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Amy Dickinson

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

Ask Amy: Woman should leave troubled relationship

Dear Amy: My boyfriend and I have been together for two years. He has a beautiful daughter whom I have a great relationship with.…

Ask Amy: Views about adoption raise unkind assumptions

Dear Amy: I was adopted at 5 months old, in 1947. I never knew my birth parents. When my children were small, I tried…

Ask Amy: Worker tries to cope with bullying boss

Dear Amy: I have been in my current job for just over two years. I like the work and most of the people I…

Ask Amy: Unhealthy nutrition early in life might mean problems later

Dear Amy: I have two grandsons, ages 1 and 3. My daughter, who is slightly overweight, feeds them foods high in sugar (doughnuts, pancakes…

Ask Amy: Wife of elected official feels the burn

Dear Amy: My husband of 40-plus years, "Paul," is an elected official in our city. Paul is also involved in politics on the state…

Ask Amy: Tips to overcome inertia in your life

Dear Amy: How do you help a lazy person to become more healthily active when the lazy person is yourself? I’ve dealt with depression…

Ask Amy: Woman's weight suddenly bothers sick friend

Dear Amy: I am a woman who is worried about a close male friend who I have known for more than 10 years.We have been…

Ask Amy: Early abuse strains adult relationships

Dear Amy: I was molested (many times) when I was a child by my mother’s father. He told me not to tell anyone because…

Ask Amy: Parents bemoan daughter's Bridezilla transformation

Dear Amy: Our 25-year-old daughter was a strong, compassionate, emphatic, loving person until her upcoming wedding turned her into a self-centered brat. We gladly…

Ask Amy: Husband's friend knew about affair but didn't tell her

Dear Amy: My husband recently confessed to me that he was unfaithful four years ago. We had a great life, or so I thought.…

Ask Amy: Long-ago sexual assault haunts friendship

Dear Amy: My husband and I have been friends with another couple for 40 years. We get together socially, vacation together, visit each other’s…

Ask Amy: Older couple face commuter marriage

Dear Amy: I never thought I would be writing to you. My wife and I are in our 80s, married for more than 30…

Ask Amy: Does shared custody require honest sharing?

Dear Amy: I have a 4-year-old daughter. Her father and I separated when she was a baby. We share custody. He has a long…

Ask Amy: They're moving in together, but do they like each other?

Dear Amy: I've been with my girlfriend for two years and we plan on moving in together in the next few months. We are…

Ask Amy: Wife uncovers truth behind family bequest

Dear Amy: I’ve been happily married to a wonderful man for the past four years. My husband has a teenage son from his previous…

Ask Amy: Aunt, uncle worry about niece's abusive relationship

Dear Amy: Our 25-year-old niece was born with severe hearing loss. She grew up in near-poverty, her father left when she was a toddler,…

Ask Amy: This gentleman prefers womenswear

Dear Amy: I’ve been divorced for several years. I have dated a few gals, but nothing serious, until recently. For about the past 20…

Ask Amy: Mom's alone, and the kids don't come around

Dear Amy: I have three grown children. I feel we have a good relationship, and when we are together we seem to have fun.My…

Ask Amy: Daughter wonders how to disclose alcoholism

Dear Amy: My mom died several years ago, and my father has remarried. The woman he married is an alcoholic. Dad seems to be…

Ask Amy: Man at the beach gives bikinis a round of applause

Dear Amy: My wife and I love the beach. We walk on the beach, kayak, picnic, and in the summer we swim. When it’s…

Ask Amy: No joke: Daughter wants to quit IT job for comedy

Dear Amy: My 27-year-old daughter, "Zoey," was just laid off from her IT job Out West and would like to pursue her long-cherished dream…

Ask Amy: Grandmother wonders if she is obligated to babysit

Dear Amy: I am a 67-year-old divorced, single woman. I live about 10 minutes from my daughter and babysit for my 18-month-old granddaughter two…

Ask Amy: Exhausted mother deserves husband's support

Dear Amy: I am the mother of a 2-year-old and a 5-month-old. My husband and I are both professionals, and I am currently on…

Ask Amy: Dating relationship ends in slander

Dear Amy: I’ve been dating a woman for about six months. We started dating soon after what I thought was the breakup with her…

Ask Amy: Longtime boyfriend worries about infidelity

Dear Amy: My girlfriend and I have been seriously dating for almost nine years. She has a son whom I have helped to raise.…

Ask Amy: Checked-out husband now wants out

Dear Amy: I am married to a beautiful woman who is pregnant with our second child. Over eight years of marriage, our ability to…

Ask Amy: Over a decade later, thank yous still wait

Dear Amy: Eleven years ago, I married the most perfect person for me. We had a very small wedding with just our closest family…

Ask Amy: Photo of deceased friend lives on, on Facebook

Dear Amy: My dearest friend suddenly passed away from a heart attack. His funeral was yesterday. His younger cousin took pictures of my friend…

Amy: Widow wants connection for son

Dear Amy: My husband died when my son was a preschooler. I have been trying for years to get his family to spend time with…

Ask Amy: Homebodies have honeymoon forced upon them

Dear Amy: I got married last year. I saved up and paid for the wedding myself. My husband and I decided not to have…

Ask Amy: Girlfriend enlists guy in dangerous deception

Dear Amy: I am in my late 20s and have been seeing my girlfriend, “Tami,” for more than three years. We have been long-distance…

Ask Amy: Violent ex threatens current relationship

Dear Amy: I have been dating a divorced gentleman for almost two years. He has dated in the past, but as soon as he…

Ask Amy: Dads respond, recommending fatherhood

Dear Amy: You asked for men to respond to the letter from a reader who was wondering if the time would ever be right…

