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Amy Dickinson

Columnist | Advice
Ask Amy appears on Mondays, Wednesdays, Fridays and Saturdays.
Recent content from Amy Dickinson

Ask Amy: High school friends face boyfriend tension

Dear Amy: My best friend and I are high school seniors and I strongly dislike her boyfriend. He treats her horribly, tells her “no…

Ask Amy: Boyfriend's social surveillance spells trouble

Dear Amy: I have been dating my boyfriend “William” for 2½ years. We are both divorced with children. William’s ex-wife had a horrible two-year…

Ask Amy: Elderly mother is stressed by daughter's calls

Dear Amy: My mom is nearly 90 and is in great health. She is living with my husband and me — and we all…

Ask Amy: New parents wonder about posting, tagging

Dear Amy: As new parents, my husband and I are concerned about protecting our child’s online privacy. Our friends run the gamut from creating…

Ask Amy: Long-distance dieting buddy expresses concern

Dear Amy: Recently, my friend and I started dieting together. Even though she lives across the country, we talk frequently about the weight we’ve…

Ask Amy: Threatened coach leaves kids in gym

Dear Amy: I am a high school teacher and fifth-grade basketball coach. I was recently coaching a practice when a disgruntled parent walked into…

Ask Amy: Woman ties herself in knots to get guy to tie the knot

Dear Amy: My boyfriend and I have been together for more than seven years. He is a wonderful man who has a good intentions,…

Ask Amy: Retiring couple make touchy choice to relocate

Dear Amy: My husband and I are retired in our mid-60s, in relatively good health and financially independent. Our two adult children, who are…

Ask Amy: Wife's secret phone chats revive old affair

Dear Amy: My wife of many years has been engaging in secret phone conversations with an old boyfriend.She lied to me when I talked…

Ask Amy: Abuse survivor can't handle family contact

Dear Amy: About 16 years ago, I decided to sever all contact with my two brothers. This decision was based on the fact that…

Ask Amy: Drunken video of mom creates problems for kids

Dear Amy: My children are friends with a set of siblings. The kids enjoy spending time together, and their mother has even babysat for…

Ask Amy: Girlfriend wonders about 'stepson' relationship

Dear Amy: I am currently dating/living with my boyfriend of three years. He has a daughter (9 years old) from a previous marriage who…

Ask Amy: Family gets a head start worrying about Thanksgiving

Dear Amy: My boyfriend of two years and I will be hosting Thanksgiving for my family for the first time. I know it's still…

Ask Amy: Religious differences might be relationship red herring

Dear Amy: About three years ago, I met a wonderful guy online. “Jeff” and I have very passionate feelings for each other, as well…

Ask Amy: Breakup creates awkward moments at home

Dear Amy: I just broke things off with my fiancé. I told him I didn’t want to get married and that I didn’t believe…

Ask Amy: Overseas move locks mom into anxious cycle

Dear Amy: Our 23-year-old son will soon move overseas. He’s been working toward a goal of teaching in a country whose culture fascinates him,…

Ask Amy: Elderly caregiving seems like neglect

Dear Amy: My husband’s grandmother “Jenny” is 94 and lives alone. Up until three years ago, her son was her main caregiver. When he…

Ask Amy: Ex-wife tries mightily to reunite with husband

Dear Amy: I was 19 when I married my husband, who was 27 at the time. He was here five months before we started…

Ask Amy: Mom caters to the needs of adult son

Dear Amy: I am 55 and my significant other is 56. We are both divorced and have children from our previous marriages. I have…

Ask Amy: Introvert wonders how to explain herself

Dear Amy: I am an only child who was raised by parents who were approaching 50 when I was born. There were no other…

Ask Amy: My partner and I have a baby boy and live together. We are nearly 40

Dear Amy: My partner and I have a baby boy and live together. We are nearly 40. We sold our homes during the housing…

Ask Amy: Relationship falters through mutual bad behavior

Dear Amy: My girlfriend and I had a falling out last month. She told me that she didn't like the fact that I didn't…

Ask Amy: Parents won't forgive her boyfriend's drunken rant

Dear Amy: I was with a man I loved for almost four years. He is now in recovery, but before that he had multiple…

Ask Amy: Marriage hits the skids with virtual affair

Dear Amy: I have been married to my husband for 10 years. Our marriage has gotten better each year. I consider him a good…

