Amy Dickinson joined Chicago Tribune in July 2003 as the newspaper's signature general advice columnist. “Ask Amy” appears in ...

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Amy Dickinson

Amy Dickinson

Ask Amy

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Ask Amy: Father-son estrangement needs a hero to heal

Ask Amy: Father-son estrangement needs a hero to heal

October 22, 2014

Dear Amy: My grown son (32) has chosen to not speak to me for the past five years. We live in the same town.

  • Ask Amy: Parents worry about addicted daughter's weight gain

    October 21, 2014

    Dear Amy: My adult daughter, 23, suffered a bout of severe alcohol dependency two years ago. She went through rehab successfully, and today she remains sober.

  • Ask Amy: Dating couple ponder part-time parenting

    October 20, 2014

    Dear Amy: My boyfriend and I have been dating for 31/2 years. When he was 20 his casual girlfriend became pregnant and had a baby. His daughter is now 7, but the child's mother is controlling and wouldn't let my boyfriend see his daughter alone.

  • Ask Amy: Sister balks at spending money on dough

    October 19, 2014

    Dear Amy: My sister asked me to purchase a frozen cheesecake, cookies or pretzel dough from my nephew for his school fundraiser.

  • Ask Amy: Wife's rages worry husband and child

    October 18, 2014

    Dear Amy: My wife of 11 years started transitioning into menopause a few months ago.

  • Ask Amy: Woman wants to leap into blended family

    October 17, 2014

    Dear Amy: I have been dating a father of three children for about six months now. I love him and his children, and I am moving in with him this month. I really want to be involved in his children's lives and have us become a family. I get along with his kids, and I feel like they have accepted me.

  • Ask Amy: Husband plays games; marriage is the loser

    October 16, 2014

    Dear Amy: Recently I got a phone call from a local video game store advising me that my husband had won a new game console from a store contest.

  • Ask Amy: Wife says husband can have a girlfriend. Why?

    October 14, 2014

    Dear Amy: My wife and I have been happily married for over 20 years. We raised two terrific sons. We get along great and laugh a lot, but over time her interests have evolved. We used to play sports, but now she goes exclusively to the gym. At home she watches TV several hours a day, including football all weekend. She constantly has her laptop on and has a smartphone in her hand while watching TV (I'm fairly certain she has obsessive-compulsive disorder).

  • Ask Amy: Family rift has deep roots; mom wants closure

    October 14, 2014

    Dear Amy: The last time I spoke to my adult daughter was five years ago.

  • Ask Amy: Sibling rivalry over who can contribute less

    October 13, 2014

    Dear Amy: I graduated from college in May and moved back home. My dad hasn't been working, and my older sister — who lived at home rent-free for three years — has started to pay for our home phone bill.

  • Ask Amy: Uncle wants to be sugar daddy for college student

    October 12, 2014

    Dear Amy: I started college this year. For a gift, my uncle wants to set up an account for me at his credit union and give me a debit card. He wants to reward me for working hard and wants to give me the flexibility to have some fun in college.

  • Ask Amy: Cousin or brother? Siblings search for answers

    October 11, 2014

    Dear Amy: My father had several affairs, left our family and remarried another woman. We have confronted him about his sins, but he acts as though he has done nothing wrong.

  • Ask Amy: Should kids amuse themselves with tech during adult events?

    October 10, 2014

    Dear Amy: Scenario: Grandsons, 7 and 5, at a restaurant or a party with no other children to talk to and nowhere for them to play.

  • Ask Amy: It's time to live your 'second life'

    October 9, 2014

    Dear Amy: As I've entered my later golden years, I often think about mistakes I've made during my life — people I've wronged, people who have wronged me, poor financial decisions I've made, things I should have done (but didn't) and things I shouldn't have done but did.

  • Ask Amy: Soccer mom deplores abusive sideline "coaching"

    October 8, 2014

    Dear Amy: I am a proud soccer mom of two children. My husband coaches their teams. I love watching my children play and my husband coach.

  • Ask Amy: Partner and parent feels like punching bag

    October 7, 2014

    Dear Amy: I'm the punching bag in a relationship with my common-law spouse. We have three children (ages 4, 2, and a baby).

  • Ask Amy: Teen worries that parents' fighting is not healthy

    October 6, 2014

    Dear Amy: I am 15 years old. My mom and dad have always fought a little bit, but recently it has gotten really bad.

  • Ask Amy: Brother balks at bridal honor

    October 5, 2014

    Dear Amy: In three months, my sister is getting married (for the first time). She is 40 (I am 33), has waited her entire life to meet a great man and seems to believe she has done so.

  • Ask Amy: Sexual harassment claim throws bombshell into marriage

    October 4, 2014

    Dear Amy: I have been married for over 20 years to my husband, who is a university professor. Recently he has been accused of sexual harassment by a graduate student, who lives in another city.

  • Ask Amy: Job applicant has audacity of hope

    October 3, 2014

    Dear Amy: I was recently fired from my job for chronic tardiness. I've worked at this business for four years, and though I knew my lateness was seen as a problem by my boss, it was still a surprise to be fired.

  • Ask Amy: Remarriage brings out bad feelings

    October 2, 2014

    Dear Amy: I was recently married to a wonderful man. This is a second marriage for both of us. Our first marriages were difficult and lasted more than 20 years.

  • Ask Amy: All kids need to know the 'facts of life'

    October 1, 2014

    Dear Amy: What is the right age to tell a girl about her period and the "facts of life"?

  • Ask Amy: College student's behavior is soooo high school

    September 30, 2014

    Dear Amy: My first week in college I met "Christy" and "Ally," who were friends in high school. They have rooms next to each other in our dorm.

