Hi, Helaine: For a recent significant birthday, I received a number of gift cards as presents, but I didn't use most of them. They are collecting dust in my wallet. Now that it's the holiday season, a... more

Dear Helaine: My wife has been accepted into law school. It’s a private university -- a fancy, highly ranked one that costs a lot. A lot! I’m in my 40s and she’s in her mid-30s. We have investment sav... more

Dear Helaine: I’m writing with a question about medical expenses in retirement. Over and over, I keep reading something to the effect that “a couple retiring today can expect to spend $250,000 on medi... more

Dear Helaine: My house is in a booming neighborhood in an "it" city. I only have a $50,000 mortgage. The property would appraise for about $300,000. It's a large lot, with a house and detached garage ... more

Hi, Helaine: My parents and their surviving sisters and brothers are getting up in years, so my family began to rotate hosting Thanksgiving among the next generation. This year, I'm up.... more

Dear Helaine: I keep reading from multiple sources that the best advice for investing is to invest in low-cost index funds, like with Vanguard, rather than trying to buy and sell individual shares of ... more

Dear Helaine: I'm a fairly prosperous woman in my early seventies. I'm making my will, and I don't know what to do about my 35-year-old son. He belongs to a tiny religious group I consider to be a cul... more

Dear Helaine: I am one of four cousins who co-own a summer house built by our grandparents, who left it to us in equal shares. For many years, it worked out well. There were weeks we all spent togethe... more

Dear Helaine: My husband and I split expenses 65/35 because he came in to the relationship with far more money and earnings than I did. This worked fine for a long time, but I felt burdened with the h... more

Dear Helaine: I am a 64-year-old woman with two problems that will contribute to my being homeless sometime in the future. In 2003, I began dental implant procedures to replace several teeth. I suffer... more

Hi, Helaine: A few weeks ago, I attended a neighbor's house party. She invited me and a bunch of other gals over for coffee, mimosas, brunch and to view a clothing line a friend of hers is selling. Af... more

Dear Helaine: I'm in my early 30s. Three years ago, I had two job offers. One was close to home and near my friends and family, paying $50,000. The other was on the other side of the country, paying $... more

Dear Helaine: I'm in my late 20s with a good but short credit history. For the past three years, I've been aggressively paying down my student loan, and I expect to have it fully paid off by early nex... more

Dear Helaine: My husband and I are expecting our first child in November. Currently, our only debt includes his vehicle loan, our mortgage and his student loans. We both have healthy salaries and curr... more

Dear Helaine: A friend needed a dress for a formal event, and she borrowed one from me. She returned it with stains. She didn't tell me they were there. I found them myself. The dry cleaner couldn't r... more

Dear Helaine: I'm a 63-year-old corporate executive and was unexpectedly offered an early retirement package as part of a corporate downsizing. The package is OK, but nowhere near enough to carry my w... more

Dear Helaine: Earlier this week, I met one of my gal pals for lunch at a restaurant near my home. As the waiter cleaned the table, a plate slipped and sauce spilled on my friend's dress.... more

Dear Helaine: I am 68. I recently sold my condo, and I am purchasing a new home in a state popular with retirees. The home will cost about $250,000. Should I get a mortgage or pay cash?... more

Hi, Helaine: My boyfriend and I are in our late 50s, and we live together in a house I own, along with his two teenage children from a previous relationship. He would like to sell my house and purchas... more

Dear Helaine: I am a senior widow and have been working with my advisers to leave everything equally in my will. However, I was shocked to learn recently that my younger daughter and her husband told ... more

Dear Helaine: My brother and I are trying to figure out how to support my dad and my stepmom, who only have a small income from Social Security. Her daughter and grandchild live with them, but my step... more

Dear Helaine: Help me decide what I should do. I'm a 53-year-old who had it all but lost everything in the recession beginning 10 years ago. I sold off real estate at a loss, closed my business and tr... more

Dear Helaine: My brother and sister both have kids. I don’t. My mother recently changed her will so that instead of each of us getting a one-third share of her estate when she dies, my siblings receiv... more

Dear Helaine: My father has always been the type of person who lived with the idea of “sticking it to the man” as an undertone to his life. As I was growing up, my parents saved enough money to buy a ... more

Dear Helaine: During the recession, I lost a great, well-paying job. I lived off my savings for a time and took a series of short-term, not-well-paying gigs before training for a new field. I was offe... more

Dear Helaine: I own a single-family home in the Silicon Valley. There's about $1 million equity in it and an annual property tax of $2,000 (thanks to Proposition 13, which limits annual tax increases)... more

Dear Helaine: I want to know what to do with my small but steadily increasing savings. I'm one year into a new career after staying home with a small child while grinding away at school. My husband su... more

Hi, Helaine: I recently sold my house and bought another one. I did a 20% down payment, received a decent interest rate on the mortgage, and still have funds left over from the sale. I don't want them... more