Madison Winter Madison Winter

About Me

Photo of Madison Winter

Hello there, glad you found me. My friends call me Madi.


Let me tell you a little bit about myself.

I joined the world of companionship about three years ago, promptly leaving my 9-5 in Asset Management. I thought I’d eventually return to the finance world, but as the years unfold, I’m beginning to discover just how much I love what now I do.

One of the things I was most passionate about in my prior corporate life was relationship building. Although at the time, I sold Mutual Funds, I loved connecting with my clients in a real, and honest way. I made a point to remember their birthdays, spouses’ names, pet names, children’s graduations, and other milestones. I genuinely enjoyed and found this element of business extremely rewarding.

Little did I understand at the time, how much my role as a companion overlapped.

Photo of Madison Winter
Photo of Madison Winter

“I’m beginning to discover just how much I love what I do.”

Now, I structure my business exclusively around relationship building. I prefer to meet with a small, selective handful of gentlemen with who I can truly connect on an emotional, spiritual and physical level.

I describe myself frequently as the “girl next door” and that’s for a few reasons. I’m originally from a small town, and my style is usually more relaxed & comfortable than refined glam. I’ll throw on a dress every now and then, but more often than not, I’m donning denim and some sort of flannel.

I have two pugs that are the absolute loves of my life, and I usually listen to music a few decades old. Def Leppard & Lynyrd Skynyrd are my all-time favourites. I’m a salsa dancer, and frequent backpacker, often finding myself in remote parts of the world sleeping under the stars.

If you’re wondering how our time together might look, well — that’s up to us!

Photo of Madison Winter
Photo of Madison Winter

My painfully Type-A personality and background in event planning often result in a certain organizational initiative. My treasured clients jokingly refer to me as the ‘Alpha’ (which, quite frankly, I love) because I have a habit of taking the reins and running.

Unfortunately, for legal reasons due to my profession, I am unable to visit the United States. However, I’d love to invite you to visit Toronto. If you’re unfamiliar with my city, you’re in luck. I know of all the hidden gems… restaurants, speakeasies, and arcade bars.

Depending on your preferences, of course, I try to plan a day of mixed adrenaline, relaxation, and private time.

I should warn you — I’m very competitive. Obstacle courses, ax-throwing, archery tag? I’m open to suggestions too! Either way, you can expect things to get hilariously messy. Although contrarily, I’m an absolute sucker for a couple’s day at the spa.

Think of me as your best-kept secret. I want to be something that you look forward to every so often… This is our time to sneak away from the ever-growing list of demands life throws at us.

Your time with me should be a retreat. After all, we all deserve those.

Photo of Madison Winter

Madison has one of the best reputations in the community. Her name is first to the lips of sex workers literally everywhere when the conversation turns to who might be a joy to spend time with, who is a genuine, amazing human being, or whose presence makes you a better person just by knowing them. That reputation creates high expectations. When you meet her, she exceeds all of them.

- Ben