iiinova — where your digital self keeps evolving

Gem DeMilo 🎂 October Birthday 🎉 @gemdemilo.bsky.social · 11h

I am officially down 45lbs. I’ve felt ambivalent about saying anything publicly about this. I know that in the age of GLP-1s and heroin chic/early 2000s super skinny culture making a comeback, discussing weigh loss publicly can be especially fraught....

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Gem DeMilo 🎂 October Birthday 🎉 @gemdemilo.bsky.social · 29/09/2026

Not to sound conceited, but I think I’m gonna look so hot in this set 🤩 Thanks for the lovely birthday gift, J! 💜

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Gem DeMilo 🎂 October Birthday 🎉 @gemdemilo.bsky.social · 22/09/2026

This whole iced coffee debate just makes me grateful to have a non real job.

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Gem DeMilo 🎂 October Birthday 🎉 @gemdemilo.bsky.social · 21/09/2026

Would you be OK with a jeans and t-shirt kind of date? 🤍

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Gem DeMilo 🎂 October Birthday 🎉 @gemdemilo.bsky.social · 16/09/2026

Can’t wait to see my beautiful friend @readyforrene.bsky.social next week in DC! We make such a bootyful pair 😉🍑

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Gem DeMilo 🎂 October Birthday 🎉 @gemdemilo.bsky.social · 15/09/2026

This makes me so happy 🥹. Deborah Vance is one of the most complex, intelligent, compelling, well written, brilliantly portrayed TV characters to ever exist, male or female. Congratulations on your very well deserved 5th Emmy, Queen Jean 👑

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Gem DeMilo 🎂 October Birthday 🎉 @gemdemilo.bsky.social · 09/08/2026

Your ray of sunshine ☀️

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Gem DeMilo 🎂 October Birthday 🎉 @gemdemilo.bsky.social · 26/08/2026

Dolly Parton immediately followed by Tim Curry? Can I leave this timeline please 😔💔

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Gem DeMilo 🎂 October Birthday 🎉 @gemdemilo.bsky.social · 25/08/2026

Took a little social media/email break as I had a friend in town immediately followed by a 48 hour rendezvous. Getting back to emails tonight and tomorrow 🩷

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Gem DeMilo 🎂 October Birthday 🎉 @gemdemilo.bsky.social · 19/08/2026

As a general rule, I don’t respond to inquiries with incomplete or incorrect screening information. I state my requirements simply and plainly on my site. If someone doesn’t care to read them or thinks they don’t need to follow them, they don’t warrant my attention. Simple as.

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Gem DeMilo 🎂 October Birthday 🎉 @gemdemilo.bsky.social · 06/07/2026

Do you have an affinity for voluptuous glutei maximi, and are you unable to utter a fabrication? 🖤

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Gem DeMilo 🎂 October Birthday 🎉 @gemdemilo.bsky.social · 03/08/2026

When you celebrate your birthday with @missdaffnie.bsky.social & me, just know you’re getting ALL the cake 🎂 Thanks again for an amazing night C, and HBD 🥳🎊🎁

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Gem DeMilo 🎂 October Birthday 🎉 @gemdemilo.bsky.social · 29/07/2026

As much as I love collecting Michelin stars in the West Loop, there is something very special about exploring what Chicago’s other neighborhoods have to offer too ✨ Thanks again for an amazing dinner, A 💋

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Gem DeMilo 🎂 October Birthday 🎉 @gemdemilo.bsky.social · 24/07/2026

I can’t wait to go a-frolicking in a meadow in this dress 🌸💐 Thanks for the lovely gift, J 🩷

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Gem DeMilo 🎂 October Birthday 🎉 @gemdemilo.bsky.social · 09/06/2026

How to make an entrance: a case study

Gem wears a strappy black corset and garter, her stunning figure framed in the doorway

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Josie Qu 🏡 CHI @meetjosiequ.bsky.social · 30/06/2026

My pup is recovering smoothly from her knee surgeries and removal of her mast cell tumor 💕🙏 She is my sunshine so I’m glad I had a rain day fund! However, the $7.5K was more than I anticipated 😭 If my boyfriends want to take care of me by taking care of this bill, I would be forever grateful!

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Gem DeMilo 🎂 October Birthday 🎉 @gemdemilo.bsky.social · 20/07/2026

Having a great skin day. Just thought you’d like to know 💙✨

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Gem DeMilo 🎂 October Birthday 🎉 @gemdemilo.bsky.social · 17/07/2026

There’s a content creator who’s been referring to my fair city as “Chicago Marie Illinois” and I don’t know why but it just makes sense to me that Marie is Chicago’s middle name.

