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Dear Readers: Since announcing my departure from writing this syndicated column, I have heard from scores of people across various platforms, thanking me for more than two decades of offering advice and wishing me well in my “retirement.” I am very touched and grateful for this outpouring of support.

The thing is – I don’t think of ...Read more

Dear Readers: With wedding season upon us, I’m re-running a favorite column from 2021 devoted to wedding mishaps — all sent in by readers.

Perhaps reading about some of the things that can go wrong at a wedding will inspire people to avoid these pitfalls.

And if these incidents can’t be avoided, marrying couples can try to embrace them ...Read more

Dear Readers: To mark my final week writing this column, I’ve fired up the “Ask Amy” Wayback machine and am re-running some memorable Q&As culled from the last 21 years of “Ask Amy.”

Dear Amy: I’m a college student from the suburbs of San Francisco. I’ve been attending college in New York.

My best friend from school is coming to...Read more

Dear Eric: One of my closest friends has a toddler and when we're making plans, she will often ask if she should leave her toddler at home with her husband. Oftentimes when I say yes, I would enjoy just catching up with her, she lets me know that leaving her toddler is not really a viable option.

I feel like I am being a bad friend now when I ...Read more

Dear Readers: To mark my final week writing this column, I’m rerunning some of my most memorable questions and answers. Today I’m sharing a thoughtful update from a reader whose question was first published in 2019. Her update follows the original Q&A.

Dear Amy: About five years ago, I completed a Ph.D. under the guidance of an amazing ...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