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March 26, 2021 Mar. 26, 2021

Classic Annie's Mailbox

Dear Annie: I am in my early 50s, a widow, with five great kids, all now grown, out of college and t... Read More

March 5, 2021 Mar. 05, 2021

Classic Annie's Mailbox

Dear Annie: My husband passed away last month. His six children (who are my age) were never fans of ... Read More

March 4, 2021 Mar. 04, 2021

Classic Annie's Mailbox

Dear Annie: Yesterday, I tried to help my son do his third-grade homework. One question was: "If Sue... Read More

The Need for Personal Responsibility Jan. 20, 2021

Dear Annie®

Dear Annie: This letter is a message to "Fed Up," the reader whose husband dotes on their daughters.... Read More

Late Husband's Family Bothering Me Jan. 09, 2021

Dear Annie®

Dear Annie: I'm a 39-year-old mom of four. My husband recently passed away, in April of this year. ... Read More

November 12, 2020 Nov. 12, 2020

Classic Annie's Mailbox

Dear Annie: I am a 12-year-old boy with a problem. My dad died when I was a baby, so it's just my mo... Read More

October 22, 2020 Oct. 22, 2020

Classic Annie's Mailbox

Dear Annie: My wife and I are in our mid-70s and have no children. However, we have had pets, mostly... Read More

New Love Doesn't Replace Old Oct. 14, 2020

Dear Annie®

Dear Annie: I was troubled by one particular sentence in the letter from "Missing Love," who wanted ... Read More

Sympathy for Stepmom Oct. 11, 2020

Dear Annie®

Dear Annie: I come from a large family. Our mother died at a young age (39), and there were seven ch... Read More

September 11, 2020 Sep. 11, 2020

Classic Annie's Mailbox

Dear Annie: I am a widow in my 80s. I recently was introduced to a widower who seemed friendly and h... Read More

Demanding to Be No. 1 Aug. 31, 2020

Dear Annie®

Dear Annie: I had been living with a widowed man for over a year. After COVID-19 hit, his grown son ... Read More

Letting Off Steam Jul. 29, 2020

Single File®

Whenever someone learns what I do for a living, out pours a torrent of past dating slights. For the ... Read More

June 12, 2020 Jun. 12, 2020

Classic Annie's Mailbox

Dear Annie: Two years ago, I married "Will." We were both widowed. I had a good job, a nice home and... Read More

June 1, 2020 Jun. 01, 2020

Classic Annie's Mailbox

Dear Annie: My father-in-law died four years ago. He had struggled with some health issues for a whi... Read More

May 12, 2020 May. 12, 2020

Classic Annie's Mailbox

Dear Annie: I'm a little confused about a recent development in my life. I'm a 69-year-old male. My ... Read More

April 13, 2020 Apr. 13, 2020

Classic Annie's Mailbox

Dear Annie: I am a disabled single mother of two, and I work part time. We live in a modest mobile h... Read More

New Beau, New Woes Apr. 04, 2020

Dear Annie®

Dear Annie: I am 75. I've been single for more than 20 years. I was resigned to live my life as a si... Read More

And Now You Know the Rest of the Story Jan. 17, 2020

Tales From the Front

We recently met Jason and Andrea. They were the lawyers whose relationship turned from professional ... Read More

January 8, 2020 Jan. 08, 2020

Classic Annie's Mailbox

Dear Annie: Twelve years ago, I married my best friend, lover and the woman I believed to be my part... Read More

Three's a Crowd Dec. 27, 2019

Tales From the Front

A few months after his wife died, Jason got a call from Andrea. They're both lawyers — she spe... Read More