  • Ask Amy: Teen's hospital tantrum sickens grandparents

    September 29, 2014

    Dear Amy: My 87-year-old husband suffered a life-threatening medical problem. Two of our granddaughters — ages 22 and 17 — visited his hospital room. When he inquired about the 17-year-old's school performance, she melted down — crying and yelling, "You always put pressure on me!" — and ran from his room.

  • Ask Amy: Vacation expense question should be asked outright

    September 28, 2014

    Dear Amy: Next month I am going on vacation with a friend and we are staying at my family's vacation home. Since there will be no hotel expenses and many of our meals will be supplied by my family, I am wondering if it would be appropriate for me to expect my friend to pick up the expense of the rental car.

  • Ask Amy: Sleepy student's girlfriend a nightmare

    September 27, 2014

    Dear Amy: I am at university and value my sleep. Along with caffeine, sleep helps me get through the day. I find sleep relaxing, pleasurable, and frankly, a human necessity.

  • Ask Amy: Grandmother frets about questions following divorce

    September 26, 2014

    Dear Amy: I am 65; my husband is 67. We have been married for 13 years. Now we are divorcing. He will be leaving our state after the divorce, when he retires, and won't be returning.

  • Ask Amy: Neighbor needs to childproof her driveway

    September 25, 2014

    Dear Amy: My husband and I have three teenage boys. We have lived in our upper-middle-class suburban neighborhood for 20 years.

  • Ask Amy: Marijuana use a dealbreaker for this former toker

    September 24, 2014

    Dear Amy: I am "old school" when it comes to this particular situation, and I am sure I will get flamed by other readers if you publish this letter.

  • Ask Amy: Unemployed couple want fancy wedding

    September 23, 2014

    Dear Amy: Our son recently got engaged. He is 26 and after spending eight years in college, he did not get a degree. He and his fiancee (an only child) live with her parents.

  • Ask Amy: Parents of cyberharassment victim seek advice

    September 22, 2014

    Dear Amy: My 25-year-old daughter briefly dated a man she met in church last December.

  • Ask Amy: Buried feelings resurface over long-ago cheating

    September 20, 2014

    Dear Amy: I married my girlfriend when we were 17. She was pregnant. We have been married for over 25 years. Our marriage has been happy and successful.

  • Ask Amy: Statute of limitations on dating a friend's ex has passed

    September 19, 2014

    Dear Amy: My best friend of 35 years dated a guy for over a year — over 10 years ago.

  • Ask Amy: How to heal after an affair? Apologize, to start

    September 19, 2014

    Dear Amy: My husband of 34 years had an affair with a co-worker, lasting for a year. He has had at least one other affair that I know of.

  • Ask Amy: Foster parents struggle with questions after loss

    September 18, 2014

    Dear Amy: My husband and I have been foster parents to a sibling group of three young children for the past year and a half.

  • Ask Amy: Breakup paves bumpy path for devastated man

    September 17, 2014

    Dear Amy: I am in my 30s. Last year my fiancee broke up with me. Afterward I did absolutely everything to make her see that was not the best decision for us. I was blindsided and feel it was my fault that I let this breakup happen.

  • Ask Amy: Husband's habit puts marriage at risk

    September 16, 2014

    Dear Amy: I have been married for almost 10 years and have caught my husband with various forms of pornography. Recently I found out he has been getting erotic massages and calling "fantasy" phone lines. I'm devastated because he has betrayed my trust and our wedding vows.

  • Ask Amy: Blended family experience is not a smoothie

    September 15, 2014

    Dear Amy: My husband has two children from a previous marriage. I have an 8-year-old daughter from my marriage (her father died). My husband and I also have a 1-year-old child together. I have worked very hard trying to create a family together.

  • Ask Amy: Toxic, bickering parents worry young adult

    September 14, 2014

    Dear Amy: My parents are in their late 60s and early 70s, and to say they "bicker like an old married couple" would be a huge understatement. It feels as though every other word that comes out of their mouths is full of hate for each other. Every little thing either does annoys the other to the point of yelling and screaming. My father is disabled, and I, 23, still live at home to help him with day-to-day stuff, taking care of the house, etc.

  • Ask Amy: Wife goes through 'change'; husband is left behind

    September 13, 2014

    Dear Amy: When we were dating, my wife was the sweetest woman in the world. She didn't make a move without asking me.

  • Ask Amy: Dorm room nudity worries boyfriend

    September 12, 2014

    Dear Amy: I attend a small college in Wisconsin. I live in a dorm. My girlfriend lives in the same dorm on a different floor.

  • Ask Amy: Dad worries about kids' media habits

    September 11, 2014

    Dear Amy: My wife and I have three great kids, ages 9 to 15. We live in an affluent community where most kids have "smart" devices and all manner of video game options at home. I am not against technology, but when my kids had free time this summer, their first choice was to either watch movies or entire television series online — or play video games. If left unattended, they can remain glued to their screens for hours.

  • Ask Amy: Granddaughter with Cinderella status should ditch the castle

    September 10, 2014

    Dear Amy: My son had a daughter when he was 19. Although he did not marry the child's mother, his daughter lived with him 50 percent of the time.

  • Ask Amy: Niece terrorizes and bullies entire family

    September 8, 2014

    Dear Amy: My 13-year-old niece, "Heather," is a beautiful girl. I love her but I don't like her. She has a bad attitude toward everyone. She lies constantly and is extremely disrespectful and obnoxious.

  • Ask Amy: Humiliation leads to unhealthy rumination

    September 8, 2014

    Dear Amy: A year ago I attended a sports event with three other men, one of whom I had never met. As we chatted, waiting for the game to start, this stranger commented on my appearance in a degrading and humiliating way.

