Gems From Gem DeMilo
Just a humble little newsletter containing up to date touring information, exclusive offers and musings from Chicago's favorite redheaded companion
- Indexed issues, last 90 days
- 3
- Latest publication
- Sep 29, 2026
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- Earliest in this view
- Jul 10, 2026
Latest issues
Falling Into My New Normal 🍂🍁 (opens the original)
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The Gains in LosingI’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. I certainly don’t mean to make anyone feel bad about where they are with their weight or imply that everyone must lose weight. However, I have also put a lot of consistent work into becoming a healthier version of myself, and I do think that’s worth celebrat
Summer Lovin' + Fall Frolics with Gem DeMilo 😎🍁 (opens the original)
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I must admit something here. I announced taking a tour hiatus for summer quite a few months ago and it left me feeling a bit nervous. What if Chicago doesn’t come through? What if I need to pick up touring sooner than I want to? What if I get restless and just have to hit the road again?Nevertheless, I stuck it out. And man, has it paid off!Not only have I been able to discover and enjoy so many different things to do in The Windy City, but I have been privileged enough to see such lovely people
Meditations on Consent, Eroticism and a Voice Memo (opens the original)
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In case you are not privy to the viral voice memo in question, the long and short of it is a man sent this voice memo to a woman after their first date as they prepared for their second, saying that he would like to have sex on the second date, and, if she is not up for that, he does not want to continue seeing her. I am actively using the most objective language possible here, but this is a direct link to the voice memo in question to provide the fullest context available:<div class="tiktok-wra
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