Ask Amy: Celebrity stylist has designs on wedding dress

Dear Amy: I have been mentoring a young woman for about five years at my current company. I was instrumental in hiring her at…

Ask Amy: Facebook creates sticky wicket at office

Dear Amy: I work in an office on a small university campus. There are only eight people in our department, and for the most…

Ask Amy: Cookies brought to potluck don't go down well

Dear Amy: I recently hosted a summer potluck dinner for more than 50 guests.One friend called me three times to ask if I was…

Ask Amy: Girlfriend clashes with boyfriend's gal pal

Dear Amy: I have been dating a guy for about 2½ years. A recurring fight that we have is over one of his friends…

Ask Amy: Mom teaches twin sons wrong lesson on giving

Dear Amy: When my twin sons are invited to a friend’s birthday party, I always purchase two gifts (one from each boy) worth about…

Ask Amy: Boyfriend's mom gives cold shoulder over move-in plans

Ask Amy: My boyfriend and I (23 and 24) have been dating for the past seven months. We recently decided to move in together…

Amy: Distant sisters can't connect

Ask Amy: I have a sister who is much younger than I am. I'm now in my late 30s, she's in her early 20s,…

Ask Amy: Elder care takes social toll on daughter

Ask Amy: I’m a daughter of two parents in severely declining health. I am acting as primary caregiver for both of them. This is…

Ask Amy: Chief cook and bottle washer wants to hang up apron

Dear Amy: I am lucky enough to have my adult bachelor son (in his 30s) live near me. His father and I are in…

Ask Amy: She doesn't need parents' approval to move in with boyfriend

Dear Amy: I am a 30-year-old professional woman who owns her own home, has a stable career and lives a couple states away from…

Ask Amy: Neighbor's morning yardwork blows sleep away

Dear Amy: At what hour on weekend mornings is it reasonable to start running leaf blowers and lawn mowers? We have a neighbor who…

Ask Amy: Woman wants family members to include her guy

Dear Amy: I am a woman who has been divorced for three years, after a very long marriage. While I did instigate the divorce,…

Ask Amy: Dating relationship put to test by contact with ex

Dear Amy: I am gay and have been dating a great guy for a year and a half. We have a hefty age difference…

Ask Amy: Karma punishes by not delivering Mr. Right

Dear Amy: Toward the end of my junior year of college, I met a man who I thought was going to be Mr. Right…

Ask Amy: Young man greets adulthood from the couch

Dear Amy: Our son graduated with honors from a private high school several years ago. He wanted to take a year off before starting…

Ask Amy: Awkward family business leads to passive aggression

Dear Amy: My husband and I got into a business arrangement with his brother and his wife. The dissolution of that business left a…

Ask Amy: In-law tension keeps vacation house off limits

Dear Amy: I’ve been married for 10 years to a wonderful man. I have a loving relationship with his mother. When my sister-in-law was…

Ask Amy: Teen worries about friend in abusive relationship

Dear Amy: I'm in high school. My group of friends is so close that we often joke about being family.We are generally a very…

Ask Amy: Grammy may freak over couple's new identity

Dear Amy: My fiancé and I are marrying soon. We’ve already decided on choosing a new last name together and using our previous surnames…

Ask Amy: Baby brother is high on life – and weed

Dear Amy: I am the proud big sister of my 18-year-old brother, "Baxter."His last day of high school was yesterday, and he is set…

Ask Amy: Young marriage is already on the rocks

Dear Amy: I have been married to my husband for two years and we dated for two years before that. Somehow, he managed to…

Ask Amy: Friend's meals are stretching bounds of hospitality

Dear Amy: I have been “best friends” with a never-married woman for 25 years. She does not like to cook and, consequently, eats poorly.…

Ask Amy: Mother should 'trust but verify' son's sobriety

Dear Amy: I have a 19-year-old son. He is my only child. He has been into drugs and alcohol for more than five years.…

Ask Amy: Man's donation results in multiple dividends

Dear Amy: Twenty years ago, I was a sperm donor. My motivation then was entirely financial; since then, I’ve rarely given it a thought.…

Ask Amy: Agnostic offended by prospect of church ceremony

Dear Amy: I am a 49-year-old man. I was raised conservative Christian, but now I am firmly agnostic and I have no interest in…

Ask Amy: Prosperous elders want friends to help pay

Dear Amy: My husband and I are prosperous senior citizens. We are friends with another prosperous senior couple and often socialize together. He no…