  • Ask Amy: Is it ever OK to judge a friend?

    September 7, 2014

    Dear Amy: I have two friends of over 20 years who have decided it is OK to date married men. The women are in their 50s, unmarried and with no children.

  • Ask Amy: Mother-in-law's visit is not the Maine attraction

    September 6, 2014

    Dear Amy: My husband's parents left our hometown and moved to Florida 20 years ago when my three kids were babies. Now that my father-in-law has passed away, my mother-in-law comes to visit every summer for a month.

  • Ask Amy: Heartbroken dad ponders 'Ozzie and Harriet' divorce

    September 5, 2014

    Dear Amy: My 44-year-old daughter, who has been married for nearly 22 years to a wonderful man (my opinion), has just announced that they plan to divorce.

  • Ask Amy: Wife is rude toward husband with dementia

    September 4, 2014

    Dear Amy: My father-in-law has an early form of dementia and tends to repeat himself frequently. The stories he tells about the good old days or his trials and tribulations at work (he has a part-time job) are very familiar to the family.

  • Ask Amy: First responders respond to emergency query

    September 3, 2014

    Dear Amy: Now that many residences no longer have home phones with the number listed in a phone book and through 411, how do first responders contact a parent or loved one in case of an emergency?

  • Ask Amy: Nephew is a My Little Pony kind of kid

    September 2, 2014

    Dear Amy: I have a 5-year-old nephew who is starting kindergarten. He is a fantastic little boy who likes "boy" things like cars, but he really likes many "girl" things like Barbies, Minnie Mouse and My Little Pony. He is the most interesting 5-year-old boy I know.

  • Ask Amy: Grandmother worries about emotional child

    September 1, 2014

    Dear Amy: My grandchildren (a boy age 4 and a girl, who is 6) stay overnight with me once a week. Last night while putting them to bed, my granddaughter was chatting and the conversation led to her feelings.

  • Ask Amy: Mom doesn't take daughter's calls

    August 31, 2014

    Dear Amy: My mother and I agreed on a day and time to chat each week. I work during the week, and mom has been retired for many years and is living alone.

  • Ask Amy: Man should leave abusive marriage

    August 30, 2014

    Dear Amy: I am 75 years old and very sad. I have been married for 39 years. It has been very rocky.

  • Ask Amy: Boyfriend wants girlfriend to lose weight

    August 29, 2014

    Dear Amy: I've been dating my girlfriend for nearly two years. We live together and love each other. The problem is that we have very different ideas about fitness.

  • Ask Amy: Son camps on floor while visiting dad

    August 28, 2014

    Dear Amy: My sister is recently divorced. Her ex has moved in with the woman he had an affair with and is living with her and her three sons. I am concerned about the living arrangements her ex-husband has for my 10-year-old nephew when the boy is with him for his parental visitation.

  • Ask Amy: Woman wonders about dating disclosure

    August 27, 2014

    Dear Amy: I am a bisexual woman. I have a date coming up soon with "James," a guy I'm very interested in dating.

  • Ask Amy: Parental breakup takes a toll on adult daughter

    August 26, 2014

    Dear Amy: I'm a young woman in my 20s. I live some distance from my parents, but we have always been a close family.

  • Ask Amy: Woman worries as nephew becomes niece

    August 25, 2014

    Dear Amy: I'm a wife and mom of five sons under the age of 8.

  • Ask Amy: Dinners on the deck are a free-for-all

    August 24, 2014

    Dear Amy: We have dinners on our deck and serve the meal buffet-style. Guests are served first, and I finish up by covering the dishes with plastic wrap after I have my plate filled.

  • Ask Amy: Baby-sitting grandma puts freedom before safety

    August 23, 2014

    Dear Amy: I have a concern about how my mother-in-law baby-sits my toddler son.

  • Ask Amy: Guess who's coming to dinner? Bedbugs!

    August 22, 2014

    Dear Amy: I host a dinner once a year for a group of friends. One of the couples in our group told us they have bedbugs in their house. They are NOT doing anything about it. They moved the furniture away from the wall and seem to think that's all they need to do.

  • Ask Amy: Long-term marriage is lonely, lacks spark

    August 21, 2014

    Dear Amy: I have been married for more than 20 years to a very nice man who is a good father. We generally get along, but we don't have much of a romantic relationship.

  • Ask Amy: Funeral director can't bury job frustration

    August 20, 2014

    Dear Amy: I work as a funeral director and embalmer in a small, family-run funeral home. I take a lot of pride in my work. I spend countless hours and tons of energy ensuring that every detail of my clients' funerals goes off without a hitch.

  • Ask Amy: Dad's debts litter daughter's property

    August 19, 2014

    Dear Amy: My father has been living with my fiance and me for almost two years. The idea was that he would find his own place as soon as he could. We never asked him for anything except to tinker around and fix things around our place.

  • Ask Amy: Mom says daughter's guy isn't good enough

    August 18, 2014

    Dear Amy: My 24-year-old college-graduate daughter has been dating a young man, "Reggie," for three years. He is still finding his way, as are most millennials at that age.

  • Ask Amy: Man wants to reinvent his dating life

    August 17, 2014

    Dear Amy: I am a 32-year-old male. I have been in a string of monogamous relationships for the past 18 years, the shortest of which was one year and the longest, ending in divorce two years ago, was 81/2 years. All of my relationships (5 in total) were back to back — no courting period, zero to 60 really fast.

  • Ask Amy: Parents want others to include child

    August 16, 2014

    Dear Amy: My son is in fourth grade. He is involved in a sport each season. Due to the size of the school, he is on teams with the same group of boys over and over.

