In Their Prime: Why Experience Is the Real Luxury
In Their Prime: Why Experience Is the Real Luxury

Thoughts from Cupid’s Escorts There’s a quiet shift that happens as people get older. Confidence settles in. Self-awareness sharpens. The need to impress fades, and the ability to connect deepens. At Cupid’s Escorts, we’ve long believed that women who are 35+ — experienced, self-assured, and fully in their prime — bring a kind of ease and […]
Cupid’s Discovers… Texting
Cupid’s Discovers… Texting

Yes. In the year of our lord early-2000s technology, Cupid’s Escorts now accepts texts. For years, Jillian resisted. She trusted phones. Voices. Real conversations. The sacred art of actually calling. But eventually, after much persuasion, gentle pressure, and several people saying “you know everyone texts now, right?”… Jillian has done it. She has embraced the […]
Cupid’s Escorts: The Only Agency With Its Own Holiday
Cupid’s Escorts: The Only Agency With Its Own Holiday

There are escort agencies… and then there’s Cupid’s Escorts. Most agencies operate quietly in the background of romance. Cupid’s, on the other hand, accidentally became a cultural institution. When your name is Cupid, Valentine’s Day isn’t just a busy weekend—it’s our holiday. Not metaphorically. Literally. Valentine’s Day Is Cupid’s Holiday Every February 14th, the world […]
The Women Who Leave… and the Ones Who Find Their Way Home
The Women Who Leave… and the Ones Who Find Their Way Home

A love letter to ladies who have returned to Cupid’s after many years away: There’s a unique kind of magic that happens when time passes and people return. At Cupid’s, we’ve seen it again and again: women who worked with us years—sometimes decades—ago, stepping away to live full, complex lives… and then, one day, circling […]
The Birth of the Lingerie Super Studio
The Birth of the Lingerie Super Studio

How Chaos Became Architecture Some people see mess. Some people see disaster. Jillian sees raw material. Chapter One: The Pile It begins, as all legendary problems do, with a sentence that lands like a grenade: “Uh… Jillian? None of this is organized.” She turns. Two hundred lingerie sets. A mountain of lace, mesh, satin, straps, […]
Jillian vs Toronto Traffic: A Full Moon, Four Major Games, and Construction
Jillian vs Toronto Traffic: A Full Moon, Four Major Games, and Construction

There are nights in this city that test patience. And then there are nights that test faith in reality itself. That night was not a normal night. That night was: A full moon A Raptors game A Maple Leafs game A TFC game Construction. Everywhere. All at once. Which, for anyone running logistics in Toronto, […]
Jillian vs The Early Period: A Booking Emergency
Jillian vs The Early Period: A Booking Emergency

There are phone calls that make you brace yourself. There are phone calls that make you sigh. And then there are phone calls that make you immediately say: “Oh no. Ohhh no. It’s one of those days.” This is the story of one of those calls. The Call It’s mid-afternoon. The schedule is tight. The […]
Sex Workers’ Rights — From Inside Cupid’s
Sex Workers’ Rights — From Inside Cupid’s

At Cupid’s, we don’t speak about sex workers’ rights in theory. We speak about them in practice. We have spent decades operating inside this industry — through changing laws, shifting public opinion, online speculation, moral panic, and moments of genuine progress. And if there is one thing experience teaches you, it’s this: Sex workers are […]
What the Stripper Index Says About the Economy (and What Cupid’s Escorts Sees From the Front Lines)
What the Stripper Index Says About the Economy (and What Cupid’s Escorts Sees From the Front Lines)

When economists want to understand the health of the economy, they look at stock markets, employment rates, consumer spending, and housing data. But there’s another indicator — one that rarely makes the headlines, yet has quietly predicted recessions, booms, and consumer confidence for decades. It’s called The Stripper Index. Yes. Really. And at Cupid’s Escorts, […]
History of slang: Blow job
History of slang: Blow job

An oral history   I can’t remember exactly when I first heard the term “blow job”, but it was one of the earlier ones to pass through my gentle ears. From the prudish to the worldliest, everyone knows what it means. But everyone has the same questions: “why ‘blow’”, and “why ‘job’?” Not long ago, […]