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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

Dear Amy: I'm in my 40s. I have grandchildren, and also my own toddler at home.

I feel very blessed to have had a baby at my age, but something that has eluded me is female friendships.

I live in a rural area, but I know that's not really the problem.

I long to have a trustworthy friend.

My only friend died over two years ago, and since then...Read more

Dear Amy: I am a 67-year-old woman. I have one sibling, my brother “Charles,” who is 60. We live very near each other in a rural area.

Over the years Charles has cut ties with nearly all family members, including his three children. Still, he maintained a cordial relationship with my daughter and me – and especially with my son. They ...Read more

Dear Amy: I was adopted as an infant and found my birth mom when I was in my 30s. She had gotten pregnant in high school and gave birth to me at 17.

We lived in different parts of the country and after I found her, we saw each other once a year for over a decade until she died suddenly last year.

After her death, her brothers and sisters, who...Read more

Dear Amy: My mother recently died, and I’m expecting a relatively substantial inheritance from her (my dad died several years ago).

My younger brother, also not living, has two adult children.

My mother (who was a difficult person) originally told me she intended to halve the inheritance between my brother and me when he was still alive, but...Read more

Dear Amy: I am a single woman in my mid-50s. I never married or had children and like it this way.

I enjoy people, but am a classic introvert who recuperates her energy by being alone.

I enjoy going to museums and restaurants on my own. There is a restaurant/bar right down the street from me that I enjoy going to.

Recently, I went to this ...Read more

Dear Amy: My husband and I, along with a lot of other people our age, have not been able to recover from the pandemic. We are both active 75-year-olds and have been married 55 years.

It seems like everyone’s forgotten that most people over 65 are retired and have no young children. They don’t have jobs and colleagues to return to. They don�...Read more

Dear Amy: After a very difficult divorce and a few years single, I married a wonderful partner last year. He brought his 20-year-old son into the marriage.

Since arriving at my home, the son’s prospects have devolved. He quit college. He lost his job. He now sits in his room all day. When he runs out of funds for nicotine or marijuana, he ...Read more

Dear Amy: Several years back, my sister was in a pretty bad place. She was in her early 30s, still living at home, and didn’t have viable career plans. She desperately wanted to get married and have children, and none of this was working out for her, as she had very little self-confidence.

My mother works for my uncle. She has been quite ...Read more

Dear Amy: My father died 20 years ago after a long battle with alcoholism. At the time, he was separated from my mother and estranged from my younger brother.

I chose to maintain a relationship with him through the last months of his life when he was suffering from liver failure, and I forgave him for the pain he had caused our family.

My ...Read more

Dear Amy: In 1964, I met my wife “Laura” and her infant baby “Beth.” (Laura had gotten pregnant with a married man.)

Laura and I were married, and I adopted Beth when she was 1 year old.

We raised Beth as my biological daughter and never heard a word from her actual biological father. We told Beth about her adoption when she was 8. Her...Read more

Dear Amy: My son “Jack” is 26 years old. Five years ago, he came out to me as gay. While this didn’t fully surprise me, it saddened me. I wanted Jack to have a traditional life. I wanted to have grandchildren.

Despite these feelings, I told him I accepted him.

Jack has lived on his own for the past several years. Recently he told me that...Read more

Dear Amy: I have been walking buddies with a neighbor for the last 12 years. We walk together about once a week.

While I usually enjoy our time, there have been unsettling emotional outbursts from her, either crying or screaming about one thing or another.

She has even yelled at me personally, which was shocking and embarrassing to me, and I ...Read more

Dear Amy: I’m a 57-year-old man.

I was recently diagnosed with stage 4 prostate cancer.

I am obviously not overjoyed, but I am totally accepting of this news. Living with – not dying of – cancer means a few lifestyle changes and the need to be more aware of things.

My cancer is not curable, but it is treatable; similar to many other ...Read more

Dear Amy: A little over a year ago, working with my mother’s doctor, I decided it was in her best interests (she has dementia) to move into assisted living.

With help from my spouse, I was able to maintain her unoccupied house for about a year.

We have other elderly relatives in the neighborhood who kept us posted if anything required ...Read more

Dear Amy: After our teen years, my brother and I became close.

After my mother abruptly left town to be with another man, my brother and I were left to clean up the mess, literally and figuratively.

We worked well together. A year or two later he and his family moved far away. I did my best to keep in touch, but with schedule differences it ...Read more

Dear Amy: For the past 50 years, I have lied that I was in the military and served in Vietnam.

I'm now 71. I want to come clean with my son/family.

I ran away from a bad home life at 13 and lived on the streets. It was horrible. I was beaten up and sexually attacked. I tried to commit suicide twice.

My self-esteem was so low for many years. ...Read more

Dear Amy: My wife and I are divorcing after 23 years of marriage. I am moving out soon.

We have a 21-year-old son.

I talked with him about it, and while he’s angry, he says he understands.

The problem, however, is that my marriage was bad for a very long time, and I fell in love with another woman.

My wife refers to me as an adulterer. ...Read more

Dear Amy: I've been dating my boyfriend for the past year. I brought my pets and we moved in with him this past December. He's an amazing guy – the absolute best!

The issue arises with his house. He owns a three-bedroom house.

Last July his sister and her family moved in with him.

This took the total number of people from two adults, three ...Read more