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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

Dear Eric: My husband and I just celebrated our first anniversary, and we cutely decided to give each other a gift in keeping with the antiquated anniversary gift themes. The first year is paper or clocks. Smartly and thoughtfully, my husband gifted me a clock made of paper he had seen me looking at in a museum gift shop. But this thing is ...Read more

Dear Readers: Before I leave this space at the end of June, I’m taking advantage of my senioritis and re-running some of my favorite columns.

The following Q&A is an example of a prank question that savvy readers enjoyed so much that it went viral. Honestly, I don’t know how I missed this obvious nod to a beloved sitcom, but I did.

I hope ...Read more

Dear Readers: As I have announced previously, I am leaving this space. My last column will run at the end of June. (Readers can continue to find my work through my newsletter and at amydickinson.com.) In the meantime, I’m publishing some favorite columns and updates on previously published advice. The original Q&A (first published in 2022) is ...Read more

Dear Amy: Two years ago, my friend “Kim” admitted that she has cut alcohol out of her life after her brother died due to his alcoholism.

I thought this was great; we have enjoyed doing things together without alcohol.

A couple of times I suspected she had been drinking.

Last summer I took my suspicions to her sister-in-law, “Bea,” who...Read more

Dear Amy: My 83-year-old widowed mother is depressed, and I don't know how to help.

She refuses to see a therapist and sees drugs as a crutch. She has always been a very private person, is generally distrustful of doctors, and would never let down her shields to a stranger.

I have told her that I am not a therapist, but she has lately begun to...Read more

Dear Amy: Which is the default position regarding asking for help versus offering to help?

For instance, let’s say I’m at work and someone walks past my desk several times, carrying a big box each time.

Assuming that carrying the big box is part of their job, do I stop doing MY job to offer my assistance, just because it is the polite ...Read more

Dear Amy: On this recent Mother’s Day, my 50+ daughter once again asked to bring a new boyfriend to our home for a small family holiday gathering she'd been invited to. We had never met him.

It has been a pattern for her to date someone for only a few weeks, want to bring him to a special family event or holiday, when he is a complete ...Read more

Dear Amy: I am getting married in July at the age of 54. My boyfriend and I have been together for 18 years and have no children. This is our first marriage and we just never saw any reason to get married before, but now due to some plans for our future, we know that being married will be easier for us.

We are having my sister be the officiant ...Read more

Dear Amy: My wife and her sister “Bobbi” have stopped speaking to each other over a disagreement that has now lasted for more than two years.

Our families live on opposite coasts, so communication has always relied on phone/video calls.

During the pandemic, my wife made a particular effort to schedule video calls for our young children ...Read more

Dear Amy: I am a 45-year-old married woman with three children.

I volunteer for a nonprofit organization and through this work I met a nice older woman (58) in this group. “Carol” was very nice, but over the past two years, she's become very attached to me. This makes me uncomfortable.

She messages me over Facebook every morning and every ...Read more

Dear Readers: As I announced last week, my final “Ask Amy” column in this space will run on June 30. (Readers will be able to find me through my newsletter and on amydickinson.com.)

Until then, I’ll occasionally open my files and rerun some previously published Q&A. Here are two:

Dear Amy: I learned that my boyfriend might have cheated ...Read more

Dear Readers: I appreciate it when people give me “updates” on previously published advice.

This update follows the Q&A, which was originally published in 2016.

Dear Amy: I’m hoping for a career in art, specifically as an illustrator.

Three years ago I graduated with an art degree and have been working to make that happen, doing a lot ...Read more

Dear Amy: I am a very active 66-year-old woman. I hate being idle.

My mostly amazing husband doesn’t mind idle time.

This would be OK, except he resents my constant coming and going.

After retiring from a stressful corporate job, I have two part-time jobs; one that takes about eight hours during the week and the other four hours on the ...Read more

Dear Amy: After my spouse of over 40 years died last year. I have moved forward in my life in a positive manner.

I am having a relationship with a married woman (“Brenda”). As a widower, I have found this to be very helpful.

Brenda’s adult son and daughter have supported her in allowing this relationship to continue and grow.

Brenda's ...Read more

Dear Amy: My son "Jeramiah" has been dating "Anabel" for over a year.

Anabel has never brought my husband or me a card or gift for our birthdays or Christmas. She has never offered to help clean up after a meal, even when my son is helping.

I had surgery, and she never asked how it went or how I was feeling.

My biggest concern is her lack of ...Read more

Dear Readers: After 21 years writing the “Ask Amy” column, I’m announcing that I’m leaving this space. My final column will run at the end of June.

I’m healthy, happy, and 64 years old. This is a decision I’ve been wrestling with for more than a year.

When I was first hired by the Chicago Tribune to write an advice column after Ann...Read more

Dear Amy: My husband of 45 years recently came to me with a proposal. He wants to deepen a friendship with a single woman 20 years younger.

He says she lifts his spirits, is creative, and is a great mom to her children.

Their conversations are lively and interesting, and he finds that he wants to be around her more often.

I was flabbergasted...Read more