How to Ask if Someone’s Okay (Even When They're Not)

You've probably heard it before, maybe seen it on your social feed, or even hummed along to Jessie J's tune, or followed a K-Drama echoing the sentiment.

It's okay not to be okay.

How do you know if someone’s not okay?

It's tricky, because not everyone wears their emotions on their sleeve. However, if you pay attention to subtle changes—like their appearance or demeanor—you might pick up on the signs.

But here's the catch: assumptions only get you so far. To really understand what someone’s going through, you've got to ask.

Asking might seem straightforward for others, but it's an art. Because, sure, anyone can ask questions; but asking them in a meaningful way takes knowing what to ask and how to ask it.

If asking isn’t done properly, some people won't share their experiences or feelings openly. The goal is to create a space where they feel at ease expressing themselves—a task easier said than done.

So, before initiating a conversation with someone, it's wise to take a pause to consider a few key points; because casually asking "Are you okay?" might not have the positive effect we hope for, as it could catch them off guard and make them feel uneasy. Here are five tips to help you ask if someone's okay—even when they're not.

1. Pick the Right Moment. When you're planning to have this talk, anticipate that it will get a bit serious or heavy. Conversations like this need the right time and place. Like what was mentioned earlier, asking if someone’s okay shouldn’t be a spur-of-the-moment thing. Make sure both of you aren't busy so you can focus. Also, find a spot where there aren't too many people around. It's even better if it's just the two of you. That way, the other person won’t feel bombarded when you start the conversation. Their emotions might already be all over the place, and you definitely don't want to add to that. So, picking the right moment is crucial.

2. Rephrase and Probe. The question, "Are you okay?" has become too ordinary. Often, people reply with a quick "Yeah," or turn the question back on you, asking, "Why'd you ask?"

It's important to rephrase it or ask questions that encourage a genuine response. Instead of yes-or-no questions, try asking more open-ended ones.

Stephanie Harrison, a happiness expert and author of "The New Happy," suggests these alternatives:

a. "What’s been on your mind lately?"

b. "What question do you wish someone would ask you right now?"

c. "What’s feeling good, and what’s feeling hard?"

d. "How are you doing right now?”

e. "The last time we talked, you were dealing with [X problem]. How has that been lately?"

f. “What word would you use to describe your life right now?”

g. "If you were being completely honest with me, how would you describe your feelings lately?"

Even if we rephrase, don't expect them to pour their heart out immediately. It's important to keep probing or use follow-up questions. They can help clear up any ambiguities or bring us closer to understanding their true emotions. For instance, if they mention struggling with school or work, you might ask, "How has that been affecting your day-to-day?"

3. Listen to Understand, Not to Respond. Stephen Covey, known for his bestselling book "The Seven Habits of Highly Effective People," once pointed out that we often listen with the intention of responding rather than truly understanding. You've probably caught yourself mentally preparing your reply while someone else talks. Don't worry, it happens to the best of us! But it shouldn't become a habit.

People do this for various reasons. Some feel pressured to respond because they think the person confiding in them chose them for a reason. Some fear forgetting what they want to say. And some see it as a way of showing they're paying attention. However, to practice empathetic listening, we need to let go.

Covey advised us to put aside any urge to reply during the conversation and focus solely on listening. When thoughts of responses arise, ignore them. Instead, wait for a natural pause in the conversation to respond. You might not say much, but that's alright, because you're prioritizing listening. Plus, moments of silence can be beneficial for everyone to reflect.

4. Ask and Speak with Care. Asking questions can sometimes feel like an interrogation; but when it comes to checking in on someone's well-being, we want to avoid making them feel like they're being grilled. If we don't ask them with care, it might seem like we're just prying into their personal lives.

Speaking with care on the other hand means being reassuring. Let them know that you appreciate them opening up, even though it's tough to admit when things aren’t going well; that you empathize with their struggles and understand how hard it's been; and that you're there to lend an ear or a hand whenever they need it.

Choosing our words carefully is essential because reassurance can sometimes appear as toxic positivity. This form of positivity includes statements such as “Everything happens for a reason,” that may seem helpful in the moment but can ultimately lead to false assurances in the long run. So, while offering support, remember to strike a balance by avoiding dismissive or overly optimistic responses.

5. Prepare Yourself. Sometimes, we overlook our own well-being while caring for others. You might not even realize it, but you could be feeling off too. Take a moment to assess your own emotions and make sure you're in the right headspace to start this conversation.

Take note: empathizing with others starts with empathizing with yourself. It's like putting on your own oxygen mask before helping others on a plane. Take care of yourself first so you can offer genuine support to someone else.

In our culture, we're often praised for our resilience as Filipinos; but there are moments when we're just worn out, struggling to keep going. Keeping emotions bottled up is like a volcano ready to erupt at any moment. Be the one who gives them the courage to let the pressure out.

Pay attention to those around you. You never know who might be longing for someone to ask them how they're doing. Asking holds more power than others might think, because it's through these questions that people begin to realize and accept it’s perfectly okay not to be okay. 


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