10 family conversation starters

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What does the word family mean to you?

Growing up, I never thought much of family.

I was simply too self-absorbed to realize the importance of family relationships.

As I got older however, I started to appreciate how family shapes a lot of how we think and communicate with others. And really, family is all we have. Just ask yourself this question:

Who can you call at 3 am and will come to your aid?

Chances are, it’s someone in your immediate/extended family.

That’s why I took the effort to reconnect with my family after years of neglecting them. Thankfully, I’ve been able to do so.

We all have a role in shaping our family culture.

And it starts with one conversation at a time.

Now, rather than throwing you a bunch of conversation starters, let’s take a step back and look at the bigger picture first…

Realize how little time you have left with family

“By the time you move out of your parents’ home, you’ve already spent 93% of the time that you will ever spend with them (if they live far away). Conversely, as a parent, you will only see your kids a handful of times per year once they move out.

— Michael Simmons

This raises the stakes — each conversation might very well be the last. Make it count. But how do you start having better conversations?

Notice your assumptions

Having the intent to have better conversations isn’t enough. We are often so affected by our biases in our view of family.

Because we spend so much time with family, it’s hard to see them objectively. Kate Murphy, the author of You’re Not Listening, said:

“We actually all tend to make assumptions when it comes to those we love. It’s called the closeness-communication bias. As wonderful as intimacy and familiarity are, they make us complacent, leading us to overestimate our ability to read those closest to us.”

I don’t think it’s possible to eliminate the closeness-communication bias, but at the very least we can acknowledge that we know our family way less than we think.

Here are some questions to start getting to know your family better:

10 best conversation starters for family (in any situation)

You don’t need a hundred questions, you need a few simple, high-quality questions to connect with your family. That’s it. The rest of it is just good old conversation building (listening, paraphrasing, etc.)

Here are my go-to questions:

How are you?

The typical response is “fine” or “okay”, which isn’t helpful for a deeper conversation.

Get them to go beyond the surface by gently pushing them to share more. You could ask something like:

How are you, really?
How are you feeling?
What’s on your mind? // Anything on your mind?

How do you feel?

Emotion check-ins are highly underrated, especially when your family member is going through a tough time.

Now, not everyone is comfortable sharing their emotions. So how can you get them to open up? Start the conversation by gently guessing. Here’s how:

I might be wrong, but I noticed that you’re [emotion]…
I might be overthinking, but you seem [emotion]…
I might be reading too much into things, but I sense that you might be [emotion]…

As you hear them out, keep paraphrasing to understand what they really feel.

What are you excited about today/this week/recently?

Many family conversations revolve around errands…the day-to-day stuff. There’s nothing wrong with that, but it’s important to zoom out and learn what your family member is up to these days.

The best times of day to have deeper conversations are often during dinnertime or before bed, since you’re most likely winding down with your family.

How would you like to spend time together this weekend/holiday?

Similar to what I said in #2, it’s way too easy to do family time on autopilot (which is understandable btw, since family routines run like clockwork). To truly connect, you need to set aside time and plan activities intentionally.

Planning doesn’t have to be complicated — it’s the intent that counts. It can be as simple as going to a neighborhood cafe and chatting over coffee.

Other ways to ask include:

What would you like to do this weekend/holiday?
What do you think about visiting/trying…
How does [family activity] sound?

Have you heard about [news]… what do you think?

The day-in-day in our family can be mundane. Thankfully, the 24/7 news or internet provides us with a non-stop flood of conversation topics.

Of course, not all information is made equal. I’d focus on news that’s either on important topics that you and/or your family are interested in. That way, you can trade opinions and ideas and learn from each other in conversations.

Here are a few ways to start a conversation on current events:

Have you heard about [news]… what do you think?
What’s your take on [news]?
I heard that… and I think… What about you?
Most people think [opinion] about [news]. Do you agree/disagree?

(If you disagree — which you probably will — here’s how to do it respectfully.)

Can I get your advice/feedback on…

Your family is your best source of support in many cases, especially if they are older or more experienced. It might feel awkward to ask for help if it’s not in your family culture, but trust me: they will be flattered that you approach them!

Here are other questions that you could ask them. To help them connect with you emotionally, be vulnerable. For example:

I’m struggling with [challenge]…
I’m not sure what I should do…
I’m feeling lost…

Can I help…

Family is all about supporting each other. Now, the key is offering help that the family member actually wants, vs. being intrusive. What does this mean for you? Rather than assuming that your family member wants help in a certain way, or a certain kind of support, ask first. Here’s how:

Can I help?
Do you need help? (as disappointing as it can feel, they might not be ready for a helping hand)
How can I help?
What support do you need the most?
What’s the best way to support you on…

How to be a great leader: 31 leadership conversation questions

I’m so proud of you for…

While it’s important to support your family through tough times, research shows that it’s not as important as celebrating them in good times.

Wait, WTF? Yeah, when I first learned about this, I was skeptical. But the more I think about it… the more it makes sense. Acknowledging the other person’s happiness helps you build a bank of positive feelings about each other, which comes in handy when there’s conflict or stress.

When your family member accomplishes or experiences something positive, you can simply say “I’m so proud of you”. (Here are other phrases you can use.)

If possible, get specific by pointing out how their effort helped them achieve success.

Thank you for…

Gratitude is the rock of a meaningful long-term relationship, according to research. A less fancy way of saying this is? We all want to feel seen and heard.

Expressing gratitude can transform your entire conversation, especially when that’s the first thing you say. Here’s how to tell your family member that you appreciate them:

Thank you for…
I really appreciate that you did/said…
It means a lot to me when you…

Make sure that you don’t do a Shit Sandwich — that is, mixing your appreciation with criticism — it will confuse the other person and even make them feel resentful towards you. Start with your message of gratitude and stick with it throughout the conversation.

I’m sorry.

Conflict can lead to a deeper connection… or it can lead to a permanent crack in the relationship. To repair the relationship upfront, acknowledge your responsibility in any conflict by saying:

I’m sorry. (This is simple, but sometimes that’s all it takes!)
I’m sorry about [my words/action]…
I acknowledge what I [said/did] hurt you…
I see how [my words/action] caused you to feel…

Conversation starters on special occasions

As best as we communicate with our family day by day, commitments can get in the way of connection. And that’s why special occasions —be it holidays, birthdays, or weddings — are wonderful opportunities to have deeper conversations.

To start meaningful conversations, check out the following articles:

Conversation starters for parents, children, siblings

Depending on what role you play in the family, these conversation starters could help: