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The story behind

What started as a box of heartfelt notes from friends and family on a milestone birthday turned into a life-changing reminder of the power of words. On good days and hard days alike, those letters were a tangible manifestation of love. Now, Rainy Day Love Letters helps others create that same kind of lasting connection, crafting bundles of encouragement, joy, and love to be opened whenever they’re needed most.

  1. Words matter!

  2. What people are really craving is connection.

  3. Simple gestures can change someone's day— or their life.

  4. Every moment is a chance to say, "you matter to me."

Rainy Day Love Letters began with a gift that wasn’t about things. It was about love.

We believe:

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On my 48th birthday, my dear friend Sally Ann threw me a party. I had asked for no presents—at this stage of life, I didn’t need more things. But Sally Ann had something special in mind. Instead of gifts, she had party guests and out of town family write heartfelt letters for me.
She gathered these beautiful messages in a wooden box and presented them to me. I remember holding that box and feeling the weight of not just paper, but love—real, personal, thoughtful love from people who matter most to me.
I wasn’t sure what to do at first. Should I read them all that day? Or should I save them for later, for a time when I might need a little boost? I decided to read just a couple right then, and the words in those letters filled my heart in a way no gift could.
A month later, on a particularly difficult day, I spotted the box on my shelf and decided to open it again. As I read through more letters, it felt like each one was a lifeline—reminding me of the love I’m surrounded by, even when life feels overwhelming. Those letters lasted me through the year, and they became the best gift I’ve ever received. I didn’t need more stuff; I needed those words, that connection, that reminder of the people who love me.

And like my dear friend Sally Ann did for me, together we’ll make sure the people who matter to you never forget how loved they are.

As my next birthday approached, I found myself lying in bed, thinking about how special that experience was. I wanted more of those letters. I was even trying to craft a Facebook post in my head, asking people to write them for me again. That’s when the idea hit me—wouldn’t it be amazing if there were a service where people could create and gift love letters, not just for birthdays but for all kinds of occasions? A wedding, a graduation, the birth of a baby, or even a random Tuesday when someone could use a little encouragement.
That night, at 2 a.m., I impulsively bought the domain and email address for what would become Rainy Day Love Letters. The concept was simple but powerful: A way for people to give the gift of love and support through heartfelt letters, written by those who care most. Whether for a birthday, a challenging time, or just because, these letters could become a treasure chest of encouragement for someone to pull from on their hardest days.
Since then, the idea has grown. I’ve envisioned different ways for people to participate. The essence, though, remains the same: it’s all about connection. Rainy Day Love Letters is here to help you celebrate your loved ones or even to gift yourself a bit of encouragement on life’s stormiest days.
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