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Amy Dickinson

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

Ask Amy: Dysfunctional relationship should not progress to marriage

Dear Amy: I have a serious problem with my future wife. She has not been faithful. I overheard her talking to her friend about it.…

Ask Amy: 'Mean girl' at office wants to shed title

Dear Amy: Years ago when I was in my early 30s, I landed a great job with an excellent company. I’ve been very happy here…

Ask Amy: Father fears son has been caught by a "cougar”

Dear Amy: I have a stepson who has been dating and living with a “cougar” since he was 23 years old. He is now 33.…

Ask Amy: Long-lost loves don't quite connect

Dear Amy: A year ago I started a relationship with “Joe.” We were classmates but had not seen each other in 37 years. We fell…

Ask Amy: Parents wonder how to discourage teasing

Dear Amy: My husband and I have a bright, social and engaging 5-year-old daughter. Our problem has to do with how some family members and…

Ask Amy: Bereaved woman clashes with jerk

Dear Amy: My daughter died three years ago at age 35 of pancreatic cancer. Three weeks before her death, my husband and I treated a…

Ask Amy: Teen daughter's empathy deficit worries mom

Dear Amy: My daughter is 17, and is off to college in August. She has managed to alienate herself from her two closest childhood friends…

Ask Amy: Roommate wants advance warning of boyfriend's visits

Dear Amy: I share an apartment with two other women. We are all in our 20s. One spends a lot of time at her boyfriend’s…

Ask Amy: Old friend is back, but his wife isn't very friendly

Dear Amy: A friend whom I have been close to since grade school has just moved back to our home area. We were both excited…

Ask Amy: Teen's abusive relationship terrifies parents

Dear Amy: My 18-year-old daughter was dating a guy for about two years. Although neither her dad nor I approved of the relationship, we kept…

Ask Amy: Wedding season is littered with 'I don't' bombs

Dear Amy: I have been with my boyfriend for seven years. He is an excellent man and I feel lucky to be with him. That…

Ask Amy: Wife sharing a bed with boss is risky business

Dear Amy: My wife occasionally has to travel with her boss overnight to operate technology at meetings. She makes the travel arrangements. I noticed a…

Ask Amy: Her on-off boyfriend and mom are on the outs

Dear Amy: My boyfriend/fiancé and my mother do not get along and it bothers me. He says that because we have had many issues within…

Ask Amy: Parents want daughter's boyfriend to put a ring on it

Dear Amy: My 29-year-old daughter has been seeing her 37-year-old boyfriend (neither has ever been married) for just over one year. They seem to talk…

Ask Amy: Parents want to investigate daughter-in-law for cheating

Dear Amy: My husband and I are aware that our daughter-in-law has been cheating on our son for over a year. The person she is…

Ask Amy: Burned-out worker seeks motivation

Dear Amy: I am a 52-year-old administrative assistant who is burned out. I take full responsibility for not having a career area that I find…

Ask Amy: Dad wants to tell daughter's partner he's a lazy jerk

Dear Amy: My daughter is 32 years old and works long hours as a nurse at our local hospital. She has done well by purchasing…

Ask Amy: Will family tag sale turn into greedy grab fest?

Dear Amy: My husband and I plan to have an estate sale in a month. My wish is to donate the proceeds from the sale…

Ask Amy: Graduate's solo cross-country trip has parent worried

Dear Amy: My 24-year-old daughter just graduated from college after a difficult journey and several false starts. We are very proud of her. This summer…

Ask Amy: Sometimes, the heart should not go on

Dear Amy: Very late in life, after marriage to an executive (now deceased) whose career always came first, I married a wonderful man who loved…

Ask Amy: Meddling woman hijacks friendships

Dear Amy: Some years ago I introduced an acquaintance to my closest friends. At that time I did not know she would do anything to…

Ask Amy: Sometimes 'I love you' seems like a threat

Dear Amy: My husband and I have been married for three years, and I have known his family for five years. I used to get…

Ask Amy: Secret passion leads to awkward friendship

Dear Amy: Almost two years ago, I fell hard for a man who at the time was my professor (he’s seven years older than I).…

Ask Amy: How to help when friends start to fail

Dear Amy: We have old friends who for most of their mar­riage traveled, so­cial­ized, at­tend­ed events and were al­ways look­ing for­ward to some­thing. Late­ly, how­ever,…

Ask Amy: Advice for an advice giver

Dear Amy: I have a really good friend who is having some personal issues. She asks me for help and advice, but she won’t follow…

