Madison Winter (@MadisonwinterTo) header
Madison Winter (@MadisonwinterTo) profile picture

Madison Winter

@MadisonwinterTo

Your fun-loving Canadian girlfriend. Occasionally sweet. Often sassy.

 Toronto, Ontario
bio.site/madisonwinter
Joined September 2016
  • Tweets27.3K
  • Following2.1K
  • Followers225K
1.5KMedia
Photo by Madison Winter (@MadisonwinterTo)Photo by Madison Winter (@MadisonwinterTo)Photo by Madison Winter (@MadisonwinterTo)Photo by Madison Winter (@MadisonwinterTo)Photo by Madison Winter (@MadisonwinterTo)Photo by Madison Winter (@MadisonwinterTo)Photo by Madison Winter (@MadisonwinterTo)Photo by Madison Winter (@MadisonwinterTo)Photo by Madison Winter (@MadisonwinterTo)Photo by Madison Winter (@MadisonwinterTo)
Madison Winter retweeted
Gabi Ashton🌹NYC (@GabiAshton) profile picture
Gabi Ashton🌹NYC
@GabiAshtonSep 10
5pm dinner.. in bed by 9 🥰✨
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Replying to @MadisonwinterTo
We better see a #madisoninmaldives photo soon
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Madison Winter retweeted
FUESTMAN 💵 (@GregMq9) profile picture
FUESTMAN 💵@GregMq9Aug 20
If she's ignoring you, pay until she's not
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Madison Winter retweeted
Angelica Noi (@angelicanoi) profile picture
Angelica Noi@angelicanoiAug 22
It’s very possible to be a kind and caring person while having strong personal and professional boundaries and zero tolerance for disrespect ❤️
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Madison Winter retweeted
Camille Clarke (@camilleclarke__) profile picture
Camille Clarke
@camilleclarke__Aug 6
A little appetite for destruction 🤘🌹 @MadisonwinterTo
Image from Camille Clarke (@camilleclarke__)
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Madison Winter retweeted
cleo varda | (@CleoVardaTO) profile picture
cleo varda |@CleoVardaTOAug 4
Replying to @MadisonwinterTo
“Where in the world is Madison Winter” ✨
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If I ever “retire”, no I didn’t.
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Madison Winter retweeted
🌹Maya Rose🌹 (@MayaRosexx) profile picture
🌹Maya Rose🌹
@MayaRosexxJul 21
me
michael (@heatherr0ads) profile picturemichael@heatherr0adsJul 16
roommate just told me he’s “running off seven hours of sleep”
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Madison Winter retweeted
holisticbaddie (@holisticbaddie) profile picture
holisticbaddie
@holisticbaddieJul 11
I started thinking like a man all i'm worried about is my protein, going to the gym and making money
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Madison Winter retweeted
Miss Dior (@missdiornyc) profile picture
Miss Dior
@missdiornycJul 5
List of priorities in 2026: 1. Me
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Sex workers are the hardest to fuck with people you will ever meet. Incredible negotiators with immaculate boundaries. The ones who aren’t wash out. The idea that we need saving is absolutely hilarious.
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Madison Winter retweeted
Zoey (@Zoey168102) profile picture
Zoey@Zoey168102Jun 15
Normalize being very direct, very straight to the point and very assertive. A surprising amount of tension in adult life exist because people avoid saying what they actually mean.
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Madison Winter retweeted
Angelica Noi (@angelicanoi) profile picture
Angelica Noi@angelicanoiJun 15
It's never made sense to me how much SW are punished for merely existing, for using what is undeniably our most "marketable asset" by this world's standards and using it to improve our quality of life.
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Canadians are very nice people. Until they’re not. It’s best that everyone understand this now, before we go any further.
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Green flags: • believes the hotel is as important as the destination • gets you gifts without you ever needing to ask • “I booked us a spa day” • “I got us the corner booth” • has a note in his phone with your wishlist of items, hotels, experiences, and restaurants you mentioned in conversation, and he’s working through the list • has self-awareness in a public setting • never rushes you out of a place you’re enjoying • feels as cosy to your nervous system as a hotel bed • honours the daily sacred 2-3 hours of ‘each on their own’ time on vacation
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Madison Winter retweeted
Stassi Jolie (@JolieStassi) profile picture
Stassi Jolie@JolieStassiMar 22
If you love her, let her add your credit card to her apple wallet. ♥️
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Madison Winter retweeted
Gigi Lenoir CHICAGO (@exploregigi) profile picture
Gigi Lenoir CHICAGO
@exploregigiMar 9
It makes you 100x more attractive and me 100x more ready to please when you bring a gift. Sorry, not sorry.
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Madison Winter retweeted
Nithya Shri (@Nithya_Shrii) profile picture
Nithya Shri
@Nithya_ShriiMar 6
We need a law to ban talking on speaker phone in public.
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Madison Winter retweeted
Alexandra Snow (@DominaSnow) profile picture
Alexandra Snow@DominaSnowMar 3
International Sex Worker Rights Day is not a hashtag, it is a response to systems that treat our labor as profitable but our existence as disposable. So here are our demands. Not vibes or empowerment fluff, demands.
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Madison Winter retweeted
Isabella Bloom (@DateIsabella) profile picture
Isabella Bloom@DateIsabellaFeb 15
The more you develop feelings for a woman the more you should want to give to her. You shouldn’t want to give less because you fear it’s superficial or makes your love transactional. Giving her tangible things will only make it more real.
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