Ask Amy: Wife has trust issues after husband deleted photo from work 'event'

Dear Amy: Three days ago, when I asked my husband if I could see a video he shot on his phone, his face went…

Ask Amy: Jealous guy has girlfriend rattled

Dear Amy: I am a 26-year-old woman who bartends and is starting a career in real estate. I have been dating my boyfriend for…

Ask Amy: Family member wants to reconcile with addict

Dear Amy: My cousin's daughter, who has always been like a niece to me, became addicted to prescription medication two years ago.While addicted, she…

Ask Amy: Daughter wonders what's behind 'advance' inheritance

Dear Amy: My father remarried 14 years ago. He married a Russian woman 15 years younger than he, and bought a house. He paid…

Ask Amy: Wife does too much and receives too little

Dear Amy: I have been married for 33 years. I love my husband, but I have totally enabled him — to the point where…

Ask Amy: Cynical mom not supporting engagement

Dear Amy: My boyfriend and I got engaged a few months ago. It should be the happiest time of my life, but my future…

Ask Amy: Parents worry about son in abusive marriage

Dear Amy: Our son married a girl who is emotionally abusive. She has one child from a previous relationship and they have a child…

Ask Amy: Single mom in a bind about son's slumber party

Dear Amy: I’m a single mom to a wonderful boy who will be 10 next month. His father has very limited involvement, and only…

Ask Amy: Sisters disagree over death disclosure

Dear Amy: My sister and I cannot agree on whether to tell my 96-year-old aunt that my 92-year-old father (her brother) passed away. Our…

Ask Amy: Estranged dad lords over family relationships

Dear Amy: I am estranged from my father. This came about after I confronted him about his molesting and physically abusing my sister and…

Ask Amy: Advice columnists have problems, too

Dear Readers: I’m about to celebrate another anniversary of writing this column, and — after almost 14 years — I will admit that I…

Ask Amy: Leave kids with distracted, pill-losing grandparents?

Dear Amy: My husband and I, along with our two children (ages 3 and 5), will be headed to Florida for a week this…

Ask Amy: She wants a baby, but he has reservations

Dear Amy: My husband and I got married five months ago. We’ve been together for over seven years. He’s in his mid-40s; I’m in…

Ask Amy: Transgender man's pregnancy roils family members

Dear Amy: I’m a proud mother to my gay son. We love him unconditionally. My son married his partner, “John.” They have been together…

Ask Amy: She's worried about 'inflamed hormones' of teens

Dear Amy: We know a couple with a 14-year-old daughter and a 5-year-old son who just took an 18-year-old boy (whom they have known…

Ask Amy: Should toxic mom help daughter deliver new baby?

Dear Amy: My mother and I have had a tumultuous and toxic relationship ever since I was a child. It was a mess of…

Ask Amy: Atheist parents grieve daughter's turn toward religion

Dear Amy: My husband and I raised two great kids. Our son is 30 and our daughter 28. Both of them finished college and…

Ask Amy: Villa guest confronts illegal drug use

Dear Amy: This past summer, my best friend of more than 30 years, her 9-year-old daughter, her new husband and others rented a villa…

Ask Amy: Should she tell 'Mr. OK' about long-ago abortion?

Dear Amy: For the first time in many years, I have been thinking about an episode from my earlier life. I got pregnant one…

Ask Amy: Insulting in-laws' weighty remarks are not welcome

Dear Amy: My in-laws always seem to feel the need to comment on people’s weight, either right to their faces or gossiping about it…

Ask Amy: Atheist should consider becoming 'Goshfather'

Dear Amy: I am a happily married man with two wonderful children. Recently, a close friend and his wife (who are Catholic) asked me…

Ask Amy: Child's flying phobia has family staying home

Dear Amy: My husband and I have two boys, ages 7 and 4. The 7-year-old is a great traveler, but the last time we…

Ask Amy: She was abused by her grandfather, now wants inheritance to pay for therapy

Dear Amy: I am a 23-year-old female. Recently, my grandfather (my mother’s father) died. He and I were estranged due to his ongoing molestation…

Ask Amy: Groom ponders bridal shower etiquette

Dear Amy: I am a groom-to-be. My fiancée and I grew up eight hours away from each other. My mother and my fiancée are…

Ask Amy: Family group wonders how to split cabin cost

Dear Amy: My three siblings and I are planning a getaway for our parents’ 50th wedding anniversary. We have all agreed to split their…

Ask Amy: Daughter juggles relationship with two mothers

Dear Amy: I am a 37-year-old woman who was adopted at the age of 6. My adoptive mother, “Jane,” encouraged me to find my…

Ask Amy: Companionship didn't accompany ride to church

Dear Amy: After a heavy snowfall, I offered a neighbor a ride to church. He gratefully accepted. Once in church, I noticed that he…

Ask Amy: Daughter might not invite mom to her wedding

Dear Amy: My mother and I have a difficult relationship. She has some serious mental issues. She’s seen a few psychologists, but once the…

Ask Amy: Woman in relationship competes with 'sugar mama'

Dear Amy: We first met when I was 14 and he was 16, but when we reconnected we were both married to other people,…

Ask Amy: Constant cousin comparisons causing damage

Dear Amy: My daughter, “Ally,” and my husband’s sister’s children, “Abe and Gretchen,” are all teenagers. While my family relocated away from our Midwestern…

Ask Amy: Widow finds out husband was cheating

Dear Amy: My husband passed away about two months ago. While going through his desk after his death I discovered he was having an…

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: 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: 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: 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: 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: 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)…

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…

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…
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