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Caught Between Sisters Oct. 08, 2025

Dear Annie®

Dear Annie: I am caught in a very difficult family situation. I have twin sisters-in-law, Tricia and... Read More

Boundaries Are Not Selfish Sep. 21, 2025

Dear Annie®

Dear Annie: I am a 57-year-old woman who has had many problems with my sister over the years. When m... Read More

When Relationships Shift Sep. 18, 2025

Dear Annie®

Dear Annie: My sister "Claire" and I have always been close, but things have shifted since she had h... Read More

Worried From Afar Jul. 02, 2025

Dear Annie®

Dear Annie: My sister and I were inseparable growing up. We talked every day, shared everything and ... Read More

Distance and Red Flags Jun. 24, 2025

Dear Annie®

Dear Annie: My younger sister and I used to be incredibly close. We talked every day, shared everyth... Read More

Sisterhood on Shaky Ground May. 31, 2025

Dear Annie®

Dear Annie: I've been struggling with my relationship with my older sister for some time now. Unfort... Read More

Seeking Peace With Sisters May. 14, 2025

Dear Annie®

Dear Annie: After living in separate cities for most of our adult lives, my older sister moved just ... Read More

Rebuilding Bridge With Brother Mar. 11, 2025

Dear Annie®

Dear Annie: Three years ago, my older brother received a $60,000 settlement, and I believe it change... Read More

Family Ties and Tough Love Jul. 15, 2024

Dear Annie®

Dear Annie: My sister is eight years younger than I am. She was homeless, so my older sister took he... Read More

Supporting Sibling's Struggles, Protecting Parents' Well-Being Jun. 28, 2024

Dear Annie®

Dear Annie: My brother, "David," has been struggling with alcohol for years, and it's starting to ta... Read More

Sisterly Snag: A Party Predicament May. 17, 2024

Dear Annie®

Dear Annie: My sister "Emily" and I were planning a joint celebration for our parents' 40th wedding ... Read More

Brother Is Out Of My Life For Good Mar. 24, 2024

Dear Annie®

Dear Annie: My only brother is 70, two years younger than me. We've not been close or communicating ... Read More

Sisterly Strife Feb. 07, 2024

Dear Annie®

Dear Annie: My problem is twofold. My nine-year relationship with "Louis" is usually a joy. We are b... Read More

Finding Love Later in Life Jan. 17, 2024

Dear Annie®

Dear Annie: How do I deal with passive-aggressive siblings? When we are together, it can be all laug... Read More

Snarky Siblings and Micromanagers Sep. 14, 2023

Dear Annie®

Dear Annie: I have a complicated relationship with my siblings. I'm the youngest of four. Now, in my... Read More

Dealing With Difficult Siblings Feb. 08, 2023

Dear Annie®

Dear Readers: The letter "Calling It Quits" about coping with an unreasonable sibling — who th... Read More

Setting Boundaries for the Sake of Family Nov. 26, 2022

Dear Annie®

Dear Annie: My mom's husband molested my sister more than 25 years ago. I was a teenager at the time... Read More

Snoopy Sister Is Monitoring My Finances Oct. 16, 2022

Dear Annie®

Dear Annie: I have never sent in anything to a column before, but I'd like to say something from a g... Read More

October 12, 2022 Oct. 12, 2022

Classic Annie's Mailbox

Dear Annie: I am 29 and have been a teacher in a small town for seven years. During this time, I hav... Read More

Mom's Dementia Is Taking a Toll on Relationship With Brother Sep. 05, 2022

Dear Annie®

Dear Annie: My brother and I are in our early 50s, and our mom has dementia. Our personal lives coul... Read More