Darling ones,
October is my favorite autumnal month! It is a month of costumes and play. October is the season of smoke and mirrors, of masquerades and mischief, of alter egos waiting in the wings. Let’s be deliciously incognito, toeing the line between truth and trickery.
We’re playing with disguises, not to hide, but to be our truest selves. The world behaves differently when it doesn’t know your name, your role, your history. And so do you.
Remember that feeling you had as a kid when you would play-act? You could be anything or anyone. I loved to be Peter Pan or Atrayu from the Neverending Story. I would pretend that Narnia was in the back of my closet. That feeling is still in you. Let’s let it out to play.
The Masquerade Mindset
I have a very dear friend, who usually acts pretty reserved at parties. She is cordial, very intelligent, and witty. She likes a fancy cocktail in a proper glass, not beer in a solo cup. She is not the guest that gets out of control or does anything wild. However, one night she put on a horse head mask as a joke and danced her ass off. She was moving and grooving—a sexy horse with gyrating cabaret hips. She even twerked! Everyone cheered. Everyone loved it. She was a star! With the mask on, she was able to be fully in her body without worrying what anyone thought. The mask gave her permission to play with wild abandon. When she took off the horse head, her face was flushed with a childlike joy.
The mask enabled her to be her true self.
A mask doesn’t conceal—it reveals. Slip one on and suddenly you can flirt with the stranger across the room without worrying if you’ll blush. You can laugh louder, dance harder, or say the thing you’ve been biting back. A mask is permission.
My partner and I are attending a Halloween party this year. He will be a lion tamer, and I will be the untamable lion. I can’t wait! Since my persona is the untamable lion, I can do whatever I want. Drink from people’s glasses, dance on a table, pretend to cough up a hairball, roar at people (or purr). I’m going to be untamable!
Here’s a secret: you don’t need October or even a literal mask to practice masquerade. Try an alias at the café. Wear lipstick so unlike your usual shade it feels like armor. Hide behind a pair of ridiculously large sunglasses. Introduce yourself as “Esmerelda” at a party and see who believes you. Play.
Because here’s the truth, my sweets: sometimes the truest version of you shows up only when you’re pretending to be someone else. The persona you invent when you’re “in costume” is not a falsehood. It’s a compass pointing toward your hidden truths. Maybe your alter ego is a seductress with a low laugh. Maybe she’s a daredevil who says yes before thinking twice. Maybe he’s a charmer who doesn’t ask permission before taking your hand to dance.
When you put on a mask or a costume, you are playing a role—so you can finally act like yourself.
.
Play with this. Trust it. Because the versions of yourself you try on for fun might just be the most authentic of all.
Gathering Idea: The Masked Mischief Supper
Invite friends to a dinner where everyone must show up in disguise—mask, wig, alter ego, whatever tickles their fancy.
Rule one: Stay in character through the first drink, or through the appetizers, or until dessert. It’s your dinner party, so go with what feels fun to you.
Rule two: Your alter ego has one outrageous skill or secret (they can levitate spoons, they’re heir to a mysterious fortune, they once seduced a magician, they are heir to a multi-billion dollar cantaloupe export company).
Speak in a voice that isn’t yours.
Tell outrageous stories about your “other life.”
Flirt, swagger, pout, sparkle—whatever your mask demands.
Rule three: Anyone who “breaks character” before dessert (or time you have chosen) has to do a cheeky dare.
You’ll be astonished how freeing it feels to meet your best friends all over again. Play keeps us young!
Advice Column: On Being Deliciously Deceptive
Q: Isn’t deception…bad?
A: Darling, we’re not talking about tax fraud. We’re talking about play. Deception as a spark, a costume, a tease. It’s about writing your number on a napkin and signing it “The Countess.” It’s about swapping name tags at conferences. It’s about letting yourself step outside the roles that cage you.
Perhaps your romantic partner needs to meet Esmerelda, the temptress who only wears red and speaks with an accent?
A little playful deception won’t harm a soul. In fact, it might save one. Yours. Remember, play keeps us young.
Special Mischief Assignment and a Cocktail Recipe for Paid Subscribers
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