  • Ask Amy: Single mom worries about ex's family

    August 15, 2014

    Dear Amy: I have a 3-year-old child. During the pregnancy it became very clear I would be a single parent. My ex is not able to provide a stable environment for our daughter. He drinks heavily and involves himself with people (and some family members) who do illegal activities.

  • Ask Amy: Guests' dietary needs frustrate hostess

    August 14, 2014

    Dear Amy: We recently moved out of state and have an open-door policy, which means a steady flow of visitors. Many of them can barely afford the trip, so we usually pick up food and other costs.

  • Ask Amy: Maturity, not age gap, is key to relationship

    August 13, 2014

    Dear Amy: I have a great boyfriend. He's kind, sweet, smart and funny. We love to be together and to talk, just the two of us. When I'm at work and we're apart, I look forward to being with him.

  • Ask Amy: Gossip transforms teacher into terrible teen

    August 12, 2014

    Dear Amy: There is a teacher at the local high school who I see at many social, school and sport events. She is always telling stories about the students at the school to anyone who will listen. These stories are highly confidential in nature, such as a young adult who was hospitalized for depression and a suicide attempt, a child who has anorexia and an anxiety disorder, parents who are going through a nasty divorce, etc.

  • Ask Amy: What happens when good men do nothing?

    August 11, 2014

    Dear Amy: Several years ago a co-worker I was friendly with suggested we get together on a day off and barhop, shoot some pool and drink some beer. We met at a bar we both knew about and then left in his car.

  • Ask Amy: Infidelity issues dominate column

    August 10, 2014

    Dear Readers: Your questions and dilemmas never take a holiday, but occasionally I must. This year I'm spending a week pursuing a rigorous summertime schedule of mini-golf, water slides and go-kart racing. This week's "best of" columns come from deep within the Ask Amy vault. Like a soft-serve twisty cone, they are sometimes even more enjoyable as a second helping.

  • Ask Amy: During vacation, office issues dominate

    August 9, 2014

    Dear Readers: Your questions and dilemmas never take a holiday, but occasionally I must. This year I'm spending a week pursuing a rigorous summertime schedule of mini-golf, water slides and go-kart racing. This week's "best of" columns come from deep within the Ask Amy vault. Like a soft-serve twisty cone, dilemmas sometimes beg for a second helping.

  • Ask Amy: Weddings create timeless dilemmas

    August 8, 2014

    Dear Readers: Your questions never take a holiday, but occasionally I must. This week's "best of" columns come from deep within the Ask Amy vault. Like a soft-serve twisty cone, they are sometimes even more enjoyable as a second helping.

  • Ask Amy: Friendship issues challenge readers

    August 7, 2014

    Dear Readers: Your questions and dilemmas never take a holiday, but occasionally I must. This week's "best of" columns come from deep within the Ask Amy vault. Like a soft-serve twisty cone, they are sometimes even more enjoyable as a second helping.

  • Ask Amy: Awkward issues deserve artful dodges

    August 6, 2014

    Dear Readers: Your questions and dilemmas never take a holiday, but occasionally I must. This week's "best of" columns come from deep within the Ask Amy vault. Like a soft-serve twisty cone, they sometimes demand a second helping.

  • Ask Amy: No vacation from teen parenting questions

    August 5, 2014

    Dear Readers: Your questions and dilemmas never take a holiday, but occasionally I must. This year I'm spending a week pursuing a rigorous summertime schedule of mini-golf, water slides and go-kart racing. This week's "best of" columns come from deep within the Ask Amy vault. Like a soft-serve twisty cone, they are sometimes even more enjoyable as a second helping.

  • Ask Amy: Dating during a 'dim-life' crisis

    August 4, 2014

    Dear Readers: Your questions and dilemmas never take a holiday, but occasionally I must. This year I'm spending a week pursuing a rigorous summertime schedule of mini-golf, water slides and go-kart racing. This week's "best of" columns come from deep within the Ask Amy vault. Like a soft-serve twisty cone, they are sometimes even more enjoyable as a second helping.

  • Ask Amy: Intervention with an alcoholic can be tricky

    August 3, 2014

    Dear Amy: My friend of over 50 years was always a heavy drinker. Recently his drinking has become a problem. He becomes very loud and opinionated. He has ruined the last four or five times we have been out with our wives, once even getting in a fight. We are both in our 70s.

  • Ask Amy: Sleepovers becoming a relationship issue

    August 2, 2014

    Dear Amy: My partner (whom I have been living with for two years) is a loving, wonderful man. We live in the country, about an hour outside of our home city.

  • Ask Amy: Motorcycle mama won't wear helmet

    August 1, 2014

    Dear Amy: How can I convince my motorcycle-riding mom to wear a helmet?

  • Ask Amy: Grandparents favor male child over baby girl

    July 31, 2014

    Dear Amy: My new daughter is almost 4 months old, and I feel as though my in-laws don't love her as much as they do her male cousin, who is 2.

  • Ask Amy: 'Just friends' with ex? Unlikely

    July 30, 2014

    Dear Amy: My ex and I have a long history, and I guess we are (sort of) friends. We both loved each other very much but we fought way too much, which made the relationship impossible.

  • Ask Amy: Military wife doesn't want more Facebook friends

    July 29, 2014

    Dear Amy: My husband is active-duty military. We move quite often. There is a Facebook page dedicated to the military spouse community in most locations. They are great resources for newcomers with numerous questions.

  • Ask Amy: Grandma wants to charge for sitting

    July 28, 2014

    Dear Amy: My mother raised 12 children — 8 girls and 4 boys. None of us asked her to baby-sit our children, as we felt her work was done. We would visit weekly and watch her enjoy interactions with our children.

