One of the “greatest heartbreaks” Dr. Shoshana Ungerleider hears from her patients is that many wish they’d asked their parents more questions.
“By the time that we get to this realization that we wanted to know something, it’s sometimes too late to ask,” says Ungerleider, an internal medicine physician and founder of End Well, a nonprofit that aims to change the way people talk about and plan for the end of life. “It’s not just about collecting stories, although there’s beauty and power in that. It’s about connection—and honoring someone while they’re still able to feel it and experience it.”
[time-brightcove not-tgx=”true”]Where do you even start, especially if your conversations tend to center on the mundane aspects of life? We asked experts to share the most meaningful questions to ask your parents while you still can.
“What’s something you’re into right now that I might not know about?”
If you’re not used to having serious conversations with your folks, ease in with some low-key warm-ups. “Any kind of novel or low-stakes prompt” will do the trick, says Jenny Shields, a psychologist and bioethicist in Houston—like asking mom or dad about fun new interests. “People love to share about themselves, and it kicks them out of autopilot,” she adds. “It’s light, it gets the juices flowing, and it helps us get more comfortable asking those harder questions.”
“If your life had chapters, what title would you give this one?”
This is another way to encourage people to open up—especially if they typically avoid getting vulnerable. “It might not be easy to say, ‘I’m literally in hell right now, and everything’s awful,’” Shields says. Sharing a quick, creative one-liner about how life is going, on the other hand, is more doable. Think of your parent’s response as a “thermometer of where they’re at,” she urges. “It gives you a little signal of what’s to come, and allows them to slowly start to self-disclose in a more safe way.”
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“When do you feel most calm and grounded these days?”
When you’re ready to dig a little deeper, ask your parents when they feel the most at peace. The answer will be revealing, Shields says—what if they say “never”? You might bond over feeling like life is too chaotic; or, you could share the ways you squeeze in time to recharge: “I take five minutes in the morning to have my coffee on the porch.” The conversation can also work two ways to build empathy. “You might say, ‘I feel like I have no time—the kids are so young, there’s not a moment to breathe,’” she says. “Then they can say, ‘Gosh, I remember what that was like. You’re right—it’s so hard.’”
“What do you wish the most for my life?”
It can be meaningful to ask your parents to share their most deeply held hopes for their children (that’s you) and, if relevant, their grandchildren. While they surely want you to be successful and achieve your goals, “other things—interpersonally and relationally—are so incredibly important, too,” Ungerleider says. That might include “talking about how we live our lives and love each other and care for each other.”
“What were your most painful moments?”
It needs to be the right time to bring up such a sensitive subject—but the way your parents respond can give you insight into their most formative experiences. That’s especially true if you pair it with a follow-up question: “What brought you out of the lowest point in your life?” “You could really learn from seeing how somebody faced an obstacle or adversity, and then how they came out of it,” Ungerleider says. Your mom or dad might be more resilient than you realized—which could inspire you for years down the road.
“What’s something you’ve changed your mind about in the past few years?”
This is one of Shields’ favorite prompts—she asks it of all the students in her psychology class. It encourages them to slow down and consider the fact that they have flexibility around the way they think, she says; nothing is static.
Read More: 9 Ways to Set Healthy Boundaries With Your Parents
Plus, your mom or dad might surprise you. Maybe they’ve changed their mind about something the two of you previously disagreed on. “It helps start that process of reframing old hurts and old patterns,” she says. “We all learn new things as we grow. It’s normal, and we want to build that empathy for one another.”
“What do you wish more people knew about you?”
The way your parent responds will help you understand what qualities they value most about themselves. Maybe you’ll learn that your mom really likes to be recognized for how silently she serves everybody around her when she’s hosting, for example. “Then you, as a child, can recognize the next time she does something like that—you’ll have the ability to affirm her,” Shields says. “We all want to feel seen, and what matters to one person might not be the thing that the other thinks of them. It opens up the door to, ‘Who am I? And what do I care about?’”
“What did love look like in your family growing up?”
Learning what kind of family dynamic your parents grew up in can shine surprising light on your own upbringing. Shields suggests following-up with questions like: “Were there emotions that weren’t welcome in your house? What happened if you got upset or needed comfort? Were there any unspoken rules?” You might discover your mom wasn’t allowed to talk back, and dad would get in trouble if he cried—which then opens the door to talking about how those rules shaped who they had to be and who they became. All of a sudden, experiences from your own childhood, which you might still harbor grudges about, could make more sense.
“What were you afraid of when you became a parent?”
There are lots of different layers that affect someone’s journey into parenthood: “We’re talking about cultural influence, historical influence, generational influence, and what might have been happening in their family lineage,” says Miranda Malone, a grief coach, therapist, and founder of the Mother Loss Collective. She lost her mom when she was just 5 months old, which triggered a lot of fear around having her own child: “Am I going to be there for him? Am I going to die early and leave him?”
Read More: 14 Things to Say Besides ‘I Love You’
Asking your mom or dad what they were afraid of as they stepped into their new roles helps humanize them, Malone says, while proving that they didn’t have it all together either. “It reminds us our parents had their own fears, doubts, and stories that shaped how they showed up for us,” she says. “Our parents are just people who had children.”
“What do you hope people say about you after you’re gone?”
Malone’s mom passed away at age 19—and everything she knows about her comes from other people. That instilled a strong belief in the importance of talking about legacy. Asking your parents how they hope to be remembered “shines a light on how they see themselves, how they view what type of parent they were, what type of friend they were, and what type of partner they were,” she says.
Not enough people think about and talk about this kind of thing, Ungerleider adds—which is understandable. It might feel like inviting sadness and grief into your relationship before you need to, but that’s preferable to being consumed with regret down the road. “There’s some beautiful legacy work you can do leading up to whenever that eventual end is,” she says. “Certainly thinking about what you’re physically leaving behind, or the things you’ve created in your life, but also how you hope people felt in your presence, and the experiences they had with you.”
Wondering what to say in a tricky social situation? Email timetotalk@time.com
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