#1182, #1183, #1184: “Do I have to be friends with my sibling?” or, Advice For Relationships You Don’t Want to Lose But Don’t Want To Work At.

Hi Captain, For over a decade, I had a really bad relationship with my sister. She struggled with addiction and suicide ideation and, often, was just plain mean. I enabled her by making sure I was always available to her during her emotional crises and never saying no to anything she wanted. I got a … Continue reading #1182, #1183, #1184: “Do I have to be friends with my sibling?” or, Advice For Relationships You Don’t Want to Lose But Don’t Want To Work At.

#673: My insufferable brother is ruining all the time I spend with my family + Winter Pledge Drive.

Dear Captain, I have only one sibling, an older brother. He is in his late thirties and still lives with my parents. He's never lived on his own, whereas I moved out as soon as I could at 18. He has a BA in Accounting, he works full time, he pays rent to my parents … Continue reading #673: My insufferable brother is ruining all the time I spend with my family + Winter Pledge Drive.

Reader question #114: How do I reconnect with my estranged brother and help him form a relationship with his niece?

Dear Captain Awkward -  I write for a reality check from you and your wise readers regarding the plan I have devised going forward with my brother. The backstory: my brother's wife has chronic health problems, and some mental health issues as well (who wouldn't?). She is totally isolated from her family, and basically only … Continue reading Reader question #114: How do I reconnect with my estranged brother and help him form a relationship with his niece?