  • Ask Amy: High schooler worries about college cost

    July 27, 2014

    Dear Amy: I attend a private high school. The price tag on that leaves my parents in a tight financial spot. My parents know my tendency to worry, so they try to hide any financial troubles and sugarcoat my world. I appreciate their intentions. However, I would rather they not hide reality from me.

  • Ask Amy: Time to recover from 'worst week ever'

    July 26, 2014

    Dear Amy: I have had an especially horrible week.

  • Ask Amy: Exes awkwardly try to reunite

    July 25, 2014

    Dear Amy: My ex-girlfriend and I dated for almost three years and have now been broken up for a year.

  • Ask Amy: Senior daters disagree about intimacy

    July 23, 2014

    Dear Amy: I am a good-looking, active senior widower. I look 10 years younger than I am. I've been dating an attractive widow (10 years younger) for nearly a year.

  • Ask Amy: Depressed guest rules roost, then flies coop

    July 22, 2014

    Dear Amy: My wife's friend has been staying with us for the past four months. She took time off to work on some stressful career issues and deal with her depression.

  • Ask Amy: Daughter wants to reach out to jailed father

    July 21, 2014

    Dear Amy: Seven years ago my father was arrested for having sex with a 16-year-old girl. He was sent to prison for seven years and will be released in about a month.

  • Ask Amy: Girlfriend wants her honor defended

    July 20, 2014

    Dear Amy: Last night my boyfriend and I went to a party. We ran into someone who used to be very rude to me, to the point where he once threatened me physically. This is all because I used to be in the same social circle as his ex.

  • Ask Amy: Introvert struggles with sharing

    July 19, 2014

    Dear Amy: Due to family issues stemming from my mother's death, I have severe trust issues with people. I don't like getting close to people because everyone I grew up with has either abused me in one way or another, lied to me about major things (such as the identity of my own father), or broken me down using my mother's death as ammunition.

  • Ask Amy: Neighborhood drama creates no-win situation

    July 18, 2014

    Dear Amy: We live on a lovely little street where we frequently socialize with five other families, often in a large group.

  • Ask Amy: Inmate worries about romance with distant cousin

    July 17, 2014

    Dear Amy: I'm an inmate incarcerated for financial crimes. I have been down for three years (this time). I'm expected to be released in a few months.

  • Ask Amy: Son's STD medication scares mom

    July 16, 2014

    Dear Amy: My youngest son, "Steve," is 20 and had a few struggles in his teenage years.

  • Ask Amy: Mother excels at investigating, not parenting

    July 15, 2014

    Dear Amy: I am a college student. My mother and I have a great relationship — I feel like I can tell her anything — but there is one problem that has become increasingly frustrating. If I give her the name of a guy I would maybe consider dating, she insists on conducting extensive Internet searches until she has found his hometown, his high school activities, his parents' professions, his past girlfriends — everything.

  • Ask Amy: Manipulative mom tests notion of normalcy

    July 14, 2014

    Dear Amy: My mother is very manipulative and controlling.

  • Ask Amy: Family fundraiser doesn't sit well

    July 13, 2014

    Dear Amy: My cousin "Larry" was diagnosed with liver cancer. His mother, siblings and I arranged a fundraiser benefit and opened up a bank account in his name to raise money to cover his medical costs.

  • Ask Amy: Wife's snooping a problem

    July 11, 2014

    Dear Amy: I have never had reason to be concerned about my husband's fidelity, but a single event has got me worried, and I need your advice. Last week I sat next to him, grabbed his cellphone and punched in the password (I know the password because I have seen him enter it and it's quite simple). He looked over, saw what I was doing, and literally batted the phone out of my hand. He then proceeded to admonish me for "snooping."

  • Ask Amy: Being with a married man has a downside

    July 10, 2014

    Dear Amy: My boyfriend of four years is married. He and his wife separated months before we got together, and I am sure he has had limited to no contact with her while he is with me. But as I get older and friends are becoming engaged and married, I find myself wanting those things too.

  • Ask Amy: Bring depressed ex into friendship fold

    July 9, 2014

    Dear Amy: My ex-partner and I split up about seven months ago after living together. He is significantly older than I am. It was his decision. Although it broke my heart, I wanted him to be happy so I moved out. I moved on with my life and found a really great guy that I love very much.

  • Ask Amy: Woman questions her orientation

    July 8, 2014

    Dear Amy: My boyfriend and I have been together for five years. We were long distance for four years, and then last year I moved to Florida to be with him. He has always said he doesn't want to live anywhere other than Florida.

  • Ask Amy: Keeping accidental sneaker freebie is unethical

    July 7, 2014

    Dear Amy: Last week my wife and I purchased three pairs of sneakers at a store. The service was poor and the experience was frustrating.

  • Ask Amy: Jewish family receives Mass cards

    July 6, 2014

    Dear Amy: My sister-in-law has been sending cards for "The Holy Sacrifice of the Mass" to our Jewish family for holidays.

  • Ask Amy: Two sons engage in romantic drama

    July 5, 2014

    Dear Amy: We have two sons, "Paul," 36, and "Michael," 33. Paul finally married his long-term girlfriend "Tasha" after a long and tempestuous relationship marked by bitter breakups and tearful returns — with one arrest along the way.

  • Ask Amy: Farmer's dirty hands bother girlfriend

    July 4, 2014

    Dear Amy: I'm in a long-term relationship with a man who lives on a farm. He's wonderful, but he has some rough edges, most of which I'm OK with. The one thing I can't accept (and he seems to think it is just silly quibbling) is his dirty hands and fingernails.

