A lot has changed since you bickered in the back seat. Update your relationship with these conversation starters.

By Sarah Robbins
Updated January 09, 2018
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Illustration: woman opening the door to 3 adult siblings
Credit: Jasu Hu

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Illustration: woman opening the door to 3 adult siblings
Credit: Jasu Hu

1 What can I do to help us grow closer?

“The beauty of having siblings is that they teach us to deal with conflict. We’ve been vying for our parents’ attention since we were born! There can be tensions or disappointments that create distance, and sometimes someone must take the first step in renewing and enriching an old bond. ‘What can I do to help us grow closer?’ is a profound question, but it doesn’t have to carry the weight of an international summit. There are so many possible answers, from ‘I think we’re close enough’ to ‘You might help more with Mom’ to ‘You should apologize for hitting me when I was a kid.’ If you feel resistance, then just shut up for a while and try again later. It’s still an expression of love—an opening of a door.”

—Jane Isay is the author of Unconditional Love: A Guide to Navigating the Joys and Challenges of Being a Grandparent Today. She lives in New York City.

2 What’s the long-term plan for Mom and Dad?

“We all go through transitions in life, and at a certain point, it becomes natural to discuss how you and your siblings might support your parents as they age. The ability to help pay for that support may differ; one of you might work for a nonprofit, for example, while another is an executive. When the conversation is triggered by an event—say, Mom falls and breaks her hip—it can quickly become emotional. It’s far better to be proactive and have a discussion when everyone is still healthy. You should ask, ‘What do we know about Mom and Dad’s financial circumstances, and what responsibilities might we have to bear, as a group, to support them as they age?’”

—Jim Sandager, a certified financial planner, is senior vice president at the Wealth Enhancement Group. He lives in West Des Moines, Iowa.

3 What do our family heirlooms mean to you?

“My brother and I are both in the antiques business, but when it comes to our own family’s estate, we think about it the way most people do: We prefer not to think about it! Dealing with heirlooms can be a charged situation. If your parents are downsizing or you’re dividing an estate, have everything appraised before anyone walks away with anything. Everyone is different: One sibling’s connection to a teddy bear might be worth far more to her than a $1,000 candelabra—but what if that candelabra is worth $5,000? Or $50,000? Having the facts about how much something is worth can help lower the risk of bad blood later.”

—Nicholas D. Lowry is president of Swann Auction Galleries in New York City and a regular appraiser on PBS’s Antiques Roadshow.

4 How can I best include your partner in family meals?

“As brothers and sisters grow up, their significant others become an important part of the sibling relationship. If you take the time to learn about them, they can help strengthen your bond. For me, that has meant asking my brother Eli what his wife Stephanie’s favorite meal is and making sure I try to bring it to the table whenever we’re together. Stephanie is Filipina, and her mother is an incredible cook. Chicken adobo, a classic dish from the Philippines, often figures into our family meals now; when my brother and I were working on the Project Foodie app, a video of that recipe became a big part of it.”

—Daniel Holzman is chef and co-owner of The Meatball Shop. He lives in New York City.

5 What do you wish I knew about you now?

“Intense yet not frequently discussed, sibling relationships can be ignored for long stretches of time, but eventually we need to deal with each other again. Our impressions of one another can get frozen in time: What we know about our siblings—or what they know about us—could now be woefully outdated or just plain wrong. Wouldn’t it be wonderful to give your sibling the opening to say, ‘Here’s what I’d like you to understand about me’ ? Don’t interrupt. It’s very loving to just sit back and absorb the answer.”

—Kelly Corrigan is the author of Tell Me More: Stories About The 12 Hardest Things I’m Learning To Say. She lives outside Oakland, California.