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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

In a world of instant gratification and constantly wondering “What’s next?” I’m not surprised someone sent this question to me the other day.

In fact, most days I get questions from people asking why a relationship ended when it did and wondering if they could have prevented the time and the heartbreak. Often, the answer is no.

...Read more

Ugly? You have no idea.

Every nasty little private thing a marriage could churn up, every infidelity, every insult and threat, every drunken episode and squandered paycheck, every crying child — there they all were, spilled out from a witness stand in a courtroom.

Then and only then, after wife or husband had exhausted the litany of the ...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 Anna,

I've been in a relationship with my boyfriend for a few months now, and our sex life is generally fantastic. He’s uncircumcised, however, and sometimes sex can be a bit painful. Is it possible his uncircumcised status has anything to do with it? — Puzzled

Dear Puzzled,

Pain and discomfort during sex are never fun, so it’s ...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

In case you don’t know, Bumble is a dating app founded in 2014 by Whitney Wolfe Herd, who was also a co-founder of Tinder. Over the years, it’s been known for its unique approach to online dating, especially with regards to how women interact with potential matches. One of the most distinct features of Bumble is that it requires women to ...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