Photo of Madison Winter
Photo of Madison Winter

About Me

“Hello, is it me you’re looking for?” Spoiler alert – it absolutely is.

My name is Madison Winter, but my friends call me Madi!

I used to work in Asset Management, selling Mutual Funds 9-5, but a few years ago, I stepped into the world of Companionship and haven’t looked back since.

The skills that I most treasured in my Finance career, the things that made me good at what I did, have been the foundation of my success as a companion: I have always loved connecting with people in a real, honest way. Back then, that meant recalling the nuances of someone’s life and celebrating their joys and milestones alongside them. I genuinely found a huge reward in this aspect of my work.

It’s this focus on relationship-building that I bring into my work as a companion, and it is what I pour my heart into. I’m passionate about getting to know people and understanding what drives them and what makes them tick. This is why I’ve chosen to cultivate a very small circle of handpicked gentlemen with whom I know I can authentically connect on an emotional, spiritual, and physical level.

The term “girl next door” gets thrown around a lot, but sometimes the shoe fits!

I’m from a small town in Canada, and my style is definitely more relaxed than it is refined glamour. Don’t get me wrong, I love a good excuse to slip into a little black dress, but I’m most comfortable in jeans and flannel, and happiest when snuggled up on the couch with my loves – my two pugs, a good book, and a cup of peppermint tea!

Over the years, my interest in health and wellness has blossomed, and I’m often tearing up the treadmill at Orange Theory or lifting weights in my home gym. I’m definitely a foodie, and I love to explore new recipes and discover restaurants of all cuisines. But full disclosure – my absolute favourite meals include the perfect cut of wagyu or an omakase experience!

I’m sure you’re wondering what our time together might look like. My personality is definitely type-A, and my treasured clients often joke that I’m the “alpha” in the relationship. What that means is, typically, I will take the reins and curate a very special date for us to enjoy, according to your preferences, of course. I typically try to plan a day with just the right balance of adrenaline, relaxation, and private time. With that said, our time together is just that: ours. If you have something specific in mind that you’d like to explore together, I’m more than happy to let you make our plans.

Just know, I thrive on competition – challenge me at your own risk!

Challenge me on an obstacle course, at axe-throwing, or at archery tag at your peril… Or perhaps, whisk me away to a concert and watch me light up and dance the night away in a band tee. My absolute favourite bands are Def Leppard and Lynyrd Skynyrd (I definitely lean more towards music that is older than me, particularly 80s rock!). And finally, I never say no to a spa day, especially if you lure me in with a romantic couples treatment!

Unfortunately, I’m unable to visit you in the United States owing to legal constraints around my profession, but I’d love to show you around the place I call home, Toronto. If you’ve never been here before, you’ve found the perfect guide – I know all the hidden gems, from restaurants to speakeasies and even arcade bars. I hope to share them with you.

I want our time together to be something you look forward to among the madness of the modern world.

Your best-kept secret. Your retreat.
After all, we all deserve one of those.

xoxo,
Madi

You will leave a date with this smart, funny, beautiful lady with a sense of wonderment. You’ll wonder how time could have passed so quickly. You’ll wonder how your dinner tasted since you were too engrossed in the conversation to have noticed. You’ll wonder why your cheeks hurt until you realize that it’s because you were smiling so much. You’ll wonder if it’s possible to become addicted to an experience so quickly (it is!). But one thing you’ll be sure of is that you should see her again, and for longer next time.

— Jorah

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

One of the things that makes Madi unique is her ability to immediately make me feel comfortable. Any nervous feelings I may have had in the time leading up to our time together evaporated.

Madi makes me feel like the centre of attention during our time together.

Any time spent with Madi is enchanting and passes by far too quickly.

— Steve

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

Luck is on your side if you’ve gotten this far to find Madison…To label her a companion is woefully incomplete as time with Madison left my heart, body, mind, and soul-inspired and fulfilled. She is simultaneously laidback, high energy, empathetic and a muse.

— Wayne

Madison, there is no one like her. The Most Beautiful, Intelligent, Fun, Optimistic, and Wondrous Woman I have ever met. She changed my Life in the most positive, and beautiful ways. She is comforting, calm, and collective. She is once in many lifetimes in terms of experience. She leaves a nuance of wanting to see her more, and more often as well as realizing every Moment with her is the most MAGICAL Moment yet. Will definitely continue to see her. She surpasses all expectations or indecisive thoughts one may have before meeting her for the first time. She is the best. Point. Blank. Period. End of any lingering Discussion one may have or contemplate on! The BEST!

— Baz

Time with Madison is a vacation – effortless and relaxing. Laughing and flirting over dinner, you’ll be asking yourself “How can it get any better than this?” Trust me, you want to book a longer date.

— Pete

The best decision I ever made…a natural beauty, great conversationalist, passionate and caring. Takes the time to get to know you and creates an environment suited to your likes and dislikes. Spend an evening with her and you will leave wanting for the next visit!!

— Dave

Whatever time you book with Madison is never enough for the wonder that is Madison and will require another trip to see her. A stunning beauty who is funny, caring, intelligent, and exquisite. Her smile and laughter have brought great joy to me. Life is too short. . .Book the trip and see Canada's greatest attraction.

— Adam

I drive 4-5 hr to spend a couple of hours with Madison then drive another 4-5 hr back home on the same day. That is how amazing my time with her is, no amount of distance would keep me away

— Marc

Madi is a companion who personifies the girl next door and is the girlfriend that we always desired and hoped for. Once you enter her world, you will be taken aback by her beauty, warmth, and disarming charm. I was so fortunate that she said yes to my inquiries. It was one of the best decisions in my life.

— C

Our time together passed so quickly, I noticed the true effect of our date the next morning. I felt light, and happy in my body. I felt clear and calm… I still smile thinking about her—like I am right now.

— N

If you think that a date with Madison is over when one of you walks out the door, think again. Her amazing smile, that infectious laugh, the lively sparkle in those lovely blue eyes – these things all stay with you long after that door closes. And once is all it takes. Once you’ve spent time with this beautiful, smart, and funny lady, you WILL be addicted.

— Jorah

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