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'I don't want to squander this opportunity': I sold my business for $130,000. It's the first time in my life I'm not living paycheck to paycheck. What should I do?

'We, his children, do not trust her': My elderly father is recently widowed. His new girlfriend is putting him under pressure to get married. What can we do?

'They think I'm rich because I have a very nice house': My friends order drinks and pricey dishes in restaurants. Is it rude to ask for a separate check?

My mom, 91, has a $5 million portfolio, but leaves her passwords lying around the house. Could a nefarious caregiver steal her money?

My sister inherited $350,000 from her father's estate, but her husband was diagnosed with dementia. Should they divorce so he can qualify for Medicaid?

Live Breaking News & Updates on Dear Quentin

'I don't want to squander this opportunity': I sold my business for $130,000. It's the first time in my life I'm not living paycheck to paycheck. What should I do?

'We, his children, do not trust her': My elderly father is recently widowed. His new girlfriend is putting him under pressure to get married. What can we do?

'They think I'm rich because I have a very nice house': My friends order drinks and pricey dishes in restaurants. Is it rude to ask for a separate check?

My mom, 91, has a $5 million portfolio, but leaves her passwords lying around the house. Could a nefarious caregiver steal her money?

My sister inherited $350,000 from her father's estate, but her husband was diagnosed with dementia. Should they divorce so he can qualify for Medicaid?