I've recently been seeing these "Open When" letters all over Pinterest and Tumblr. They're basically envelopes that you open when the topic applies to you. For example, "Open when you're sad" would be opening if you're not really having a good day and need to be cheered up. Inside each "Open when" envelope, there's something inside that is supposed to apply to the topic. These "Open when" envelopes are absolutely adorable, so I figured why not make them? I'm 90% sure that these are meant to be given to significant others, but since I don't have one, I made these to give to a friend. As I was making them, the biggest issue that I had was trying to figure out what to put inside. All of those Pinterest posts only show the envelope decorations, but they don't tell me what's inside. So I've decided to share what I filled these envelopes with if you're feeling stumped with what to fill them with. 

DIY "Open When" Letters | Sunny Rebecca

Filling the envelopes

"Open me now."

The first letter should contain instructions for opening in the letters. I put some rules in there, such as that you can open a maximum of one letter per week, mostly because I wanted to space out the usage of these letters. I also wrote any other information that I needed the receiver to know so that they understand how these letters work. 

"Open when you need a favor."

Remember when you were little and you made little coupon cards for your parents to use, like "free hug" or "No chores?" That's essentially what I put inside this envelope! Using the Meri Meri Paper Love Tokens as inspiration, I made little ticket cards that can be redeemed to receive different things. I included, "Lunch date" and "Free Starbucks hot chocolate," that the receiver can redeem from me. This is your chance to personalize these coupons to fit the person. While the love tokens that you can buy from stores are absolutely adorable, you can save money and make them personalized by making them yourself. I used cardstock and some markers, and then cut them into the shape of tickets. 

"Open when you're sad."

I filled this envelope with hot chocolate packets, but you can put other things, like tea bags or stickers in there, something to cheer the receiver up. Some other ideas of things that you could put inside might be chocolate.

"Open when you've had a great day."

I filled this envelope with confetti, which I made using a hole punch, colored paper, and glitter. I put the confetti in a plastic bag to be sure that it wouldn't leak out. Basically, what you can put in here can be anything that would celebrate a great day. When you have a great day, it's possible to make it even better, so fill the envelope with things that will do just that. It's time to celebrate, because it's a party in this envelope!

"Open when you need to love yourself."

Sometimes, we forget how awesome we are and need someone to remind us how great we are. I filled this envelope with ten things that I love about her, so that on a day that she feels like she hates herself, she can remember how fantastic that she truly is. It's kind of like 10 Things I Hate About You, but it's the opposite. 

"Open when you're feeling sick."

Sick days are the worst. But what if you could make them just a tiny bit better? I filled this envelope with a few things. A pack of tissues labeled, "for your nose," a tea bag labeled, "for your throat," a picture of us labeled, "for your heart," and some band-aids labeled, "for where it hurts." You can also fill this envelope with other things to help them get better, like cough drops or vitamins. 

"Open when you're bored."

This could span a few potential gifts, I put a short story that I wrote about a girl that became friends with a dog. You could put word searches, crossword puzzles, links to funny YouTube videos, something that they can do to pass the time. 

"Open when you need some encouragement."

Ever have those days where nothing seems to go right? This envelope has one of those "take what you need" tear off flyers. If you don't know what I mean by that, it's basically a sheet of paper, but you can rip off the things that you need, like "hope" or "courage." Kind of like those flyers where you can take someone's number from by ripping off a tab, this flyer has traits that someone might need to cheer up.

DIY "Open When" Letters | Sunny Rebecca

How to decorate the letters

I had so much fun decorating the letters, I found most of my inspiration on Pinterest. there are some really creative letter designs on there, a lot of the ones that I did are from there. Basically, it's best to use a mix of different fonts. Try capital letters, cursive, lower case, big letters, small letters, spaced out letters, condensed letters, thin letters, fat letters, short letters, tall letters, there are tons of ways to create different fonts with your handwriting. Experiment with mixing different font designs, because the style of font can make a huge difference in terms of design. 
You can also use a mix of lines, arrows, banners, leaves, dots, and other doodles to make the envelope a bit more fancy. I personally love the mountain design (which I found on Pinterest) and the banner designs. Don't worry if your drawing isn't great, because the point of these letters is to look handmade, kind of like doodles. 
I chose to decorate both the front of the envelope and also the tab where you open it. I would write when to open the letters on the front and then on the back, I would write a little message that related to the topic. For "You should open me now," the back corresponded with the same colors and says, "Your adventure begins now." Similarly, the letter that reads, "For when you need to love yourself," has "because Justin Bieber wasn't lying" on the back tab. 

DIY "Open When" Letters | Sunny RebeccaDIY "Open When" Letters | Sunny Rebecca

DIY "Open When" Letters | Sunny Rebecca

I think that the best thing that you can do while making these "Open when" letters is to just have fun with it. Decorating these letters was so much fun, I got to be creative and artistic. It also feels great to make these for someone else, thinking about how they would react when they opened each envelope and how to help with whatever they're going through. You can make these "Open when" letters for a friend or a significant other, anyone that is important in your life. It's a great creative gift to give to someone that's incredibly thoughtful or even just a nice gift to remind a someone how much you love them. If you do end up making these "Open when" letters, I would love to see how they turned out! Feel free to tweet them to me so that I can see them!


  1. These are so cute, Rebecca!! I've seen these all over Twitter, but I've never gotten to hear about what people put on the inside, so I loved being able to see what you included in each one. Your ideas were so creative!

    xo, Alison

    1. Glad that you liked these ideas! I noticed the same thing about how people never revealed what was inside and half of the fun is seeing what you get when you do actually open the letters, so it's SUCH an essential part!