June 14, 2025

Dear Annie: Is my estranged brother’s new baby a good enough reason to try to mend fences?

Dear Annie: About five years ago, my younger brother “Henry” and I had a falling out over a family inheritance issue after our father passed away. Words were said that we both probably regret, but neither of us has made a move to reconnect since.

We live in the same city but haven’t spoken, even at holidays. Our mother has tried a few times to gently encourage us to make amends, but we’ve both avoided the conversation.

Now, my brother’s wife just had their first child. I found out through a mutual cousin who saw the baby announcement on social media. Part of me wants to send a card or a small gift to acknowledge the birth and maybe open the door a little. But I also don’t want it to come across as shallow or too little, too late.

Is it appropriate to reach out after years of silence just because there’s a new baby in the picture? Or should I wait for a more direct opportunity to talk through what happened before trying to rebuild any kind of connection? — On the Sidelines

Dear On the Sidelines: Births and deaths have a way of making us realize just how short life is. If a small part of you wants to reconnect with Henry, then he probably feels the same — especially with a new child in the picture.

Reach out with a card or a small gift. Down the line, you can discuss what happened five years ago. But now is a time to celebrate.


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