Amy: Neighbor wonders how to intervene

Dear Amy: I have a neighbor who is usually kind, thoughtful and pleasant. He will go out of his way to help anyone. He presents…

Ask Amy: Mother wants to cut back on visits with Granny

Dear Amy: My mother didn’t like having kids. She never laughed or enjoyed us when we were growing up, and she’s similar in her attitude…

Ask Amy: Inviting co-workers to weddings is risky business

Dear Amy: I am wondering if you have some advice for me regarding a co-worker and my upcoming wedding. There was a time last year…

Ask Amy: Couple don't agree on financial transparency

Dear Amy: My husband and I have been married for seven years. We still have separate bank accounts. I opened one joint account to which…

Ask Amy: Family wonders how to deal with 'complete jerk'

Dear Amy: Our family has a problem. We wonder what to do about the man who in all likelihood will soon be the husband of…

Ask Amy: Do you need to forget in order to forgive?

Dear Amy: I have seven brothers and sisters. One of my brothers waited to get married until his mid-40s. Before marrying, he was happy…

Ask Amy: Is it right to contact the boss over ex's stalking?

Dear Amy: My ex and have been separated for six years. After that we were on and off as a couple, but a year ago…

Ask Amy: Wife's enthusiasm creates burdensome sexpectations

Dear Amy: I am 64; my wife is 62. We are empty nesters. My wife and I are intimate most often on weekends, when I…

Ask Amy: Boyfriend's pricey gifts bother her

Dear Amy: My high school sweetheart has found me after decades apart.He seems to have become very superficial and wants to shower me in high-end…

Ask Amy: Illness interrupts wife's sexual desire

Dear Amy: My wife and I have been married more than 50 years. We are in our 70s. About seven months ago, my wife stopped…

Ask Amy: Parent jealous of new in-laws' togetherness

Dear Amy: One of our children recently married into a large, close-knit, gregarious family. These folks spend all holidays together, vacation together and, although most…

Ask Amy: Widow's solution could be sitting in driveway

Dear Amy: I lost my husband in a motorcycle accident in August 2014. Since then I’ve moved cross-country to be closer to my family and…

Ask Amy: Brother demands apology for religion slight

Dear Amy: A few years ago, my brother asked my husband and me if we would be willing to take in his daughter, as she…

Ask Amy: Family wonders how to respond to abusive partner

Dear Amy: My sister “Nancy” has been in an off-and-on relationship with “Sid” (both are 30 years old) for the past eight years.He is from…

Ask Amy: Granny wants him to put a ring on it

Dear Amy: I have a 23-year-old granddaughter who has been living with a 25-year-old man for over five years. He doesn’t seem to feel he…

Ask Amy: Parents wonder how to discipline other people's kids

Dear Amy: My wife and I are friends with the families of two children who play with our 7-year-old son. We know these families separately…

Ask Amy: Niece wants to confront uncle about family secret

Dear Amy: I grew up in a small town where everyone knows everyone’s business.My grandmother recently told me that the father of her son-in-law is…

Ask Amy: Girlfriend tells 'little' lies – a lot

Dear Amy: I have been dating my girlfriend for nine years. When we met she was going through a divorce and had kids to raise,…

Ask Amy: More on how to handle bullying

Dear Readers: I’ve stepped away from my column for a few days. Please enjoy these “Best Of” columns in my absence.Dear Amy: You asked for…

Ask Amy: Are quips a good 'comeback' to bullies?

Dear Readers: I’ve stepped away from my column for a few days. Please enjoy these “Best Of” columns in my absence.Dear Amy: My 12-year-old son…

Ask Amy: 75-year-old has a timeless problem

Dear Readers: While I’m on a short break, I hope you’ll enjoy this “Best Of” column.Let him down gentlyDear Amy: I am 75 years old…

Ask Amy: Don't embrace co-worker's hugging habit

Dear Readers: While I’m on a short break, I hope you’ll enjoy this “Best Of” column. He’s huggy for herDear Amy: I have been an…

Ask Amy: Nice guy husband can hold his drink. Is that a problem?

