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Dear Anna,

I’m a 29-year-old queer, nonbinary femme. I’m a pretty quiet and introverted person, so making friends has never been easy for me. Right now, I only have two close friends, and although that might sound sad, I value these friendships deeply because they’re all I have.

Here’s my dilemma: My friends misgender me and ...Read more

Dear Readers: Today I hope you will enjoy a rerun of two of the most infuriating questions I have ever published (slightly edited for space).

Dear Amy: I recently discovered that my son, who is 17, is a homosexual. We are part of a church group and I fear that if people in that group find out they will make fun of me for having a gay child.

He...Read more

Dear Readers: To mark my final week writing this column, I’m re-running some memorable Q&As.

Dear Amy: I am in the most loving relationship with the man I want to marry. We talk about marriage often.

He knows nearly everything about me. The last thing – the thing he doesn’t know – is my protected secret.

Seven years ago, I was raped...Read more

Dear Readers: To mark my last week of publishing “Ask Amy,” I’ve fired up the Ask Amy Wayback machine, and will run some favorite previously published Q&As.

Following is my very first column, published in July 2003.

Dear Amy: I have a major problem that has come up just before my Wedding in Chicago. Children. Don’t want them at the ...Read more

Dear Amy: I have a thoughtful, successful 38-year-old stepdaughter. We have a good relationship and enjoy each other’s company. I live abroad, so I only see her and her family once or twice a year.

The issue I am having is with her husband, my son-in-law.

He is completely anti-social and barely acknowledges my presence.

He has never ...Read more

Dear Readers: The following Q&A first ran in 2020.

Dear Amy: A couple of years ago, an acquaintance of ours hosted a dinner party. I was only acquainted with half the people there. The hostess didn’t make introductions.

One person present was someone I had met a few times. (I’ll call her “Jane.”)

I knew that Jane had a partner, “...Read more

Dear Amy: Several years ago, I was involved in projects with a female friend (I’m a man).

I occasionally made jokes and said things that in retrospect I realize were inappropriate. She finally set me straight.

Then Covid and the MeToo movement hit, and I had time to revisit a number of things that at the time I felt were innocent remarks or ...Read more

Dear Amy: I'm having a hard time letting go of being snubbed by a close friend of many years.

My friendship with “Shelley” included our spouses and children.

We've celebrated, laughed, shared meals, vacations, worries and mourned together.

Recently I learned from a mutual friend that we both were excluded from two major celebrations ...Read more

Dear Amy: I am a man in my mid-60’s, married for the past 35 years to my second wife.

We have two children, both grown and on their own.

We have been sleeping in separate bedrooms for years. She is an alcoholic and is often very nasty toward me. Life is miserable.

Prior to this marriage, I was married for two years to my childhood ...Read more

Dear Amy: My husband and I have a son who is 18-months-old. He seems on track for all of the developmental milestones.

He goes to daycare three days a week.

The children are separated according to age. The place came highly recommended by other parents in our neighborhood, and we’ve been happy with the quality of care.

Last week, one of the...Read more

Dear Readers: In advance to my departure from this column, I’m spending the next couple of weeks rerunning some favorites.

I don’t really have any way of “fool-proofing” the queries sent in to me, and so I’ve treated most of them as if they are serious – or at least genuine.

But sometimes, I’m the fool, and here is proof:

In ...Read more

Dear Amy: My wonderful husband died unexpectedly seven years ago.

I'm now 49, and still have no desire to meet anyone or go on dates.

My husband was my everything and, while I don't want to spend the rest of my life alone, the prospect of dealing with dating and all the hassle that goes along with it makes me wonder if solitude is really that ...Read more

Dear Readers: Before I leave at the end of the month, I’m going through my files and choosing some of my favorite “vintage” columns from over the years. The following Q&A are both from 2020.

Dear Amy: This is a “trivial” subject that has nonetheless bothered me for years.

My parents have the original Trivial Pursuit game, circa 1983....Read more

Dear Amy: I recently discovered that my husband was messaging and talking to three women through the dating portion of Facebook.

I saw messages on his phone from one woman. I also noted that he had a phone call with her that lasted for 44 minutes.

I confronted him about this and he said he was trying to learn how to communicate – and that he...Read more

Dear Amy: My parents were absentee grandparents, despite my longing for more.

For many years and on several occasions, I tearfully asked my mother why they ultimately favored my sibling’s children over my own.

We all live in the same town.

The answer I got implied that my folks had provided some financial assistance to my sibling at some ...Read more

Dear Readers: Over my 21 years writing this column, I’ve stayed in touch with many readers whose questions have particularly affected me.

One such reader, whose question first ran in 2021, provided an “update,” published in 2023.

He and I have continued to correspond, and I’m happy to share an update to his update, as a reminder – ...Read more

Dear Amy: My husband and I bought a house seven years ago. It has a finished basement. The basement has a bathroom, a bedroom, and a den in it.

Our daughter and son-in-law live with us in the downstairs den and bedroom (they use that bathroom). They are employed.

Our daughter is a college graduate and has been married to our son-in-law for 12...Read more

Dear Amy: Just before the pandemic, I started dating a charming, smart, handsome, funny professional guy (we’re both men). Our dates were delightful, except that whenever I suggested getting physically affectionate, he always had an excuse not to.

The relationship faded out. After a few months, I drunkenly texted him and he responded by ...Read more

Dear Amy: My aunt has fallen on hard financial times and has begun leaning on me. Although she has a daughter, two stepsons, a nephew, and the biological father of the granddaughter she is raising, I’m the only one willing to help.

Others are quite able but unwilling due to choosing not to work, refusing to pay child support, or falling out ...Read more

Dear Amy: Forty-two years ago, my uncle died by suicide. I was very young at the time, and for years was told that he died in a car crash.

It was only by accident that I discovered that he had taken his own life. He had a troubled life. It seems he never really felt at home in the world. When he was a teenager, the father with whom he already ...Read more