Sure, love letters are fun to send when your sister is pregnant, your aunt got a promotion and your college roommate just finished grad school. But what about the friend who lost her brother, your mother-in-law who just spent way too much time in the hospital or that neighbor struggling through a hot mess of a job loss?

Here's the truth: It's hard to know what to say when things are hard. 

I find myself sitting over a blank notecard, trying to write the "right" message. The fact is there really isn't a right thing to say, but I have a few tips.

1. Be Honest
   Emily Post and I agree on this point. Just "say what you truly feel." 
2. Keep it Brief
   We do not want to dwell on the bummer, so let's keep our message to our saddened friend honest (as we just discussed) and concise. Shoot for 3-4 sentences of kind-hearted words.
3. Don't Try to "Understand"
   We've all experienced pain. We've all been through a break up, a break down or an arm break, but everyone experiences despair in their own way. I know it's tempting to say "I totally know what you're going through" (and believe me I've done it more times that I would like to admit). As humans, and ones who feel enough empathy to send notes in the mail, we are inclined to relate to each other, but in this case, let's just be supportive and leave the "understanding" to a IRL conversation. 
4. But Offer Specific Support
   Close your note with a specific, personal offer. "I know it won't mend your broken heart, but I'd love to bring over some wine and a hug soon." 
5. Grief Has No Expiration Date
   Yes, it's important to send a timely note. Any of us who have lost someone we loved, suffered through an illness or dealt with any kid of heaviness, well, we know that there's no absolute end date for the pain of it. You had a hard time putting into words what to say to a friend who is suffering? Send a note now. People say "it's the thought that counts" for a reason. Because it's true. If you send a message from your heart, it'll be heartfelt.

I've pulled together some of my favorite cards for those hard-to-say situations below.
Click on an image to take you to the home of these super talented, thoughtful greeting card makers.