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Amy Dickinson

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

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: Former friend flees first, worries later

Dear Amy: About five years ago, my (now ex) boyfriend and I leased a place with some friends. One of these friends, “Mark,” ended…

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.…

Ask Amy: Friendship 'freeze-out' after years of insults, childishness

Dear Amy: My husband and I decided to end a 25-year couple friendship after many years of putting up with the wife’s veiled, and…

Ask Amy: Hardworking husband doesn't work on marriage

Dear Amy: For much of our marriage (25-plus years), my husband worked 60-plus hours per week. While I admired his work ethic, it came…

Ask Amy: Abusive father now insists that daughter apologize

Dear Amy: My parents got divorced when I was a toddler. My father was very abusive — verbally and physically — so I did…

Ask Amy: Woman from abusive family finds same with husband

Dear Amy: I’ve been married for almost 20 years to a man who I think is a good person and a good provider. When…

Ask Amy: Husband struggles to navigate tricky family dynamic

Dear Amy: My mother has made my wife's life difficult — with poor comments and decisions, and by not respecting my wife as the…

Ask Amy: Teen son is abandoned by friends; can dad help?

Dear Amy: My 15-year-old son had numerous friends, but in the past year all of them have taken to drinking (vodka) and smoking pot.…

Ask Amy: Mother worries that daughter is a self-absorbed jerk

Dear Amy: I am the mother of 21- and 19-year-old daughters. They are both in very self-absorbed stages — the older more than the…

Ask Amy: Son and girlfriend filched material; what's a mother to do?

Dear Amy: My dear adult son (in his 30s) recently invited me to meet his new girlfriend of two months. He seems to be…

Ask Amy: Getting a Ph.D. was easy, compared with dealing with Mom

Dear Amy: I am a 27-year-old recent Ph.D. graduate who has moved back into my parents' home (hopefully temporarily) and looking for my first…

Ask Amy: Teen girl is ready to have a baby, but is her guy?

Dear Amy: I've been seeing this boy. We've hit it off very well, right from the beginning.We have been dating for six months, and…

Ask Amy: Technological glitch leads to missed connection

Dear Amy: I am one of the blessed millennials who has a job I love. This job happens to involve a great deal of…

Ask Amy: Woman feels betrayed when friend dates her ex

Dear Amy: I broke up with my boyfriend of three years a few months ago.I thought we were working on things and were going…

Ask Amy: Readers respond to an engagement ultimatum

Dear Readers: A recent letter from "Wannabe Fiancee" described a familiar situation. She had lived with her boyfriend for five years, and despite dropping…

Ask Amy: Husband's cancer leads friends to suggest miracle cures

Dear Amy: My husband was diagnosed with stage 4 pancreatic cancer last fall. He has been on chemotherapy, but two regimens have ceased to…

Ask Amy: Gay teen wants to come out in time for prom

Dear Amy: I am 17 years old and a lesbian. I'm trying to figure out how to come out to my family, or at…

Ask Amy: Sisters crush one another by not 'being there'

Dear Amy: I have three sisters. We have no brothers. We are all over 60.In 2013 and 2014, two of my brothers-in-law died and…

Ask Amy: For this student, 'wife me' equals 'beer me'

Dear Amy: I am a college student. I have had one serious boyfriend. We broke up at the beginning of this year, and I…

Ask Amy: Teen daughter wants some dime to pay for ink

Dear Amy: Our daughter is a bright, talented 19-year-old who has already gotten four small tattoos, several ear piercings and a nose ring. You…

Ask Amy: Married man is being blackmailed by former lover

Dear Amy: I'm an older man, married for a number of years. Not a "terrific" marriage, but I've lived it so long I'm just…

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: Single mom struggles with imminent empty nest

Dear Amy: I am a single mother of a 17-year-old son in his last year of high school. He is an only child. I…

Ask Amy: Lonely divorced woman wants to get a life

Dear Amy: I'm a middle-aged woman with no life!I was never a very social person, and my ex-husband wasn't the friendly type (we've been…

She doesn't need to be 'healed'

Dear Amy: I'm in my 30s and use a wheelchair as a result of a congenital disability. I was sitting outside a cafe when…

Ask Amy: Man moves in with his boyfriend, is only offered the 'closet'

Dear Amy: My boyfriend and I (we are gay) have been together for three years.I used to travel for work, and he hated it.…

Ask Amy: Middle-aged man wants his mother to pay for his wedding

Dear Amy: My brother, who is over 45, has become engaged to his boyfriend of four years. They are planning an extravagant wedding and…

