DIY Open When Letters (with What's Inside!)

Updated: Oct 5, 2020

Originally published: 3/22/2018

It's a week before your best friend’s birthday, and you still haven't gotten her a present. Not only are you unsure of what to get, but you also can’t remember how much money you have left in your bank account.

The Dilemma: You want to be cute and creative, but the ideas you find online seem too difficult or involved, and you honestly don’t have the time. So, you go on and continuously browse the internet, wasting more of that "precious" time, and find nothing.

✋Let me make it a bit easier for you.

My solution is DIY Open When Letters. This crafty gift trend has taken Pinterest by storm. By no means is this a new thing, but there are so many examples that don’t give enough detail about what to put inside!

Let’s first define what “Open When’s” are for those that may not have heard of the concept.

Definition: O•pen When Let•ters noun 1. a bunch of letters given to someone as a present all at once, each defining a moment when the recipient should open a specific letter. “Open when you’re happy”, “Open when you need a break”

Last year I made these letters for my sister and boyfriend for their spring semester. Both go to college away from me, so it was a great present idea that they really enjoyed throughout their semesters.

Unlike other Open When posts you might find, I am going to show you all of the letters I made for them with a description of exactly what went inside each.

There is no template or package you need to purchase—it just takes some creativity.

Don’t think you have to be some amazing artist, either! You can just title each letter without all the doodles, or you can design the covers on your computer and print them directly on the envelopes.

Here are the Open When letters I made with details of what goes inside.


Open When...

1. Right Now

  • For: BF & Sis

  • Included: A letter that explains what "Open When's" are and what the rules were (Yes, I spelled "lose" wrong)

2. You've had a Bad Day

  • For: BF & Sis

  • Included: a funny letter (I did my favorite the Office quotes) and funny pictures I knew they would enjoy

3. You're Sick

  • For: BF & Sis

  • Included: a Get Well card, tissues, and a little band-aid cartoon to make them smile

4. You Miss the Pup

  • For: Sis

  • Included: a letter from our dog signed with her painted paw print (it was too coveted for me to get back for this pic) and pictures of the pup

5. You're Annoyed with Me

  • For: BF

  • Included: a generic apology letter with reasons why he likes me and I like him:)

6. You Need a Laugh

  • For: BF & Sis

  • Included: a letter full of 20 inside jokes sure to make them laugh and funny, embarrassing photos (Pictured was for Sis)

7. You're Bored

  • For: BF & Sis

  • Included for BF: Sudoku and a letter retelling a special moment in our relationship

  • Included for Sis: Sudoku, coloring pages, corny magazine clippings, and a letter retelling of the days when she supported me during my HS theatre days (Pictured)

8. It's Valentine's Day (for Sis)

  • Included: a Vday note with funny/cute valentines I found online and tween magazine cutouts

9. It's Valentine's Day (for BF)

  • Included: One of my corny, hand-drawn pun cards

10. You're Stressed

  • For: BF & Sis

  • Included: Funny memes and a letter that included a link to a personalized Spotify playlist I made for each of them

11. You Miss Me

  • For: BF

  • Included: a letter with some of the best moments in our relationship, some pictures of me, and a card with my perfume

12. You Feel Homesick (for Sis)

  • Included: A note and pictures of the fam that would make her smile

13. You Feel Homesick (for BF)

  • Included: a note, pictures with his fam, and coupons for the Wendy's that we went to A LOT in high school

14. You Need to Know How Much I Love You

  • For: BF

  • Included: a note, a list of 10 subtle reasons why I love him, and pictures of moments/memories that made me love him

15. It's the Day Before Your First Game

  • For: BF

  • Included: a good luck letter since I couldn't be there and relevant pics (one that was from my first time at one of his HS games)

16. You Can't Sleep

  • For: BF & Sis

  • Included: a letter with an explanation of what I do when I can't sleep and good memories to clear a busy mind along with some photos (Pictured was for BF)

17. You Need a Hug - PROBS MY FAV

  • For: Sis

  • Included: a picture of us hugging, and, get this, my hands traced, cut out, and attached to string with a note instructing her to wrap the hands around herself--a "mailable" hug. So funny.

18. You Feel Like Giving Up

  • For: BF & Sis

  • Included: a letter of encouragement and relevant pictures that show support

19. You're Taking Finals (for Sis)

  • Included: a note, Smarties, and a picture at the beach to show summer is not too far away

20. You're Taking Finals (for BF)

  • Included: a note and gift card for food during finals week

If there is anything you takeaway from this post, know this:

The amount of effort you put into these letters is noticed and appreciated. It is truly a gift that keeps on giving for months, as if each individual letter is a present in itself.

The letters definitely take some time to make—I think it was 3 days in total for me. I hope that by giving you this inspiration, it can knock off a day of planning for you. I suggest working on it when you need a break from school or want busy work to pass the time.

Although time-consuming, I thoroughly enjoyed making each letter.

My greatest bit of advice is to just have fun, and don’t take it too seriously! Some of those letters definitely didn’t look “Pinterest worthy,” but they were meaningful and personal.

So, go for it! Show someone how much you care for basically no cost to you.



The feeling your best friend gets opening your letters…priceless :)

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