  • Ask Amy: Mom violates her child's Facebook privacy

    July 3, 2014

    Dear Amy: My mother has been using Facebook more frequently in the last few months, and I think that's fine.

  • Ask Amy: Wife wants to reconcile family to cheating husband

    July 2, 2014

    Dear Amy: My family hates my husband because he cheated on me.

  • Ask Amy: Old photo stirs up new emotions

    July 1, 2014

    Dear Amy: I recently found a photo of my wife posing with an old boyfriend. She was 19 years old and very beautiful. They were walking arm in arm.

  • Ask Amy: Perfect parents seek to help sister's family

    June 30, 2014

    Dear Amy: My wife and I have two wonderful kids. Our 5-year-old daughter is polite, well-mannered, outgoing and uncommonly nice. Our 18-month-old son is shaping up in a similar vein.

  • Ask Amy: Disinvited from Thanksgiving

    June 29, 2014

    Dear Amy: My sister-in-law informed me a few weeks ago that our family of three won't be invited for Thanksgiving this year. The non-invitation is for an event that is still months away.

  • Ask Amy: Niece's biggest crime is being a teen

    June 28, 2014

    Dear Amy: My niece lost her mother (my sister) when she was 10 years old. She is now 16 and spends time at my home with my husband and me (approximately once or twice a month for an overnight).

  • Ask Amy: Cash-strapped couple worries best friend

    June 27, 2014

    Dear Amy: I am worried about my best friend and her husband. They are always short of cash and do not have any savings. Their electricity has been cut off twice. They've been through numerous cars and have been in trouble with their mortgage company for consistently late payments.

  • Ask Amy: Mom worries about gay gym teacher

    June 26, 2014

    Dear Amy: My seventh-grade daughter's female gym teacher is openly gay. None of the parents or kids has a problem with this.

  • Ask Amy: Mother thinks daughter's view on single motherhood is unrealistic

    June 25, 2014

    Dear Amy: My 37-year-old daughter is three months pregnant.

  • Ask Amy: Daughter won't grow up

    June 24, 2014

    Dear Amy: I have a daughter, 20, who basically won't do anything expected of her.

  • Ask Amy: Aunt worries about Cinderella effect

    June 23, 2014

    Dear Amy: My sister died from breast cancer two years ago at the age of 50, leaving behind three kids (ages 20, 18, 17) and her husband, "Martin." Martin started dating "Laura" (no kids) about four months after my sister's death. The kids were naturally upset that he started dating so soon.

  • Ask Amy: Scripture tattoo doesn't scan well with parents

    June 22, 2014

    Dear Amy: Our adult daughter, married with children, got a tattoo with a scripture reference and a cross on the inside of her wrist. She sent us a text with pictures explaining her reason for that tattoo and the use of that particular scripture. She was excited about it.

  • Ask Amy: Frenemies on vacation

    June 21, 2014

    Dear Amy: A group of "frenemies' recently went on a trip together. I wasn't invited and didn't have any expectation of an invitation. During their trip, someone in the group took a picture of them doing their thing with what they considered a funny caption and sent it to my email (knowing that I don't participate in Facebook and would not see it there).

  • Ask Amy: Mom disses dad in front of kids

    June 20, 2014

    Dear Amy: My wife and I have been married for more than 25 years. During that time we have had our share of marital issues, mostly related to our finances.

  • Ask Amy: Petsitting requests weigh on friendship

    June 19, 2014

    Dear Amy: A good friend of mine keeps asking me to watch her dog when she goes out of town. While it seems an innocent request, there are several things about it that bother me.

  • Ask Amy: Parents undermine eating disorder recovery

    June 18, 2014

    Dear Amy: I am a 20-year-old recovering bulimic. In trying to find a way to eat normally, I gained quite a bit of weight. I'm not obese by any means; nor am I skinny.

  • Ask Amy: Sleepover etiquette for the 'modern family'

    June 17, 2014

    Dear Amy: I have a "modern family" etiquette question for you.

  • Ask Amy: Sister needs slightly tougher love

    June 16, 2014

    Dear Amy: My sister has ongoing crises in her life (her son is an addict and her partner is abusive).

  • Ask Amy: Man wants to warn suitor away from his ex

    June 15, 2014

    Dear Amy: I dated a young lady — 26 years old — who has five children by multiple fathers.

  • Ask Amy: Silence makes husband suspicious

    June 14, 2014

    Dear Amy: A while ago I found out that my wife was texting a co-worker. She does not delete anything off her phone, but she did delete these texts to this guy (who is younger and single), making it very suspicious. This caused a major rift in our relationship, and I am slowly getting over it.

  • Ask Amy: Mother emigrates, leaving questions behind

    June 13, 2014

    Dear Amy: My mother left us a year ago and returned to our home country. She told us that she was going back (after 27 years) because she couldn't afford living expenses here. She left my father, my brother, me and her grandchildren and went home.

  • Ask Amy: Daughter's friend vetoes movie picks

    June 12, 2014

    Dear Amy: My daughter has a neighborhood friend who lives down the street. They get along well, and the girl is very nice and well-mannered. The girls frequently have "late overs" on the weekends that involve pizza and movies/games.

  • Ask Amy: Relative calls her sons stupid

    June 11, 2014

    Dear Amy: I'd appreciate your take on this and your advice about what to do. A relative of mine keeps calling my son and her son (both adolescents) "Stupid 1 and Stupid 2" for their antics together. She even introduces them this way.

  • Ask Amy: Dad worries about introducing girlfriend

    June 10, 2014

    Dear Amy: My ex-wife and I have two beautiful, well-adjusted daughters, both in graduate school.

