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 is a unique experience. Within 5 minutes of meeting her the first time, I knew I hadn’t booked enough time. I’m not sure there IS enough time. She has as many facets as a diamond, and each are beautiful!

- David