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A condolence letter is a time-tested way to tell the bereaved that their loved one mattered to you, that you care. The trouble is, many of us don't know what to write or worry that we

will hit the wrong note. In any situation, writing a sympathy note can be challenging. But it can be especially perplexing if you're writing in regard to someone you've never met,

such as a friend's parent or your boss's spouse. That angst can lead to procrastination or, even worse, not extending your sympathies at all. "The biggest mistake people make

with a sympathy note or condolence card is not sending it,” says Daniel Post Senning, the great-great-grandson of famed etiquette expert Emily Post, and coauthor of _Emily Post's

Etiquette, 19th edition_. “Without question, it makes people feel acknowledged, supported, held up, connected to the community.” Here are some expert tips on how to write a condolence

letter. SNAIL MAIL IS BETTER THAN EMAIL Emails pile up, and your message can quickly get buried, so it's best to send a physical note. If the person grieving is very close to you, start

with a phone call and write the letter too. “It's not an either/or. It's a both,” says Senning. A letter “says I took the time to do this for you. I wanted you to have something I

touched, that came from me, that has some of me in it." A STORE-BOUGHT SYMPATHY CARD IS FINE Craft your message on a blank sheet of stationary or a note card with a soothing image such

as flowers or a nature scene. It's fine to send a prewritten sympathy card and include a short personal note. “The simple act of sending the card lets your recipient know you care,”

says Keely Chace, master writer at Hallmark and Hallmark.com. EXPRESS YOUR SYMPATHY Start the letter with the grieving person's first name if you know them well, or put “Dear” before

their name if your relationship is more distant, or you don't know them at all. “Hi” is too casual. Then get right into the reason you're writing. “It is perfectly safe and fine to

say, “I'm really sorry your dad died,” says Amy Cunningham, a funeral director and former magazine writer who has studied the history of condolence letters and lectures on the topic.

She prefers the word “died” to “passed away” or “transitioned.” Cunningham acknowledges that the word “died” can sound blunt to some, but notes that the language of death and dying is

changing to be more straightforward. “If you're writing to somebody who is New Age and into alternative medicine and mysticism it is OK to say ‘transitioned.’ You just have to know your

audience,” she says. KEEP IT SHORT Three or four lines are enough. After you acknowledge the loss, if you knew the deceased, tell the person who is grieving how you knew them, i.e., John

and I worked together, or Susan and I were gym buddies. Then share a story, if you have one, about how they touched your life, and close it, Cunningham says.