Ask Amy: Real woman competes with porn for attention

Dear Amy: I have been dating my boyfriend for almost seven months. We have had our ups and many, many downs, but we are…

Ask Amy: Alcoholic wants family to host no-alcohol events

Dear Amy: I am an alcoholic in remission. I am not recovering — I have a disease that I fight daily. For almost 17…

Ask Amy: Stressed teacher wonders about exiting profession

Dear Amy: I’m a 27-year-old teacher of remedial English at a high-needs urban high school. I’m in my second year, and this job has…

Ask Amy: Adopted teen heartbroken by search for birth mother

Dear Amy: I am a teenager and I am adopted. I was raised knowing that I'm adopted, but not knowing the full identity of…

Ask Amy: Different takes on the unkempt look for men

Dear Readers: I've stepped away from my column while writing my new book, which is scheduled to be published in the fall. Enjoy these…

Ask Amy: Worries about office life

Dear Readers: I have stepped away from my daily column while I work on my next book, a memoir, which is scheduled to be…

Ask Amy: Mother controls couple's social life

Dear Readers: Please enjoy this topical "Best Of" column while I am away writing my next book. Today's topic is about boundaries.Dear Amy:…

Ask Amy: Barista ponders rude customers

Dear readers: I have stepped away from my column for two weeks to finish writing my next book. I hope you'll enjoy these topical…

Ask Amy: Friends, lovers and lots of drama

Dear Readers: I have stepped away from my daily column for two weeks to finish writing my next book, which is due to be…

Ask Amy: Wedding questions

Dear readers: I have stepped away from my column for two weeks to finish writing my next book. I hope you'll enjoy these topical…

Ask Amy: Awkward descriptions

Dear readers: I have stepped away from my column for two weeks to finish writing my next book. I hope you'll enjoy these topical…

Ask Amy: Young love has its ups and downs

Dear Readers: I have stepped away from my daily column for two weeks to finish writing my next book. I hope you'll enjoy these…

Ask Amy: Is this family obligated to celebrate milestone birthday?

Dear Amy: My in-laws are hosting a birthday party for my husband's grandfather. He is turning 90. The party is 200 miles away. My…

Ask Amy: Reader wonders why parents with visitation fade away

Dear Amy: Please help me to understand why it seems so common that after a divorce, the parent with visitation will allow themselves to…

Ask Amy: Grandma worries grandson looks like a granddaughter

Dear Amy: My youngest grandson, "Jamie," is 3 years old. He and his family live out of state, so we only see him two…

Ask Amy: Mom's boyfriend causes strain during visits

Dear Amy: My mother and I have lived halfway across the country from each other for over 20 years. I enjoy spending time with…

Ask Amy: Cousin confab turns into drunken debacle

Dear Amy: During the holidays, our cousins invited my brother, sister and me (along with our spouses and families) to her home for dinner.…

Ask Amy: Woman wonders how to get her guy to help at home

Dear Amy: I recently started a new higher-paying job that I love. I work one 48-hour shift and then pick up extra hours to…

Ask Amy: Parents punish child for reporting unwanted touching

Dear Amy: Recently a 10-year-old reported to me that her friend's daddy had slapped her on her bottom twice and also held her in…

Ask Amy: Childless man learns he might be a dad

Dear Amy: When I was in my late 20s in the 1990s, I dated a woman for several months before I broke it off.A…

Ask Amy: Married woman fantasizes about woman at gym

Dear Amy: I am married to a wonderful man, but recently started obsessing over a woman I see at my gym.I hate myself for…

Ask Amy: He married a single mom and now wants out

Dear Amy: I married a single mom. Now that I am in the thick of it, I want out.I grew up an orphan, so…

Ask Amy: Abused husband wants to win wife back

Dear Amy: My wife and I met when we were 20. We've been married for 15 years. We have two wonderful young children. Our…

Ask Amy: Her lovely daughter is overweight; what's a mom to do?

Dear Amy: My 18-year-old daughter is beautiful and very smart. She is going to her dream college. My concern is that she has gained…

Ask Amy: Artist copes with unsolicited artless advice

Dear Amy: I'm an artist hoping to get a career as an illustrator. I graduated with an art degree three years ago and have…

Ask Amy: Mother struggles with daughter's weight

Dear Amy: My daughter was extremely active in high school. When she went to college, she decided not to play any sports at all.After…
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