Something has been weighing on my heart a lot recently, and I’m really not sure what the right answer is. Maybe there isn’t a right answer. I don’t know.

A handful of my friends are very sad right now because of life circumstances. They put on a smile and they soldier on through their days, but you can see their pain behind their eyes if you look closely.

And it actually breaks my heart, because I don’t want them to hurt at all. I want them to be doing amazingly, all of the time. I know that’s naïve, but that’s what I want.

When our friends are sad, we should demonstrate in meaningful ways that we care. That we really, truly care. We should ask them specifically how “such and such” is going, and how they are doing, and how they are feeling about everything, and if they want to talk about it. We should provide wise and thoughtful encouragement that lifts them up and fills them with hope and peace. And of course, we should sit with them silently and let our presence do at least some of the talking. If they say they don’t want to talk about it, that’s perfectly fine, but shouldn’t we try? Shouldn’t we at least let them lovingly know that their situation is on our hearts and minds?

But sometimes it feels like certain topics are off-limits. Maybe because of certain social conventions. Maybe because they might make us or them feel awkward. Maybe because we are afraid we might make things worse. Maybe because it’s too exhausting or uncomfortable to go deep, well beneath surface conversations.

Sometimes it feels like certain topics are off-limits. Maybe because of certain social conventions. Maybe because they might make us or them feel awkward. Maybe because we are afraid we might make things worse. Maybe because it’s too exhausting or uncomfortable to go deep, well beneath surface conversations.

Here are some examples:

If a friend has lost their mom, whether in the last month or in the last year, we might be hesitant to ask how they are doing with the loss at this moment (whether it is a week later, or a month later, or a year later).

If a friend is struggling with not being able to have children, we might be hesitant to ask how they are doing with the waiting, and the trusting, and the ache of it all.

If a friend is struggling with not meeting anyone – not finding the love of their life – we might be hesitant to ask how their heart is handling the loneliness, and the fears, and the hope being continually deferred.

I know it’s difficult to press in and broach such difficult subject matter. I know it’s so much easier to talk about lighter, fluffier topics. But if we deeply care about the other person, and their hearts and lives truly matter to us, shouldn’t we demonstrate that by simply asking about the hard stuff?

Here’s why I think we should. Or, why I should. When I was single – for many, many years – no one ever asked me about how I was doing in that area. I would have loved to hear questions like:

How are you doing with singleness right now?

Do you ever struggle with loneliness?

Do you have a crush on anyone right now?

What type of girl are you looking for?

Do you ever wonder if you’ll ever meet someone?

I was dying for someone to ask any variation of those questions. And the fact that nobody did was actually quite damaging to my psyche, because it served to confirm my own self-doubt, self-hate, and self-pity. I saw in myself so many things that made me unlikeable and unloveable to others, and as such felt pretty hopeless that I’d ever meet someone. Well, the silence of everyone who never asked me about my singleness or relationship hopes loudly communicated to me that they saw those same things too. That they were similarly hopeless for me, hopeless that I’d ever meet someone.

I was dying for someone to ask any variation of any of those questions. And the fact that nobody did was actually quite damaging to my psyche, because it served to confirm my own self-doubt, self-hate, and self-pity.

I cannot express how much that hurt me. It probably wasn’t true, and it obviously reflected a misguided and unhealthy thought process, but that was my reality.  And the inaction of others reinforced it, and redoubled my pain.

A person can get through anything if they have hope, and I just wanted hope. I was trying so hard to muster it up for myself, and it would have helped so much if someone else would have shown they had hope for me in that specific area of my life. All they had to do was show me that they cared by simply asking me questions about it.

A person can get through anything if they have hope, and I just wanted hope. I was trying to so hard to muster it up for myself, and it would have helped so much if someone else would have shown they had hope for me in that specific area of my life.

And so I’ve come to this conclusion: my default should be to press in. At the right time and in the right place, I should ask my friend how he is doing with the loss of his dad and what he misses the most about him – even if it happened years ago. I should ask my friend how she is doing with the long delay in getting pregnant, and what is helping her to believe for the best. And I should ask my friend how he is doing with loneliness, and wanting so badly to meet the love of his life. I should go deep.

Maybe they’ve been dying for someone to ask them about it. Like I was.

Maybe it will convey that another person has hope for them and their situation, no matter how hopeless they themselves feel. Like I did.

Maybe God will use it to touch their heart, and breathe a little bit of hope back into it. Like I needed.

It could make such a difference. I don’t want to let social convention or awkwardness or fear or laziness or uncomfortableness keep me from making a difference in their lives. I want to be the best friend to them that I can possibly be.

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