Source: Life 
Of all the letters you will write during your life, the sympathy note is arguably the hardest to pen. It can be very difficult to find the right words, or any words really, to say. We worry about saying the wrong thing , or we feel awkward talking about such a serious matter. It’s thus often tempting not to say anything at all. We tell ourselves that the person knows we love and support them anyway.
And they probably do. But everyone would rather hear it from you themselves. They want a tangible reminder that you are thinking about them during their hard time. Your words can bring a brief, but very real moment of comfort.
Awhile ago, Kate and I lost our baby when Kate was 6 months pregnant. Both of us were absolutely devastated. I can still tell you the names of each and every person who sent us a sympathy note. The cards brought moments of peace during that very dark time. I cherish the kindness the people who took the time to write showed us.
So the first rule about sympathy notes is to always write one. Whether you live close to the person or far away, whether you knew the person they lost well or not at all, take the time to pen them a note. It’s actually preferable to share your sympathies in a letter as opposed to bringing it up to the person the next time you see them. Sharing your sympathies in public can bring up all of the grieving person’s feelings at a time when they’d rather remain composed. A sympathy note can be read over and experienced in the privacy of one’s home.
How to Write a Sympathy Note
Use nice stationery . Casual notes can be written on whatever is handy. But the sympathy note requires something nicer. Death is the gravest of matters and your medium should reflect your respect for the weight of the situation.
Keep it short and simple. A lot of men can’t get started writing because they think they have to come up with something deep and philosophical about death, dying, and hope. While the bad news is that there’s nothing you can write to take away a person’s pain, the good news is that the grieving friend knows this just as well as you do. They’re not expecting something profound. They just want to know that you’re thinking of them and feeling for them.
Start off by expressing your sadness at hearing about the death. “I was so sorry to hear about the death of your father.”
Share a memory. There’s not much you can do to alleviate someone’s grief, but sharing a memory of the deceased person comes close. It gives the person a few moments to laugh and remember. And it warms their heart to know that others have special memories of their loved one that they carry with them. Share some of the special qualities and favorite memories about the deceased.
If you didn’t know the person your friend lost, then skip this step. If your friend lost a baby, tell them that you understand that even though your friend never got to meet their child, they’re grieving over the loss of the future they’ve been dreaming about with him or her.
Don’t try to explain the loss. If you’re a religious person, don’t offer platitudes like “This is God’s plan,” or “This is God’s will.” This might be something the person comes to believe in the future, but in the midst of their grief, the idea of God snatching their loved one from the earth is liable to piss them off. I knew a guy who lost his wife in a car accident, leaving him to raise his 5 young children alone. He said to me, “If I hear one more person say, ‘God needed her more in heaven,’ I’m going to knock them out.”
Don’t compare your loss with theirs. This is especially true if you haven’t experienced the exact same thing. If their child has died, don’t tell them how you know what they’re going through because your dog just expired last week. You’ll come off as calluous and tick them off. If you have experienced a similar loss, a reference to your ability to truly sympathize is appropriate. But don’t go on and on about how you felt during that time; the focus should remain on the other person.
Show your solidarity. Let them know that you’re thinking and praying for them. If you or your friend or family member is not religious and a reference to prayer would not be appropriate, simply say, “My heart and thoughts go out to you during this difficult time.”
Close by offering your help. Let the person know that if there is anything you can do for them or if they ever want to talk or hang out, to please let you know.
I was so sorry to hear about the death of your mother, Nancy. Your mom was always so full of life and so fun to be around. I remember when we would come home after school, she’d always be baking cookies for us, listening to her favorite Prince album and getting down in the kitchen. You couldn’t help but be happy when you were around her. She was like a second mom to me, and I loved stopping over and telling her about what was going on with my life. She always gave me the best advice, and I’ll really miss our talks.
I know how devastating it is to lose your mom. When my mom died last year, it was incredibly traumatic. I know that it seems impossible right now, but things will get better. You’ll feel a little better with each passing week. Just keep putting one foot in front of the other.
I am thinking and praying for you every day. If you ever want to talk or grab a beer, don’t hesitate to let me know.
With Deepest Sympathy,
A final note: When Kate and I lost our baby, one of my friends gave up a sympathy card that included a gift card to a nice restaurant. When we were feeling better, this allowed us to get out and spend some time together. It was such an incredibly thoughtful gesture, and I would really recommend it to others in certain circumstances.