to biological children as well as stepchildren.’

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‘Poor people are not stupid’: I grew up in poverty, earned $14 an hour, and inherited $150,000. Here’s what I have learned from my windfall.

'When I open my accounts and see how they are growing it really fills me with a sense of pride and determination.'

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I volunteered after 9/11, and was diagnosed with cancer. I received $225,000 from the Victim Compensation Fund. How would you invest it?

‘I am 70, single with no dependents, still working part-time as a freelance writer and editor, collecting Social Security and a pension.’

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‘Am I heartless?’ My husband’s business collapsed and we sold our house. He left home to sell real estate, but failed. Should I bail him out?

‘My kids and I actually felt so much more relaxed and happier since he left.’

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My mother’s will leaves everything to her 3 children. My brother died suddenly — and his wife says she will receive her late husband’s share

'Our spouses are not mentioned in her will and she was not a popular member of our family'

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My son, 34, is getting married. My wife and I want to give him $10,000, but we’re afraid he’ll squander it. What do you suggest?

"We are bitter that he is ungrateful for the support we gave him. He is bitter because he thinks we try to control him with money."

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Should I invest $20,000 in cash or stocks? The stock market is volatile, and the Fed hiked rates (again).

‘My child, who is 4, is back home in school with my parents for now. I’m due to give birth to a second child in July.’

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My husband and I have two children. He has a daughter from a previous marriage. How much should I leave my stepdaughter in my will?

‘Over the years we have helped my stepdaughter and her daughter financially, and we are happy to do so.’

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‘Cry me a river, right?’: I sold our rental for $325,000. I want to invest the money. My wife wants to pay off our mortgage. Who’s right?

‘Why lock up more than $300,000 in the walls of our home?’

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My father retired with up to $10 million, and bought my sister a rehab center. He said no to my request to pay for my kids’ education. What can I do?

‘Two of our children have disabilities, and would really benefit from help with education.’