Dear Annie: My best friend, “Claire,” has been dating her boyfriend, “Jay,” for three years. I really liked him when they first started dating, but lately, she’s been confiding in me about some things ...

Dear Annie: My best friend and I have been close for over 20 years. We’ve seen each other through marriages, divorces, parenting challenges, health scares — you name it. She is the person I call when ...

Dear Eric: I grew up in a degree of poverty. Most of my friends have done “OK” financially. All of us but one is now retired and she is hoping to retire soon at age 73. She’s continued to work as ...

A reader’s patience is wearing thin with an otherwise fun and generous friend who leaves much to be desired as a conversational partner.

Dear Readers: To mark my final week writing this column, I’ve fired up the “Ask Amy” Wayback machine and am re-running some memorable Q&As culled from the last 21 years of “Ask Amy.” Dear Amy: I’m a ...

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This is part of Advice Week: Friendship Edition. We’ll help you make friends, leave them—and even sleep with them. We’ve gotten some great questions over the years about the interesting dilemmas our ...