  • Ask Amy: Family fights over deceased woman's possessions

    June 9, 2014

    Dear Amy: My husband and I were the primary caregivers for my mother-in-law. His sister moved out of state and came for visits during the summer and the holidays, but would not help with the care of her mother.

  • Ask Amy: Girlfriend keeps guy, friends separate

    June 8, 2014

    Dear Amy: I recently celebrated my one-year anniversary with my girlfriend. I love her, and we get along great. We are very compatible, and I thought integrating our teenage children would be our biggest challenge.

  • Ask Amy: Teen driver needs limits

    June 7, 2014

    Dear Amy: Our 17-year-old daughter would like to get her driver's license.

  • Ask Amy: Man has trouble coming out to mom

    June 6, 2014

    Dear Amy: I am a gay man and am having a horrible time coming out to my mother. I have an amazing boyfriend, and I love him dearly but it hurts not being able to tell her that I am gay.

  • Ask Amy: Peer pressure to marry confounds young adult

    June 5, 2014

    Dear Amy: Perhaps you can shed some light on the perplexing behavior I am witnessing among my group of friends.

  • Ask Amy: Grandparent seeks connection to baby

    June 4, 2014

    Dear Amy: Our daughter and her partner are expecting a baby this summer. My husband and I are thrilled, but I'm struggling with an issue.

  • Ask Amy: Troubled times may call for trial separation

    June 3, 2014

    Dear Amy: I am at the end of my rope. We have an 11-year-old son with ADHD who can be very challenging. When our son is being difficult my husband intimidates and antagonizes, yells obscenities and sometimes hits or kicks him unless I intervene.

  • Ask Amy: Tips to stop fighting

    June 2, 2014

    Dear Amy: My boyfriend and I seem to fight every time we are together (daily). We have boiled it down to the fact that we are both insecure and do not yet fully trust each other. On top of that, it seems that we cannot communicate and hear each other well.

  • Ask Amy: Conflict over dad's girlfriend

    June 1, 2014

    Dear Amy: Five years ago, my husband left me for his younger co-worker. He saw our two daughters (9-year-old twins) only twice a week, and never kept them overnight.

  • Ask Amy: Husband wonders about wife's past partners

    May 31, 2014

    Dear Amy: My wife and I have been together for 25 years. We have four beautiful children. We started dating just after high school. I had had only one previous sexual partner and told her everything. She told me about several people she'd been with, mostly mutual friends from high school.

  • Ask Amy: Mom dreads letting kids stay at grandpa's

    May 30, 2014

    Dear Amy: I am the mother of three children, ages 3, 7 and 9. My father (their grandfather) is very involved in their lives and he and his wife often take one of them for the day or the weekend.

  • Ask Amy: Mom copes with carping over unengaged daughter

    May 29, 2014

    Dear Amy: My daughter is nearly 30 and has been living with her boyfriend for four years. They have a sweet and respectful relationship, and we like him very much. He is very busy outside of work, and she has completed an advanced degree and landed a terrific job. She wants kids eventually, and she has told her boyfriend that.

  • Ask Amy: Young marriage is on the rocks

    May 28, 2014

    Dear Amy: I have been married to my husband for less than a year. Sadly, I feel he has misrepresented himself and this marriage is not at all what I had envisioned or signed up for.

  • Ask Amy: Phone calls upset son, fiancee

    May 27, 2014

    Dear Amy: My fiance's mother is a monster. He gets upset any time they speak. The latest incident was because he had not been in touch with her since Christmas.

  • Ask Amy: Infidelity gets in the way of anniversary

    May 26, 2014

    Dear Amy: A very friend of mine recently celebrated her two-year wedding anniversary. Unfortunately, this joyous event was marred by the discovery that her husband had cheated on her — for the third time (that we know of).

  • Ask Amy: Different dads a complication

    May 25, 2014

    Dear Amy: I have a 4-year-old daughter. Her father and I separated when she was 1, but he and his family have always been very loving and very involved in her life.

  • Ask Amy: Daughter wants no contact with mom

    May 24, 2014

    Dear Amy: When I was a freshman in high school, I decided that I no longer wanted to have any relationship with my mother. I could articulate each reason, but you don't have enough space, and I'd rather not remind myself of some of the trauma.

  • Ask Amy: Grandpa's bigotry prompts woman to stay in closet

    May 23, 2014

    Dear Amy: My daughter is dealing with depression issues and recently told me she is gay.

  • After dinner, they grapple for the check

    November 4, 2012

    Dear Amy: My girlfriend is great. Her parents are very prosperous. Whenever we go out to dinner, my girlfriend's father lunges for the check and won't let us pay. I swear I try to get it but don't want to create a scene.

  • Sudden estrangement may be sign of domestic abuse

    November 3, 2012

    Dear Amy: My husband and I are heartsick over a request from our son to refrain from having any contact with him or our daughter-in-law. They have been married for five years, and we feel we have always been kind, generous and supportive of them.

  • Grandfather holds the secret to his sadness

    November 1, 2012

    Dear Amy: More than 50 years ago I met a girl, and we started dating. A few months later she told me she was expecting a baby, but she said the child wasn't mine. We got married and had two more children and a nice life but divorced after 15 years.

  • Aunt's concern may stretch boundaries

    October 31, 2012

    Dear Amy: My brother-in-law is a textbook case of narcissistic personality disorder. He has three young-adult children. Their mom died when they were young. They have put up with years of his raging at them and putting them on pedestals.

  • Girlfriend needs to lose her boyfriend's weight

    August 4, 2012

    Dear Amy: I have been dating my girlfriend for three years, and I really love her. We get along in all aspects of our relationship. Our relationship stills feels fresh. I do think she is beautiful, too, but in the last year or so she has started to gain weight.

