Photo of Madison Winter
Photo of Madison Winter

FAQ

How do I set up a date with you?

Please send me an email introducing youself! This is a date after all! Let me know perhaps where you live, and anything else you think I should know about you. Do you have any experience in the realm of companionship? Please include your screening information, along with your requested date length in your initial email.

Or, simply fill out my booking form.

Emails that are missing the information aforementioned, or impolite, will likely not be responded to.

What information do I need to provide?

I screen not only for safety, but for chemistry. Along with an introduction, please include at minimum your name, email address, and any applicable board handles.

I will also require one of the following:

  1. A recent, reference from another independent provider,
  2. Your fully filled out Linked-in profile with photo or lastly,
  3. An unaltered, scanned piece of your photo ID.

Do you have a Deposit/ Confirmation Policy?

To mitigate against cancellations and no-shows, I require a non-refundable deposit of 25% for dates. I’m happy to apply your deposit to our next date, if it’s booked within three months, for a date anytime within 1 year. If you cancel with less than 7 days notice, your deposit will not be transferrable.

What can I expect during our date?

I’m very much a loving and tactile girlfriend. I’m particular with who I spend time with, and enjoy connecting with suitors I truly enjoy being with. I’m the type of lady who asks questions. I enjoy truly connecting with you in a way that’s natural and organic. I want to forge a friendship, a level of comfort, and establish a mutual relationship that surpasses the confines of a bedroom.

I love to start my dates with a meal, or tea, see where our time takes us. My suitors agree that time spent behind closed doors is significanty more enjoyable once we’ve had a chance to break the ice, connect as people and let our guards down. I hope that as we continue to meet, our friendship grows and evolves as we do, leaving us both longing for the next encounter.

Can I give you a gift?

Gifts are always appreciated, but never expected! E-gift cards to Mariott (I love their hotels and spas!), Air Canada, Lululemon, Anthropology, or Hotels.com always go to good use!

If you’re looking for something on the day of our date- a great bottle of red (bonus points for Pinot Noir!), kombucha, flowers, or candles are my absolute favourite.

Do you see couples or female clients? Will you see my friend and I?

While I’m super flattered, unfortunately, I do not meet with multiple clients at once, or see female clientele. I am open to joint platonic dates with other companions, however, otherwise, I am available to meet with gentlemen only.

What are your ‘stats’?

I’m 5’6 in height, and I’m 32 years old. I do have three small tattoos and only ear piercings. My photos show my figure in detail, however, I don’t believe it’s necessary to include my weight or any other sizes in order for us to have a meaningful connection.

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

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

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

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

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

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

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

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

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

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

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

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

© 2025 Madison Winter. All Rights Reserved

Handcrafted Design & Dev by Honey Butter