Return to Sender: Juicy Dilemmas from the Edge of the Envelope
My Pen Pal Confessed Romantic Feelings… Now What?
Dear Maisie,
I’ve been corresponding with someone for over a year through Postcrossing, and it turned into a beautiful pen pal friendship. But in their last letter, they confessed romantic feelings for me—and now I feel totally unsure of how to respond. I enjoy writing to them, but I don’t feel the same way. I don’t want to hurt them… but I also don’t want to lead them on. What would Maisie do?
Signed,
Stamped But Not Sealed with a Kiss.
Dear Not-Sealed,
Oof. The dreaded love in the margins. It happens more often than you’d think—there’s something dangerously romantic about handwriting and wax seals. Trust me, one well-placed fountain pen flourish can undo even the most guarded heart.
But darling, here’s your compass: kindness, clarity, and no false hope.
Write back with warmth, but gently set the tone:
“I’m truly honored by what you shared—it means a lot to know our correspondence has made such a strong connection. I treasure our friendship, and I want to continue writing as friends, if that feels right for you too.”
That gives them dignity, gives you boundaries, and leaves room for the friendship to stay—or fade—naturally.
And remember: you’re not responsible for how someone handles your honesty. But you are responsible for delivering it with care.
Paper heart intact,
Maisie
Your certified emotional postage meter
My Friend Only Writes Back If I Send Gifts
Dear Maisie,
I have a pen pal who used to be super consistent, but lately only responds when I include little extras—stickers, tea, stationery, even small trinkets. I don’t mind being generous, but it feels a little transactional now. I love snail mail for the connection, not for a reward system. How do I address this without sounding stingy or petty?
Signed,
Envelope, Not Amazon Prime
Dear Envelope,
Let me be clear, my giving goddess: you are not a gift basket with a postage stamp.
It’s one thing to delight a pen pal with the occasional surprise, but if you start to feel like you’re paying rent just to receive a response, something’s gone off the rails.
Here’s Maisie’s approach:
- Pull back the extras.
Send your next letter without goodies, and see what happens. It’s a friendship, not a subscription box. - Name it kindly.
If you’re brave, add a line like: “I noticed our letter rhythm has changed, and I’ve missed the back-and-forth of just sharing words. I hope we can keep connecting—trinkets or not.” - Reassess the vibe.
If their response is cold—or nonexistent—you’ve got your answer. And trust me, it’s okay to unsubscribe from emotionally expensive friendships.
No postage due on boundaries,
Maisie
Your advocate for snail-mail self-respect
I Accidentally Sent a Postcard to the Wrong Ex
Dear Maisie,
I recently wrote a cheeky postcard meant for my current boyfriend. Nothing too scandalous, but definitely flirty… and accidentally addressed it to my ex. Same first name. I realized it too late. I am mortified. Do I write a follow-up? Ignore it and die quietly?
Signed,
Return to Sender (PLEASE)
Dear RTS,
Oh honey. This is the kind of glorious postal catastrophe Maisie lives for.
First, know this: you are now the main character in a story your ex will tell for years. Embrace it.
Second: you have two options—
- Option A: Own it.
Send a follow-up postcard dripping with humor and grace. Something like: “Well, that was awkward. Turns out my mail has a sense of drama. Hope it gave you a laugh—I promise I’m not trying to rekindle anything… except maybe my organizational skills.” - Option B: Let it go.
If the content wasn’t too revealing and you’re not worried about blowback, you can pretend it never happened. Toss a little salt over your left shoulder and carry on.
Either way, don’t let this one silly mistake eat you alive. Even the best writers mix up their address book. You’re not doomed, darling—you’re just delightfully human.
Flushed cheeks and postage peeks,
Maisie
Your flustered but fearless paper confidante
💌 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.
Submit your letter to Dear Maisie NOW!
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