“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.