In a perfect world, when you’re checking in with someone who’s struggling, you’d have your conversation together in a calm, private setting. Phones and devices would be silenced and stashed out of sight. Food and drinks tend to put people at ease, so you’d nosh on snacks or sip a beverage together, too.

But this, of course, isn’t a perfect world, and we’re still in the throes of a pandemic, so this idyllic social scenario may not be possible anytime soon. So it’s even more important you choose the right moment to check in, as it will determine the quality of the interaction you have.

While we may not be able to be physically present when we approach a troubled friend, we can create an atmosphere — and cultivate the right mind-set within ourselves — so the other person will feel comfortable opening up when they need support most.

When you chat with a friend, you should be on the lookout for noticeable changes in their demeanor, such as an irritable mood or a disheveled appearance. If your friend has recently experienced relationship issues, health problems or workplace stress, or has faced financial difficulties, they may be especially vulnerable to anguish right now.

Depending on your relationship, you might want to tread carefully. Personal friends, work colleagues, classmates and family members all require different approaches. Carefully considering the power dynamics before you approach, as it’s easier to be vulnerable with someone if you’re on equal footing.

In some cases, even asking if someone is OK, “depending on how, where and when it’s posed, could be seen as an affront or even something where a case is being built to dismiss that person,” she said. She recommends reassuring the other person that you’re asking from a place of real concern. If the person doesn’t want to engage, say you respect their decision. Assure them you’ll drop the issue.

When you check in with others, you are opening some vulnerability there and that takes some insight. So it’s important to make sure you’re in a healthy place to be present and engage with someone who’s struggling.

Be explicit: “I notice you’ve been slower to respond to my text messages.” Or, “I see you’ve been sleeping a lot more than usual. Is there anything you want to talk about?”

By indicating you’ve noticed a change in their behavior, “you give them the opportunity to either confirm what you’re saying or deny it. You’re not telling the other person how they feel, but you’re initiating a conversation and giving them a chance to address the change, she said.

If you have the kind of relationship where you can honor confidentiality, offer it. Your promise might help them feel more secure confiding in you. If there’s potential for embarrassment or shame, let the person know you understand if they’re not ready to have a conversation. Just reiterate that you care about them, which is why you’re asking.

When asking someone if they’re OK, the other person may reflexively reply they’re fine, which shuts the conversation down. Keep your questions open-ended:

“How are things?”

“Is anything on your mind?”

“What’s the most difficult thing you’ve experienced lately?”

If you are more familiar with this person, Dr. Lee suggests asking specific questions to show you care:

“How did your meeting go?”

“How are your kids adjusting to so many changes at school?”

This way, your questions come out naturally. What you’re trying to do is actually show that you want to know what their life is like and how they’re actually experiencing their circumstances.

Share a little bit about yourself to get the conversation rolling. Saying something like: “I’ve been so stressed. How have things been for you?” Or “I’m sick of cooking meals. How have you been handling staying home?” Opening the conversation this way gives the other person permission to air their own grievances and worries.

Ssending a letter or postcard to someone as a way to let them know you’re thinking about them. You could write: “I’m wondering how you are.” The phrasing leaves a lot of room for people to choose whether to engage.

When you’re in the conversation and someone is sharing with you a horrible situation that they’re going through, the first thing that most people think is, ‘What do I say? How can I help them?’”. It’s an understandable reaction but thinking about those things distracts your mind and you actually aren’t able to be empathetic.

Putting yourself in their shoes. Even if you sit in silence, your facial expressions and body language will convey your empathetic reaction. Validate your friend. Say that yes, their situation is painful. The most helpful thing that we can do for each other is just share that you’re actually burdened together.

For complex problems with no easy solutions, you shouldn’t expect that you can resolve these issues on your own. If your friend is experiencing distress, tell them to reach out to their primary care physician or family doctor for added support. If your friend is religious, encourage them to reach out to a clergy person as “they’re often really helpful with things like this”.

Coming up with a follow-up plan — a phone call in a few days, a socially distanced picnic, a Zoom call — not only gives the other person something to look forward to, but it also sends the message that this checkup isn’t going to be a one-time thing. It also takes the pressure off the other person from feeling as if they have to provide daily updates and gives you both space to process your conversation.

We don’t realize how much being seen can really change somebody’s mood. The idea that you checked in on them is telling them, ‘Hey, not only am I seen, but also that I’m known and I’m loved.’”

There will be times when your friends aren’t able to communicate what they need from you. The goal is to plant a seed so that when they do need support, they’ll know you’re somebody they can reach out to.