Getting ready for another trip to Seattle Feb 16th-20th. Get on my dance card while you still can.

Passed the barre today

Just saw an ad for a "beautiful mid-evil Tuscany getaway". When I behave wickedly, it's always top shelf.

"“…your cleverness and double/triple entendres has me seduced from a thousand miles away…" -- Mr. L

"I've only ever been with submissive women. I'm not into any whips or chains or any of that, but I like that you seem very...assertive." Indeed.

A glimpse into my inbox: “After reviewing your prospectus and digital media assets, I have found the opportunity to step into your office to be quite intriguing. I am confident that setting up a strategic partnership with you and...

Can't stay away from the Emerald City! I'll be visiting Seattle Feb 18th-21st. Get on my dance card while you can!

“You had me at ‘return on investment’.” I’ve always been a romantic.

"You are both a luxury and a necessity." -- Mr. SF

To my date 13 years my junior, this one's for you

Luna della Lupa. Celebrating the Wolf Moon.

Required reading

Rewarded Secretary with a friend. 4 peas? Really?

New year, new account. Follow all my 2026 adventures www.instagram.com/milehigf/

Excerpt from my origin story post, working title No Man Knows My History: “At a research conference, I had the good fortune to sit by a fascinating older woman. She offered me chocolate (I liked her instantly). She revealed she was a retired anthropology professor working as a dominatrix...

Hot off the press

Getting in the mood. Get in on the Office Playlist - Las Vegas Edition open.spotify.com/playlist/57h...

Preparing my 2026 travel itinerary. Where should I go?

Ms. York is kicking off 2026 at CES in Las Vegas Jan 6th-9th. Get on my dance card while you can.

What's Ms. York's favorite New Year's tradition? Winding down the year right with one last executive coaching session. Happy New Year!

"I’ve realized that I want to see hockey-stick growth too—in our relationship."

Making new friends on the Gram. Come say hi! @ milehigf

What can you say during sex but also at a philosophy dinner?

I just learned about adult content protection apps called Covenant Eyes and Net Nanny. Those would make for excellent gangster names.

I could really go for a Negroni right now. No, I'm not talking about the drink.

Another Xmas present

Christmas in Colorado was supposed to be about skiing. Here I am picnic planning.

"Merry Christmas, ya filthy animal"

Sign in the powerlifting gym: "Do NOT cook fish in the microwave". Wise words.

Self-portrait. I call it "The Nutcracker".

Just received my invite to a Deck the Balls party to raise testicular cancer awareness. Will you be my date?

One of my core competencies

Doing some Winter Solstice shadow work this morning.

Join the office holiday party

A popular adult site just released its yearly review. Older women and office rendezvous are occupying a lot of fantasies. Can confirm.

When I set out for the party, I did not realize I would come home with a new Monty Python monologue to memorize. Ask me on a date and I might give you a taste.

Have you heard Ms. York's Office Playlist? The soundtrack to power your productivity. msyork.substack.com/p/office-pla...

Future Madeline is thankful

Looking at the forecast today. Chicago, your status as the Windy City is in jeopardy.

Xmas came early this year

Him: "I'm sorry I called you a pervert at the party." Her: "In that crowd? I take it as highest praise."

Never thought I'd say this in December. Unseasonably warm weather has me planning a Xmas picnic.

I do love when a man plans in advance - 3.5 months in advance to be precise.

Sick of seeing AI generated "high end" life. For 2026, I'm leaning into real, authentic, and genuine. Brace yourselves for pictures of authentic bedhead and my messy desk.

Helluva Sunday School lesson this Sabbath morn. I'm at a sexual health conference atm. Just heard the proctologist speaker say "go and spread the anal gospel".

Lady date: "You seem so innocent. With your little dress and cute voice." Ms York: "I love the element of surprise."

I'll be celebrating the holidays Icelandic style this year. Xmas Eve is called Jólabókaflóðið, or "Xmas Book Flood". They exchange books and eat chocolate.

New subscribers to the Executive Newsletter will receive my pitch deck to download for free. 💌 www.meetmadelineyork.com

"¿Tienes una lista de deseos?" Yes, indeed I do have a wishlist. Pimsleur subscription just added. I have quite a bit of travel lined up for 2026. Ayúdame a aprender español.