Open When Letters for Your Best Friend: 25 Ideas and Sample Notes

Hi. I don’t know what happened today, but it was bad enough that you opened this, so: I’m sorry. You can tell me the whole story without making it entertaining or finding a bright side. For now, make the tea in this envelope. Put on the softest thing you own. Text me one word that sums up today, and I’ll reply with something stupid. You don’t have to turn this into a good day before you’re allowed to be done with it.

Hi, night owl. No need to write back. I wish I were there to talk about something extremely unimportant, like what we’d name a sailboat we’d almost certainly never learn to sail. For now, this is a small hello in the quiet. You don’t have to figure out your whole life before morning. Get as comfortable as you can. We can talk tomorrow.

I would like to enter something into evidence. Remember when you [one real thing she did, even though it was hard]? I do. I remember that you weren’t sure how it would go, and you did it anyway. I’m not saying everything is easy for you. I’ve seen how much effort some things take. That’s part of why I believe in you. You don’t have to feel confident for any of that to be true. Borrow my opinion of you for a little while.

I’m so sorry. You’re allowed to miss them, be angry, feel relieved, or cycle through all three before lunch. You don’t owe me a tidy explanation. I won’t make you list their faults to prove you’re better off, and I won’t rush you toward someone new. I can listen to the same story again. What happened in this relationship doesn’t settle the question of whether you’re lovable. I’ve known you a long time. That question isn’t up for debate.

If I could, I’d sit next to you right now and say nothing especially wise. We’d probably end up talking about dinner. I know this letter can’t replace having someone there, but I want you to have a reminder that you can tell me the unpolished version of how you’re doing. Or we can talk about something completely ordinary. Send me a picture of whatever’s in front of you, if you feel like it. I want to see your view.

This is a formal invitation to be very unimpressive today. Wear the same comfortable clothes. Watch something you’ve already seen. Please don’t clean up before letting anyone help you. I put a little soup money in here because I’d rather be arriving with a container of it. If you need something picked up or someone to listen to a detailed account of how miserable you feel, ask me. No cheerful reply required.

I know what today is. You don’t have to talk about it, and you don’t have to spend the whole day being sad, either. I just didn’t want the date to pass without telling you I remember. I remember [a small, specific thing about the person or pet she lost], and how much you loved them. If you’d like company, I’d be glad to make a plan. If you’d rather have the day to yourself, there’s no need to explain.

Shoulders down. Unclench your jaw. (I know.) You don’t have to feel fearless to do this. You can pause before answering, ask a question, or take a second to collect yourself. Whatever happens in there, it won’t be the whole story of who you are. I’m rooting for you, and I want the play-by-play afterward—not just if it goes well. Go take the next step.

I won’t pretend I know the answer from inside an envelope. Try telling me what the choices actually are, what matters most to you, and what each one would cost—in time, money, or energy. If a piece of information is missing, you’re allowed to go get it before deciding. If it’s a small choice you can undo, maybe it doesn’t need another three hours of your evening. Call me if you want a sounding board. I can listen without casting the deciding vote.

You don’t have to look blameless for me to love you. If you want my honest opinion, tell me the part you’re tempted to leave out, too. I’ll listen, and I’ll tell you what I really think—not just whatever will make this conversation easiest. If you owe an apology, I’ll help you find the words. If you need help, you don’t have to make a perfect case before asking. Being your friend doesn’t mean agreeing with you about everything. It means I care enough to pay attention.

This envelope is a permission slip. You are hereby excused from folding the laundry, answering nonurgent messages, and making tonight useful in any measurable way. Anything that can safely wait is invited to wait. You do not have to get one more thing done before sitting down. Signed, me. I will not be asking what you accomplished.

AHHHH. I don’t even know what it is yet and I’m already yelling. Before you move straight on to the next thing, please take a minute to enjoy this one. You don’t have to make it sound smaller when you tell me. I want the excited version, with the unnecessary details and the part you keep repeating because you still can’t believe it. Pour something fizzy if you have it. Then send me an inappropriately long voice memo.

Happy birthday to my favorite person to text about absolutely nothing. Another year of you is good news for everyone who knows you, and especially for me. Here’s what I want for you this year: one real adventure, one lazy Sunday that turns into a lazy Monday, and at least one moment when you catch your reflection and think, “Oh, she’s doing great.” I hope there’s something in this year that surprises you in the best way. I’m very glad I get to hear about it.

