Add Yahoo as a preferred source to see more of our stories on Google. Dear Annie: My best friend, “Claire,” has been dating her boyfriend, “Jay,” for three years. I really liked him when they first ...

My friend has been bewildered by her difficulty in finding a steady relationship, so I pressed him as to why. He told me they went to a swanky bar, and she—wait for it—ordered a plain glass of milk.

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 Abby advises someone who is trying to help their friend navigate a struggling marriage with a cheap husband during the holidays. Prostock-studio DEAR ABBY: My friend is married to a penny-pincher ...

Dear Annie: I have a friend, “Marcy,” whom I’ve known for about six years through a mutual group of acquaintances. She was very kind when my mother was alive, often coming over to help, and she has ...

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 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 ...

Dear Abby: How do I tell my friend I feel she needs a mental health evaluation? She has been my closest friend for 20 years, and we have been through many trials together. She has been married for a ...

Dear Eric: Several months ago, a friend’s boyfriend broke up with her. She is devastated over this as she loves him very much. Even though he treated her very poorly by saying she is stupid and is an ...

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 ...

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 ...