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How to Help Your Loved Ones During the Holidays: Start a Conversation

When the holidays are tough for someone you care about, it can be tempting not to talk about it—to plaster on a smile, keep the energy high, and avoid saying anything too heavy. But that’s often the opposite of what your friend needs. According to Sheila Heen, co-author of Difficult Conversations, starting a real conversation about what your friend is going through may be the most important gift you can give them.

Maybe you don’t know what to say. Maybe you’re worried about making your friend feel worse. In fact, saying something tells them that you’re thinking about them and you care. Tiptoeing around the elephant in the room won’t make it leave. Acknowledging that elephant is the first step toward kicking it out.

Here’s some advice for getting started:

Read the tips

Don’t wait for the perfect moment

It’s tempting to put off saying something indefinitely while you wait for the perfect moment or the perfect words. Don’t wait too long to let your friend know that you’re thinking about them. The timing and the words don’t matter as much as just saying something. You don’t need to be prepared with answers, and it’s okay to be nervous. Accept that this may be uncomfortable, and dive in anyway.


Start the conversation, even if it’s awkward

Don’t stress about finding a super-smooth way to introduce the topic. Just keep it simple. Give them a hug or a warm “Hey.” Ask how they’re doing today. Find a quiet moment and say, “You know, I've been thinking of you and wondering how you and the kids are doing” or “... how you’re holding up without your dad this Hanukkah” or “... how you’re dealing with Roberto being in the hospital.” If you’re going to see them in a public setting and don't want to put them on the spot, leave them a note ahead of time or text them to let them know you're thinking of them. If all else fails, say, “I wish I knew the right thing to say” or “I wish there were something I could say that would make things better.” That acknowledgment speaks volumes.

No matter how you start, you’re giving your friend the green light to share their true feelings. Your presence is the real message of support they’ll remember.


Don’t expect to fix things

It can be hard to walk alongside someone you care about who is in pain and not try to “fix” everything that’s wrong. Your friend doesn’t expect you to have magic words or powers to make their pain go away. The best thing you can do is to say something that lets them know that their suffering isn’t invisible to you and that you’re there for them. Try “I wish so badly I could take away your pain. I promise I’ll be here for you no matter what.”


Make space for their feelings, whatever they may be

If the person you care about opens up, let them do the talking. Make it safe for them to express how they actually feel without trying to cheer them up or make it better. As Heen says, “When someone is hurting, and we pretend they aren’t, then we're not really seeing them. When we fail to share what's most important to us, like our feelings, we detach ourselves from others and damage our relationships.”

So attend to your friend. Pay close attention to what they’re saying and accept their feelings without judgment or advice. Acknowledge what they’re saying: “That must be awfully hard” or “It makes sense that you’d feel that way.” Chances are your friend will feel relieved that they can show their real feelings to you.


Leave your door open

As your conversation winds down, remind your friend that you’re always available to listen. They may feel support wane after the holidays, so make a commitment to be there for them in the new year and beyond. Follow up later—send a text, drop a card in the mail—and make some post-holiday plans together.

The takeaway message: Keeping your distance because you don’t know what to say makes the person struggling feel even more alone. Reaching out, even if it isn’t done absolutely perfectly, reminds them that they are loved.