The Paper Trail of Advice for the Hopelessly Handwritten
Dear Maisie,
I love sending postcards and handwritten letters, but I never know what to write beyond “Hope you’re well!” I freeze up every time. How do I write something that feels heartfelt or interesting without sounding awkward or like I’m trying too hard?
Sincerely,
Tongue-Tied in Tennessee
Dear Tongue-Tied,
Oh darling, if I had a postage stamp for every time someone wrote “Hope this finds you well”, I’d have enough to mail myself to Paris in first class.
Let me tell you a secret: interesting writing doesn’t come from trying harder—it comes from loosening the corset of perfection.
Instead of reaching for what’s appropriate, reach for what’s true. Here are three little tricks to un-knot your tongue and give your postcards a pulse:
- Write like you talk—just with a wink.
Imagine telling a friend, “Today I saw a dog wearing sunglasses and it changed me.” Now that’s a postcard opener. - Get sensory.
Describe something around you: the color of the sky, the smell of your coffee, the weird mural you pass on your walk. People love feeling like they’re stepping into your moment. - Ask better questions.
Instead of “How are you?”, try:- “What’s the most curious thing you’ve seen this week?”
- “If your mood were a color today, what shade would it be?”
- “What book should I pretend I’ve read but secretly haven’t?”
Lastly, give yourself grace. Not every card has to be profound. Sometimes a well-placed doodle and a quote from a bathroom stall are all it takes to connect.
So go ahead—write boldly, messily, and without apology. There’s magic in the margins.
Stamped with affection,
Maisie
Your inky confessional companion
Dear Maisie,
I’ve been writing letters to a pen pal for over a year. We had a great connection—deep conversations, funny doodles, even the occasional poetry exchange. But for the last few months, her replies have gotten shorter and colder. I still send thoughtful letters, but she barely responds. I’m heartbroken. Do I stop writing? Ask what’s wrong? Ghost the ghoster?
Signed,
Languishing in Letters
Dear Languishing,
Oh sweet envelope-hearted soul, nothing stings quite like being ghosted via snail mail. That’s a slow ache with no tracking number.
First things first: breathe. You are not alone. Every great letter writer has at least one story of the epistolary fade. Sometimes it’s burnout. Sometimes life gets loud. Sometimes—brace yourself—it’s just the end of a season.
But Maisie doesn’t believe in vanishing without grace. So here’s what you do:
- Send one more letter—short and open-hearted.
Something like:
“I’ve noticed a shift and wanted to check in. If life’s gotten busy or you need a pause, I understand. I’ve really valued our exchanges and just wanted to say thank you.” This gives her room to respond (or not), while letting you close the loop with dignity and intention. - Resist the urge to pour your hurt into the mailbox.
I know you’re tempted to write a 7-page manifesto with a dramatic flair (believe me, I’ve been this close to including pressed rose petals and teardrops), but don’t. Preserve your energy for those who write back with warmth. - Remember: her silence does not diminish your words.
You wrote with love. That energy lingers, even if it didn’t return.
Now pour yourself some tea (or whiskey, I don’t judge), light a candle, and write a letter to someone new. The world is full of pen pals who will write you back with fire and feeling.
Forever sealing envelopes with soul,
Maisie
Your postal patron saint of emotional clarity
💌 Got a juicy dilemma, a heart that’s heavy, or a neighbor who won’t stop playing the kazoo at midnight?
Whether it’s a love note gone sideways, a friendship fading into static, or just life being life—Maisie wants to hear it all. From heartbreaks to green bean drama, she reads every letter like it was written in fountain pen on perfumed stationery.
📬 Write it down, seal it up (metaphorically), and let Maisie sort your mess with elegance, edge, and envelope-worthy advice.
Your secrets are safe. Your sass is welcome. And your story? Deserves to be heard.