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Ask Amy: How can we help our family member through their transition?
Dear Amy: We have a relative in their mid-20’s who is expected to reveal very soon to family and friends that they have transitioned genders.
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Ask Amy: Girlfriend shares every disagreement on TikTok
Dear Amy: These videos get thousands of views, and some of the comments (mostly very negative ones at my expense) include references to the specific apartment complex where I am currently living.
Ask Amy: I’m seeing red flags after accepting his marriage proposal
Dear Amy: I have some opportunities for business travel that appear "fun" and maybe even "opulent," but he doesn't want me doing the "fun" things if he can't go with me.
Ask Amy: I told a woman that she looks ‘good for 60.’ Where did I go wrong?
Where did you go wrong? Oh, let me count the ways, writes Amy Dickinson.
Ask Amy: Marveling at the absence of common sense
I don’t have a lock on common sense, but I am aware that the lack of it in others keeps this column entertaining, writes Amy Dickinson.
Ask Amy: It’s time that someone stands up to him
You can’t stand up to him if your heart is aching and breaking, and so you will have to train yourself to withstand the consequent separation, writes Amy Dickinson. It might help if you see your own choice as sending a strong message to both your daughter and granddaughter: “I won’t let him control me.”
Ask Amy: I learned details of my wife’s family secrets
They have the right not to discuss this with you, writes Amy Dickinson.
Ask Amy: Niece didn’t stop by to stay hi while in Chicago for Lollapalooza
Dear Amy: To get to this concert, they literally had to drive within a mile from my home – both coming and going. She did not visit or let me know they would be nearby. The only reason I know she attended was by her social media posts.
Ask Amy: Son’s girlfriend doesn’t want us staying with them
Dear Amy: I’m so distraught and hurt. I no longer feel comfortable staying there. Nor do I feel comfortable having her stay at our home or even being around her.
Ask Amy: Niece is having trouble coping
Dear Amy: She has lost her self-confidence and blames herself for any failure or frustration.
Ask Amy: I am shocked by my new daughter-in-law
Dear Amy: Can I confront my daughter? I’m worried about her future and her money. There was no prenup, and I could just scream, “Run!”
Ask Amy: Should I keep offering ‘prayers’ although ultimately it’s an empty phrase to me?
Dear Amy: Every time I write or verbally express "thoughts and prayers," I feel like a fraud. It feels completely empty to me.
Ask Amy: I like to be at the airport with time to spare
Dear Amy: My wife, on the other hand, loves to cut it close.
Ask Amy: What should I give to my new neighbors?
I appreciate your friendly spirit, but I do NOT think it is a good idea to knock on strangers’ doors, even if they are your neighbors, writes Amy Dickinson.
Ask Amy: Family not supportive of trans nephew
Dear Amy: Any advice on how to be supportive without stirring the pot?
Ask Amy: Family struggling after homicide-suicide
Dear Amy: Two years ago, my family experienced the tragedy of a homicide-suicide by a beloved family member.
Ask Amy: My husband has become creatively mean
Dear Amy: He knows this bothers me and continues to poke fun, regardless.
Ask Amy: Is it OK if I write the cards?
If your “love language” is giving gifts (it obviously is), then go ahead and do it, take responsibility for it, and write the cards in your own voice, writes Amy Dickinson.
Ask Amy: A fresh divorce brings on new questions
Dear Amy: To be honest we have no idea why they stayed together as long as they did.
Ask Amy: I thought this was a girls weekend. She’s bringing her husband.
Younger couples sometimes feel the need to do every single thing together (more seasoned couples offer one another more latitude), and I have a theory that “Annie’s” husband might have wheeled his way in, writes Amy Dickinson.