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Thursday, October 29th 2026

eNewspaper

Asking Eric

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Asking Eric

R. Eric Thomas, a playwright, screenwriter, best-selling author and a former columnist for Elle.com and Slate.com, will be writing a new syndicated column for the Chicago Tribune called "Asking Eric," which will replace Amy Dickinson's "Ask Amy" column. (Kap2ure Photography)

Asking Eric: Sibling’s messy home raises alarms for family

By R. Eric Thomas

October 29, 2026 at 12:01 a.m.

Dear Eric: I’m the oldest of three. My middle sibling has routinely been to the...

R. Eric Thomas, a playwright, screenwriter, best-selling author and a former columnist for Elle.com and Slate.com, will be writing a new syndicated column for the Chicago Tribune called "Asking Eric," which will replace Amy Dickinson's "Ask Amy" column. (Kap2ure Photography)

Asking Eric: Sister ponders sharing family secrets

By R. Eric Thomas

October 28, 2026 at 12:01 a.m.

Dear Eric: I have two brothers with storied pasts from 60 years ago. My older...

R. Eric Thomas, a playwright, screenwriter, best-selling author and a former columnist for Elle.com and Slate.com, will be writing a new syndicated column for the Chicago Tribune called "Asking Eric," which will replace Amy Dickinson's "Ask Amy" column. (Kap2ure Photography)

Asking Eric: Friend’s bossy behavior to boyfriend causes concerns

By R. Eric Thomas

October 27, 2026 at 12:01 a.m.

Dear Eric: I have been friends with a woman for about 12 years. We have...

R. Eric Thomas, a playwright, screenwriter, best-selling author and a former columnist for Elle.com and Slate.com, will be writing a new syndicated column for the Chicago Tribune called "Asking Eric," which will replace Amy Dickinson's "Ask Amy" column. (Kap2ure Photography)

Asking Eric: Boyfriend and college friend have conflicted history

By R. Eric Thomas

October 19, 2026 at 12:01 a.m.

Dear Eric: I’ve been dating my boyfriend for about five years. I recently reconnected with...

R. Eric Thomas, a playwright, screenwriter, best-selling author and a former columnist for Elle.com and Slate.com, will be writing a new syndicated column for the Chicago Tribune called "Asking Eric," which will replace Amy Dickinson's "Ask Amy" column. (Kap2ure Photography)

Asking Eric: Daughter’s drawing hurts mother’s feelings

By R. Eric Thomas

October 18, 2026 at 12:01 a.m.

Dear Eric: I have a typical 15-year-old teenage girl. She is my world and I...

R. Eric Thomas, a playwright, screenwriter, best-selling author and a former columnist for Elle.com and Slate.com, will be writing a new syndicated column for the Chicago Tribune called "Asking Eric," which will replace Amy Dickinson's "Ask Amy" column. (Kap2ure Photography)

Asking Eric: Sister’s ongoing conflict with father cause family stress

By R. Eric Thomas

October 17, 2026 at 12:01 a.m.

Dear Eric: I'm writing about my 64-year-old sister I'll call "Beth." We are three sisters....

R. Eric Thomas, a playwright, screenwriter, best-selling author and a former columnist for Elle.com and Slate.com, will be writing a new syndicated column for the Chicago Tribune called "Asking Eric," which will replace Amy Dickinson's "Ask Amy" column. (Kap2ure Photography)

Asking Eric: Coworker in toxic workplace wonders ‘am I the drama?’

By R. Eric Thomas

October 16, 2026 at 12:01 a.m.

Dear Eric: I really cannot tell if I’m the problem at work. I’ve been on...

R. Eric Thomas, a playwright, screenwriter, best-selling author and a former columnist for Elle.com and Slate.com, will be writing a new syndicated column for the Chicago Tribune called "Asking Eric," which will replace Amy Dickinson's "Ask Amy" column. (Kap2ure Photography)

Asking Eric: After inheriting money, friend worries about making friends uncomfortable

By R. Eric Thomas

October 15, 2026 at 12:01 a.m.

Dear Eric: My husband and I are the fortunate recipients of our parents' inheritances. We...

R. Eric Thomas, a playwright, screenwriter, best-selling author and a former columnist for Elle.com and Slate.com, will be writing a new syndicated column for the Chicago Tribune called "Asking Eric," which will replace Amy Dickinson's "Ask Amy" column. (Kap2ure Photography)

Asking Eric: Teacher traumatized by students’ crises

By R. Eric Thomas

October 14, 2026 at 12:01 a.m.

Dear Eric: I have been a teacher for 19 years. I have seen a lot....

R. Eric Thomas, a playwright, screenwriter, best-selling author and a former columnist for Elle.com and Slate.com, will be writing a new syndicated column for the Chicago Tribune called "Asking Eric," which will replace Amy Dickinson's "Ask Amy" column. (Kap2ure Photography)

Asking Eric: New work friendship sends mixed messages

By R. Eric Thomas

October 13, 2026 at 12:01 a.m.

Dear Eric: I am a male, a new female coworker started around Halloween 2025, and...

R. Eric Thomas, a playwright, screenwriter, best-selling author and a former columnist for Elle.com and Slate.com, will be writing a new syndicated column for the Chicago Tribune called "Asking Eric," which will replace Amy Dickinson's "Ask Amy" column. (Kap2ure Photography)

Asking Eric: Annual trip was friends-only until two started dating

By R. Eric Thomas

October 12, 2026 at 12:01 a.m.

Dear Eric: A bunch of friends and I usually go on vacation for Labor Day....

R. Eric Thomas, a playwright, screenwriter, best-selling author and a former columnist for Elle.com and Slate.com, will be writing a new syndicated column for the Chicago Tribune called "Asking Eric," which will replace Amy Dickinson's "Ask Amy" column. (Kap2ure Photography)

Asking Eric: In-laws get into altercation on vacation

By R. Eric Thomas

October 11, 2026 at 12:01 a.m.

Dear Eric: This past July we rented a house for our two daughters, their partners...

R. Eric Thomas, a playwright, screenwriter, best-selling author and a former columnist for Elle.com and Slate.com, will be writing a new syndicated column for the Chicago Tribune called "Asking Eric," which will replace Amy Dickinson's "Ask Amy" column. (Kap2ure Photography)

Asking Eric: Spurned stepbrother considers revenge with scandalous photos

By R. Eric Thomas

October 10, 2026 at 12:01 a.m.

Dear Words: Throw the photos away. Sending them is not going to make you feel...

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