It’s after the holidays, or you let a friend down, or your mother-in-law’s beloved great-aunt died. These are but three situations in which you might need to say Thank you, I’m sorry, or I’m sorry for your loss. And yet many of these tough-but-true sentiments leave many of us tongue-tied.

Thank You

There are two main types of thank you notes, professional and personal. Some experts stress the sales pitch opportunity of the thank you. Sure, but don’t get ahead of yourself. Thank you for their time, for their consideration, for their insight into the greatest challenges facing nonprofits today, for their thoughtful questions that gave you an opportunity to reflect on how important sustainable agriculture is to you. Whatever. The point is to really say: Thank you. Then knock yourself out fixing an answer you flubbed or adding thoughts that flew out of your head in the moment. Remember that post-job interview isn’t the only time to say thanks. Thank the people who agree to let you “pick their brain” (essentially unpaid labor); thank the assistant who consistently gets you the most-wanted lunch reservation in town; thank everyone who helps you along your winding professional path.

In a personal thank you, make it actually, you know, personal. Let’s say Aunt Sally gave you the wedding present of your dreams. Tell her what you first hope to serve on those Royal Copenhagen plates. Mention how beautiful she looked in her chiffon dress, floating around the dance floor with Uncle Bob. Share your observation that the sight of them smiling and swaying to “I Get A Kick Out of You” reminded you why you wanted to say these vows in the first place. It’s also nice to end on a forward-looking note, like how you can’t wait to celebrate their upcoming 50th anniversary with them in style.

I’m Sorry

Like “thank you,” the essential element of an apology is, well, the apology. Don’t start off with an excuse, “I’m sorry, but…” or something that sounds defensive. If you’re here to apologize, then do it. “I owe you an apology, Tina.” Then, you have to own your mistake by making it clear what you did and why it was wrong. “Asking John out the day after you broke up was cruel, selfish, and wildly insensitive. It also flies in the face of my most dearly held values of friendship. Ovaries before brovaries.” Acknowledge the pain you’ve caused them, and take responsibility for your actions. “I can only imagine how betrayed you must have felt. I take full responsibility for my reprehensible behavior and the pain I have caused you.” Express your hope that your relationship can be restored to a healthy and trustful place, but don’t outright ask for forgiveness, experts say: “This places demands, whether you intend it or not, on a person whom you have already wronged. It is better to express what you really want, which is for the two of you to interact in a better way in the future.”

Condolences

There may be no other life event that causes greater loss for words than death. It happens often enough — and with such reliability! — that you’d think we could get it right. Our biggest obstacle, one funeral director recently noted, is our own ambition. “I think we want it to be too good and too all-encompassing,” she said. She shared some literary wins and losses at a workshop on writing condolence letters.

“This is not a good letter, Charlie,” Ernest Hemingway wrote to Charles Scribner, the son of his late publisher. “But I still feel too sad to write a good one.” Pros: honesty and completion.

“No one can better appreciate than I can, who am myself utterly broken-hearted by the loss of my own beloved husband, who was the light of my life, my stay, my all, what your sufferings must be,” wrote Queen Victoria to Mary Todd Lincoln after the death of the President. Cons: Making it about you.

Tell a story about the person you’ve lost, or share a memory. Offer to help; better yet, get specific.

“I was so grateful when people said, ‘Let us know if there’s anything we can do.’ a widow wrote. “But when people offered specifics, it felt even easier for me to take them up on their offers. One friend wrote, “If you ever want to come over, we can grill and make grapefruit mojitos; we’d love to see you and there’s nothing we wouldn’t do for you.”

Whatever you do, don’t resort to platitudes, cliches, or religiosity. To the bereaved, the loss of their mother/love of their life/child isn’t in God’s plan, nor did it happen for a reason. Don’t say you know how they feel, either. Even if you suffered a similar loss, all grief is unique.

Say only what is true: That this sucks so bad. That you wish you knew what to say. That you will never forget the excitement on their beloved’s face on baseball’s opening day. Have your kid draw them a picture. And if it’s someone you’re close to, don’t consider it over and done once you’ve written the note. Continued acknowledgment of the long road of grief, in a text message, a phone call, a bouquet, can be a tremendous comfort to the bereaved.

“When it seems like the world has gone on and that nobody remembers, and nobody cares,” Barbara Bouton, who worked with bereaved families for more than two decades at a hospice in Louisville, Ky., before joining the National Hospice and Palliative Care Organization, told The New York Times, “it can mean a lot just to say, ‘Hey, I remember; I care.’ “