Well, hello. Look at you, smiling at your phone. I want everything: how you met, what they said, the tiny detail you’ve already told someone twice. I’m so happy there’s someone you’re excited about. Mostly, I hope you can be yourself with them, and that they’re as interested in knowing you as you are in knowing them. Also, please tell me their name before I accidentally refer to them as “the phone-smile person” in public.

Before you rush on to whatever’s next, notice what you just did. There were days you weren’t sure you could get through this. You kept going anyway, sometimes clumsily, and clumsy still counts. I hope you have a little room to breathe now. You don’t have to turn the whole experience into a lesson or tell me it made you stronger. I’m just glad you’re here, on this side of it. I’m so proud of you I could embarrass us both in public.

Hi, it’s me. I put a picture of us in here. Look at us. That’s still us, even when we’re in different places and our schedules are being deeply uncooperative. I miss the conversations that start with something important and somehow end with us looking up whether penguins have knees. Send me a voice memo, even if all you have to report is what you’re making for dinner. I miss the ordinary stuff, too.

A few things to picture for no important reason:

• A goose chasing a grown man across a parking lot.
• Someone saying “per my last email” out loud, in person, with a straight face.
• A dog in a raincoat looking furious about both the rain and the coat.
• Us trying to tell a story and making each other laugh before we get to the point.

Now send me the worst joke you know. I am prepared to lower the standard further.

Bored? Excellent. I made you a menu. Choose one:

• Send me a voice memo reviewing your lunch like a dramatic food critic.
• Find an old photo of us and recreate both our poses by yourself.
• Choose three songs for the soundtrack of a movie about your day.
• Draw a portrait of me without lifting your pen from the paper.

I especially want to see the portrait. Accuracy is not encouraged.

I wish we were having this conversation in person, but I don’t want to skip the part where I listen. When you’re ready, tell me what happened and what I haven’t understood. If I’ve hurt you, I need to take responsibility for that—not point to a sweet letter and ask us to move on. You don’t have to pretend we’re fine to protect my feelings. I care about getting this right, not just getting back to normal. Take the time you need.

Do you remember the road trip when we got lost for two hours because you refused to use your phone? You “had a feeling” about that exit. Your feeling was wrong. We ended up eating gas station nachos on the hood of the car while the sun went down, and it’s still one of my favorite nights ever. I love that we can have a whole argument about directions and then sit there happily sharing terrible nachos. If I have to be lost somewhere, I want it to be with you.

No reason. Nothing’s wrong. I just wanted you to have one envelope that isn’t about a disaster or a celebration. So: hi. I like you. I like how you text in all lowercase when you’re tired, and how you always know what song is playing in the grocery store. I like that I can tell you a story with no point and you’ll still have questions. Have a perfectly ordinary day. I’m glad you’re in mine.

First night. The light switches are in the wrong places, and the thing you need is almost certainly in a box labeled something unhelpful. You don’t have to make this feel like home tonight. Find your bedding, eat dinner wherever you’ve managed to clear a spot, and put one familiar thing where you can see it. I’d love a video tour, including the boxes. I’m excited to learn the little details of this place with you.

Packing list: phone charger, comfortable pants, sense of humor, this letter. I hope there are plenty of good parts—the food you missed, the familiar stories, someone being genuinely thrilled to see you. And if you need a break from all that togetherness, you can take one. You can love people and still want an hour to yourself. Send me the holiday highlights whenever you have a quiet minute. I am particularly interested in the dessert situation.

Hi, future you. I’m writing this on [today’s date], and right now you’re [a brief snapshot of her life]. I wonder whether things worked out the way you hoped, or whether something else became more important along the way. Whatever has changed, I hope there’s still room for the things you love doing just because you love them. I also hope we’re still telling each other stories that require far too much background information. Write me back if you feel like it. I want to hear what this year was actually like.

Last envelope. I don’t know how long it’s been or which of these letters you needed most. I hope a few made you laugh, and I hope the hard-day ones felt like company. Mostly, I wanted this one to say thank you. Not just for the big moments, but for being the person I get to tell about the small ones. I’m grateful for you. The letters are finished. We aren’t.