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Gem DeMilo 🎂 October Birthday 🎉 @gemdemilo.bsky.social · 15/07/2026

The face I make when you tell me your worst (best) dad joke 💙

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Gem DeMilo 🎂 October Birthday 🎉 @gemdemilo.bsky.social · 10/07/2026

I wrote a little something on Substack about consent, eroticism and a viral voice memo 🧡 open.substack.com/pub/gemdemil...

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Gem DeMilo 🎂 October Birthday 🎉 @gemdemilo.bsky.social · 09/07/2026

Don’t be afraid to make mistakes. Mistakes are often our best teachers once we let go of shame and regret. Showing ourselves humility, grace and compassion is what transforms mistakes onto immeasurably valuable lessons 🌸

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Gem DeMilo 🎂 October Birthday 🎉 @gemdemilo.bsky.social · 06/07/2026

Do you have an affinity for voluptuous glutei maximi, and are you unable to utter a fabrication? 🖤

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Alex Astor ✨ FMTY 🥂 Birthday Girl 🎂🥳 @alexastorpnw.bsky.social · 25/05/2026

If you have an unpredictable schedule and are unable to confirm a date until last minute, consider pre-screening accompanied by a small gift. So, when you reach out last minute, you’re more likely to be taken seriously and met enthusiastically rather than being perceived as low-quality traffic.

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Gem DeMilo 🎂 October Birthday 🎉 @gemdemilo.bsky.social · 03/07/2026

Have you remembered to check your spam folder recently? 💖

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Rose Dubois @rosedubois.bsky.social · 02/07/2026

Always a treat to see my favorite Chicago beauty ✨ @gemdemilo.bsky.social

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Gem DeMilo 🎂 October Birthday 🎉 @gemdemilo.bsky.social · 29/06/2026

It’s a get naked and hang out by a hotel air conditioner kinda day 🥵

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Gem DeMilo 🎂 October Birthday 🎉 @gemdemilo.bsky.social · 28/06/2026

I think spending all day cooking Ina Garten’s recipes and watching John Waters movies counts as a Pride celebration.

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Gem DeMilo 🎂 October Birthday 🎉 @gemdemilo.bsky.social · 17/06/2026

Kinda upset I’m not in Boston right now. I could use more men in kilts in my life 😢

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Gem DeMilo 🎂 October Birthday 🎉 @gemdemilo.bsky.social · 17/06/2026

The midwestern urge to take an impromptu trip to the upper peninsula in Michigan to go berry picking 🍓🫐

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Gem DeMilo 🎂 October Birthday 🎉 @gemdemilo.bsky.social · 12/06/2026

They say big boobs are back in now. My question is who else was blissfully unaware that they were ever out?

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Gem DeMilo 🎂 October Birthday 🎉 @gemdemilo.bsky.social · 08/06/2026

One of the upsides of the specific niche I occupy in this industry is that I am is that I’m too boring for Forbes or The New York Post to ever write anything about me 💖

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Gem DeMilo 🎂 October Birthday 🎉 @gemdemilo.bsky.social · 05/06/2026

It’s biphobic to not have a threesome with me and one of my hot friends during pride month, just fyi 🩷💜💙

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Gem DeMilo 🎂 October Birthday 🎉 @gemdemilo.bsky.social · 05/06/2026

Newsletter finally went out, a few days later than expected. Accept some butt as a token of my apologies for keeping you waiting 💖

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Gem DeMilo 🎂 October Birthday 🎉 @gemdemilo.bsky.social · 27/05/2026

I’m officially back from Europe I and have a few ideas on how we can celebrate my return to Chicago…💛

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Gem DeMilo 🎂 October Birthday 🎉 @gemdemilo.bsky.social · 19/05/2026

See ya later, alligators! 🐊 I’m off to a little R+R in Europe. See you later this month 😘

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Gem DeMilo 🎂 October Birthday 🎉 @gemdemilo.bsky.social · 14/05/2026

Hands down, my favorite part of spring is the scent of lilacs wafting through the air 🪻💜

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Sarah J. Jackson @sjjphd.bsky.social · 10/05/2026

Like every Mother's Day today I am asking that you consider a donation to @nationalbailout.bsky.social to help free mamas who are separated from their families by the injustices of pretrial detention systems. secure.actblue.com/donate/freeb...

secure.actblue.com

Donate to #FreeBlackMamas

With your generous support we are able to continue to bail out community members, provide life-changing supportive services and resource groups who are organizing to transform the criminal justice sys...

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