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How to Express Sympathy in a Thoughtful Way

Wed, Feb 01, 2023

The truth is that it can be hard to know what to do or say when someone loses a loved one. We all have the best of intentions, but sometimes concern over doing or saying “the right thing” can paralyze us into doing or saying nothing. The fear of mis-stepping or saying “the wrong thing” or upsetting them further causes us not to do anything at all, which is the real mistake, in my opinion (and experience). 

Grief can be so lonely and alienating. And when those around you carry on as if nothing has happened, that makes the grief so much worse. This is certainly the case in the days following someone’s passing, but even months or years later. 

Below are three ideas to express sympathy in a thoughtful, meaningful way. They’re not complicated. They’re not grandiose. But they will make them feel loved, cared for and seen. Best case scenario? Do all three.


Write them a note. A real note. Not an email.

When my mother passed in 2009, I received handwritten notes from all sorts of people from various parts of my life. Yes, I expected to receive notes from her friends (who were in their ‘60s) and older family members. They of course grew up before the time of email and text messages. They knew how to write letters for big moments in life. It was their generation’s custom to do so. While those letters were incredibly impactful to me, the most affecting and the most meaningful were the ones I received from my family and friends my own age.

My generation was raised on digital communication; writing letters is not part of our social customs. The fact that these individuals’ sent me an actual letter expressing their sympathy and love at the saddest time of my life was a clear signal to me how much they acknowledged what I was going through, and how much they cared about me. I still have them all in a keepsake box in my closet. They’ve moved with me from apartment to apartment, across the country and now into our family home in Texas. They are my treasures.

So send a note. A real note through the mail. It doesn’t have to be long. If you’re not sure what to say, that’s understandable. Here are a couple ideas to get your wheels turning:

  • “I am so sorry for your loss.”
  • “I am thinking of you and your family during this difficult time” [you can add in praying for them too if that is a part of your way of life]
  • Share a wonderful memory you have of the deceased. There is something so powerful about memory sharing in the face of grief.

Send a gift, but please not flowers.

My mother was much loved and when she passed, the loss of her was felt all over the world, deeply. As a result, our supportive family and friends sent flowers. Our entire kitchen was filled with various bouquets of flowers.

It was simply overwhelming. We had enough to deal with in the immediate aftermath of her death without caring for the flowers in their various states of beautiful decay. Ultimately, because we were so overwhelmed by our grief, they rotted and started to stink up our house. And then we had to deal with that. 

I do not wish to sound ungrateful. We felt loved to be thought of and to have our family and friends acknowledge the gravity of our collective loss in that moment with these beautiful bouquets. I just think there are better gifts to send in moments of sympathy than flowers for all the reasons I mention above. 

When I returned to my Brooklyn apartment maybe a week after my mom died, a basket was waiting for me outside my apartment door. It was full of US Weekly, VOGUE, Twizzlers, chocolates and bath salts – basically at that time, my favorite indulgences. A dear friend had left it for me as she knew I would be returning to my “normal” life that day. 

I was one of the first of our social circle to lose a parent and no one really knew what to do (understandably), so she did this. And it made all the difference. I still think of that moment as the beginning point for this company as that basket made such an amazing impression on me during the darkest period of my life. It also created an incredibly deep level of connection with that friend. She and I are still thick as thieves to this day, even though we no longer live in the same city or see each other very often.

In sending a sympathy gift, try to err on the side of usefulness, while also acknowledging (again) what they’re facing in grief. Our Sympathy Gift Box was curated with this in mind. A wonderful benefit of a lasting gift like this is that they will be reminded of your care and love every time they see the objects and use them. It’s truly the gift that keeps on giving in that way – continued support and love. 


a sympathy gift box including book, eye pillow, candle and bath salts


Another wonderful friend gifted me a massage gift card in the immediate aftermath of my mom’s passing. Her card read “I know how busy you are taking care of everybody else, but this is a reminder to take care of yourself”. I didn’t use it immediately but I knew it was there and it meant the world to me when I finally got to lay down on that massage table and take a deep long breath. She and I are also still very close. 

Food is a great gift option too. Fresh food, frozen food, food delivery service – any sort of food that doesn’t require much organization or work to prepare.  Or, set up a meal train for the grieving, so that they can feed themselves while they take care of all the gruesome details of a loved one’s passing. Make it easy for them to nourish themselves.

Acknowledge the loss months or years later.

An old friend somehow managed to save the date of my mother’s passing in her phone when it happened and every year she texts me or calls me on that day to tell me how much she loves me and is thinking of me. It has been thirteen years now and she’s still doing it. I truly cannot put into words how much that means to me. 

Sometimes we don’t want to remind someone of their loss so we don't say anything. We skirt around it hoping not to upset them with the memory of it. This seems to be especially true as time passes. Here’s the truth – the grieving have not forgotten their loss. It’s simply impossible to do so. So instead of pretending it’s not there, I highly recommend taking that moment to connect with your loved one and, again, acknowledge what they’re going through. It might feel awkward, but that’s okay. Life is awkward, loss especially so.

The immediate aftermath of someone’s passing is a flurry of activity. Condolences are rolling in, funeral or memorial services are being planned, bereavement leave from work or school is happening… and then it all stops. And for me, that was actually the loneliest time. I had a horrible time getting “back into the swing of it” because the swing wasn't there anymore. My whole life had been upended.

And while I wouldn’t have wanted people to constantly be talking about my mother’s death all day every day, those friends and family that took a moment every once in a while to really check in with me or offer a memory of her made all the difference. I felt, simply, seen and loved when I needed it the most.


Looking for more gift ideas? Browse our sympathy collection to create your own thoughtful sympathy gift box. 

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