  • Monster-in-law insists on baby name

    July 30, 2012

    Dear Amy: I cannot deal with my monster-in-law. She's bossy, antagonistic, and gossips about my personal business far too much. As much as I try to care about her, my dislike for her has been surfacing more and more.

  • Bachelorette bridal bells ring like ka-ching

    May 12, 2010

    Dear Amy: I'm a bridesmaid for an old friend this summer, and she has chosen a three-day destination bachelorette party.

  • Parents perplexed over snarky teen

    March 1, 2010

    Dear Amy: I'm at a loss as to how to deal with my 16-year-old daughter and to teach her how to "play nice." She is stunningly beautiful but lacking in sensitivity and social skills needed to get along well with her peers. At her school, she acts rudely toward others. Her humor toward her friends reeks with sarcasm and can be very hurtful. She will only talk to a few people.

  • Paying for pizza poses problems

    February 28, 2010

    Dear Amy: My 16-year-old son and his friends get together every now and again at one another's homes to play video games or watch a movie.

  • Book club reads Sartre’s ‘No Exit’

    February 27, 2010

    Dear Amy: I have been a member of a book club for the past few years. Recently, the composition of the book club has changed. My close friends have moved away and new members have joined the group. The problem is that I work with all the people in the group and am their boss.

  • Office Santa delivers blue Christmas

    February 26, 2010

    Dear Amy: I'd like your take on a situation at work. It is customary in our firm for bosses to give their assistants holiday presents at the end of the year. These gifts can range from hundreds of dollars in cash to significant gift cards, jewelry, etc.

  • Office ogler concerns co-worker

    February 25, 2010

    Dear Amy: In an effort to build team spirit, our office had a group outing. My friend, an administrative assistant in the firm, had a meltdown, cried and panicked about the group activity we were going to do.

  • Expectant parents need their Z’s

    February 24, 2010

    Dear Amy: I am 8 1/2 months pregnant with my second child. I am a stay-at-home mom. Unfortunately, my pregnancy is causing me to snore. My husband wakes me up throughout the night to tell me to stop or get me to change positions.

  • Abused dad should take the kids and leave

    February 23, 2010

    Dear Amy: My sister has been emotionally abusing her husband for years. Recently, I learned from my brother-in-law that she has started to physically abuse him by slapping, biting and punching him. She expects my brother-in-law to meet unrealistic expectations, and when he does not meet them, she lashes out at him.

  • Granny's a nanny, so pappy protests

    February 22, 2010

    Dear Amy: My mother is a beloved member of our family.  Everyone who meets her loves her instantly. Because mom is so great and such a fun person to be around, whenever I or one of my siblings travels with our families, we will often invite mom and pay her way so she can join us.  

  • When abuse won't stop, it's time to leave

    February 21, 2010

    Dear Amy: I have been married for nearly 41 years.

  • Nursing home worker crosses the line

    February 12, 2010

    Dear Amy: My mother and " Barbie" started working in a nursing home more than 25 years ago and are good friends.

  • Father, bride tussle over wedding bill

    February 11, 2010

    Dear Amy: I have a 30-year-old daughter who just finished a short-lived marriage to a useless alcoholic. Within a few days of the ink getting dried on the papers, she announced she is engaged to a really nice guy (he is).

  • Texting friend needs to get the message

    July 24, 2009

    Dear Amy: I have a good friend who is very nice, very thoughtful and very dependable. Whenever anyone needs to reach her, my friend is just one text message away. But that is just what seems to be the problem—she is always reachable and her phone is always there, ringing off the hook with text messages.

  • 'Open' relationships don't work unless both parties are happy with the arrangement

    July 5, 2009

    Dear Amy: For the past few years, I have been in a long-distance, long-term but "open" relationship.

  • Wife excluded from party planning

    June 23, 2009

    Dear Amy: My husband and I have been married for almost two decades.

  • Irish teen's friends try to mimic dialect

    June 18, 2009

    Dear Amy: Both of my parents are Irish immigrants, so I've been raised saying things like "me coat" and calling my mother "Mum."

  • Parents out of money and patience

    June 5, 2009

    Dear Amy: Unbeknownst to us, our 23-year-old daughter ran up a large credit card debt in her last year of college, which she attended on an athletic scholarship.

  • Phone ringing off hook for teen son

    June 2, 2009

    Dear Amy: My son "James" goes to a special school for kids with disabilities. He has a learning disability but is very nice looking, competitive in sports and, most of all, a very nice young man. That is how he was raised.

  • Visiting elderly parents a tedious task

    May 29, 2009

    Dear Amy: My partner and I have a problem dealing with his elderly parents' lack of social skills.

  • Wife's friendship swayed by business deal

    May 25, 2009

    Dear Amy: My husband and his business partner, "Greg," had a friendly parting of the ways a little more than a year ago. We live in a small community, so we see Greg and his wife, "Pat," fairly often.

  • Not a mom, not 'happy' again on Mother's Day

    May 17, 2009

    Dear Amy: Another Mother's Day has come and gone and I still don't know how to deal with the "Happy Mother's Day" greeting I get when I go to a store.

  • Tight budget no reason for couple to start food fight

    May 10, 2009

    Dear Amy: My husband and I have been married for six years.

  • Fiance's shyness could be a disorder

    May 8, 2009

    Dear Amy: My fiance and I are shy people and we often just stay to ourselves. When I am around his family and friends, I leave my comfort zone and I appear warm, friendly and social even though I'm nervous. When he is around my family he is very quiet, answers questions with a "yes" or "no," and doesn't make eye contact.

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