Dear Readers: I’ve stepped away from my column for a few days. While I’m gone, I hope you enjoy these “Best Of” columns, culled from…

Ask Amy: Pets dominate our lives, and this column

Dear Readers: I’ve stepped away from my desk for a few days. While I’m gone, please enjoy these “Best Of” questions. Today’s theme is pets.Retrieving…

Ask Amy: Parents wonder how to dole out allowance

Dear Readers: While I’m on a short break, I hope you’ll enjoy this “Best Of” column, which tackles parenting questions.Allowance guidelinesDear Amy: I grew up…

Ask Amy: Series of losses made worse by pal's distance

Dear Amy: Sixteen years ago my best friend introduced me to the man who would become my husband. Her husband, “Stan,” was my (future)…

Amy: Volatile friend lashes out, making others worry

Dear Amy: Our group of friends has been close for a long while. We are all in our early 30s and have been friends more…

Lucky wife and mom faces midlife ennui

Dear Amy: I am a 42-year-old wife and mother who is incredibly grateful for wonderful and healthy children, an incredible husband, good girlfriends and a…

Ask Amy: Family wants to exclude aunt from memorial

Dear Amy: My mother passed away, and my sisters and I are planning her “celebration of life” gathering.Mom was a loving and generous woman…

Ask Amy: Sisters wonder how to confront abusive dad

Dear Amy: My childhood was rough. My mother died when I was 6. She wasn’t around much before that, but it took a hard…

Amy: Wife's grip on the purse strings is abusive

Dear Amy: The company I worked for offered an early retirement package. Since I am not old enough to draw on my pension, I would…

Ask Amy: College freshman tired of baby-sitting drunk roommate

Dear Amy: My freshman college daughter was not in a drinking crowd in high school. Her college roommate and her roommate’s friend party very…

Ask Amy: Mom wants to keep kids' wages minimum

Dear Amy: My twin 13-year-old daughters earn a few extra dollars baby-sitting neighborhood children.After my daughters completed the daylong Red Cross baby-sitting class last…

Ask Amy: Lawyer should charge by the billable whines

Dear Amy: I’m a 29-year-old attorney. My 60-year-old secretary is Eeyore. She is a very nice woman but is also one of the unhappiest…

Ask Amy: Teen's sugar addiction is not so sweet

Dear Amy: I am a young teen who has a bad addiction to sugar. When I have tea, I put way too much sugar in…

Ask Amy: Man wonders if co-worker is gay, wants to contact him

Dear Amy: Many years ago, I had a sexual relationship with a man. After we had been involved for about a year, he told me…

Ask Amy: Family table manners are grossly inadequate

Dear Amy: My husband and I just hosted another family meal and, once again, I am dismayed by the complete lack of basic manners and…

Ask Amy: College grad returns home to a hoarder

Dear Amy: My mother is a hoarder. I have had a tumultuous relationship with her all my life. I recently had to move back in…

Amy: Sex addict not welcome at Thanksgiving

Dear Amy: My42-year-old cousin is in a serious relationship with a 52-year-old man. She recently learned that he told her child’s 23-year-old baby sitter his…

Ask Amy: Man insists on biological child to create family legacy

Dear Amy: My boyfriend and I are in our 50s. We have known each other for 15 years, but started dating two years ago after…

Ask Amy: Anniversary getaway is all business

Dear Amy: I have been planning a four-day weekend getaway with my wife to celebrate our 20th anniversary. We have school-age children and work…

Amy: Drunken party causes fracas

Dear Amy: My boyfriend and I hosted a party. We consumed lots of alcohol. My boyfriend was drunk and started fighting with his friend. He…

Amy: Mother worries about daughter's bi guy

Dear Amy: My almost-25-year-old daughter is in a live-in relationship with a 36-year-old man who professes to be bisexual.He didn’t tell her this in the…

Ask Amy: Dad worries son's life is going to pot

Dear Amy: My 18-year-old son started college this year. He has a part-time job and is paying for a new car to drive to school…

Ask Amy: Woman treats friend like a spare tire

Dear Amy: I’m a woman in my late 20s. For several years, my friend “Terence” has always been there for me. He has…

Ask Amy: Life is perfect, but the toddler must go!

Dear Amy: I recently joined a wonderful family when I married a great man.Everything’s perfect — except for his nephew.The boy is not quite old…

Amy: Woman dreads telling parents she's pregnant

Dear Amy: Recently my husband and I decided we wanted to have another baby. A few days ago we learned that I’m pregnant.The problem is…

Ask Amy: Should optimist stay with depressed partner?

Dear Amy: I’m a single mother of three who has been dating a single father of three, on and off, for just over a year.…

Amy: Worried about addicted daughter's weight gain

Dear Amy: My daughter, 23, had severe alcohol dependency two years ago. She went through rehab and remains sober. She is under the care of…

Teen son's porn habit worries mom

Dear Amy: My 18-year-old son and I were sharing a computer. I stumbled on his activity when he left it open. It was deeply disturbing…
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