Ask Amy: Child of mentally ill mom feels long-term impact

Dear Amy: How do you tell someone you love that they are ruining your life? My mother has dealt with mental illness, addiction and…

Ask Amy: Cousin says no to visit from across political spectrum

Dear Amy: My grandparents have scheduled a visit. They live in another state. Normally I’d be really excited about this, but they’re bringing my…

Ask Amy: Sister's demands for apologies test relationship

Dear Amy: My sister often shares that she is upset about things I said or did years ago. Her pain is real, but I…

Ask Amy: After a false accusation, aunt now wants to move on

Dear Amy: A while back, an heirloom necklace of mine went missing.The only person to visit me recently had been my adult niece. I…

Ask Amy: Teen worries about friend's cutting

Dear Amy: I have a friend, “Morgan,” who I found out has been cutting herself. Morgan has struggled with depression since she was young.…

Ask Amy: Man wonders why his 'Hollywood hello' goes badly

Dear Amy: I’m a middle-aged, white, gay man living in West Hollywood. I’d like your advice on the proper way to give a friendly…

Ask Amy: Mom wishes she hadn't been witness to a kiss

Dear Amy: My family and I live in a small town in the Midwest.My daughter's friend from high school and college, "Laura," is getting…

Ask Amy: Adult daughter hurt after dad, stepmom read old letters to grandma

Dear Amy: My parents divorced when I was 10. My paternal grandmother was the only constant during that tough time. We wrote each other…

Ask Amy: Wife wonders if e-mail relationship is cheating

Dear Amy: My husband I have been married for three years. We jumped through many hoops in order to be together. I thought we…

Ask Amy: Youth sports league juggles compassion and fee

Dear Amy: I am a volunteer for a youth sports league. I coach a team (that my child is on), and help organize team…

Ask Amy: Parents declare princess-free zone for daughter

Dear Readers: Amy is putting the finishing touches on her new book. Enjoy these “Best Of” columns in her absence.   Dear Amy:…

Ask Amy: Woman returns from vacation pregnant by masseur

Dear Readers: Amy is putting the finishing touches on her new book. Enjoy these “Best Of” columns in her absence.   Dear Amy:…

Ask Amy: Why no one wants to dine with your kids

Dear Readers: Amy is putting the finishing touches on her new book. Enjoy these “Best Of” columns in her absence.   Dear Amy:…

Ask Amy: Son doesn't want to wait until mom dies to read mystery letter

Dear Readers: I’ve stepped away from my column for a week while I put the finishing touches on my new book, which will be…

Ask Amy: Jail time and divorce sever grandparent ties

Dear Amy: My son and daughter-in-law are separated. My son is in county jail awaiting sentencing. His wife has moved on and is in…

Ask Amy: Yoga student wants downward-facing silence in class

Dear Amy: I have been practicing yoga for five years, the past two with one teacher. The lessons are private and, as a result,…

Ask Amy: She wants husband to be more engaged with baby

Dear Amy: I’ve been married for five years to a wonderful, funny and very hardworking man. We have one child, who just turned 1.…

Ask Amy: Man's partner has intimate relationship with another man

Dear Amy: For the past two years I have been in love with a wonderful woman. When we met she explained that she was…

Ask Amy: Seriously ill mother also copes with tough teen

Dear Amy: I've been dealing with epilepsy more than 20 years. Several tests by my neurologist mark me as a good candidate for surgery.…

Ask Amy: Stepdad wants to give tenant the boot

Dear Amy: My wife's daughter, 26, has lived with us for the past five years. She pays rent of $400, including everything. Her boyfriend…

Ask Amy: Friend's dominance is discussed in therapy

Dear Amy: I am a woman in my late 60s who has had a friend for more than 40 years. Many years ago I…

Ask Amy: Adult adoptee is handed birth file. Now what?

Dear Amy: I am 43 years old and was adopted at birth. I had the usual curiosities about my biological parents growing up, but…

Ask Amy: Why are parents of sons in second place?

Dear Amy: Why is it that having male children puts us in second place? I have three sons and get very sad when it…

Ask Amy: Son turns 21 and throws a party for the ages

Dear Amy: My stepson recently turned 21. Because he has friends who are minors, his mother warned him about the responsibilities involving the use…

Ask Amy: Co-worker's emotional affair interferes with perfect marriage

Dear Amy: I thought I had the perfect marriage until I met "Brian" three years ago.I instantly felt a connection and attraction to him.…
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