Office Hours with Professor DeMilo

Missed connections made right in Chicago

Chicago is huge but also very small.

Everyone seems to know the same everyone that you know even if our lives barely ever cross paths in meat-space. The internet makes those lines even more blurry by building parasocial relationships so deep you often catch yourself saying “oh, I know her!“ despite never having actually been in the same room together. Such is the case for myself and Gem DeMilo.

We crossed paths and exchanged glances at social outings every once in awhile, but for some reason or another, we never had a chance to make the time. We both were in a deep, committed relationship with the Windy City but never actually hung out until we independently packed up and moved across the country.

I found myself in Philadelphia. While Gem, on the other hand, chose a locale a bit more rustic and bucolic: Asheville, North Carolina. But her sense of wanderlust never relented and during a visit to Philly we at last found the stars aligning.

A long overdue fated meeting over Manhattans, raw oysters, and cat pics in an Old City bar took place. At the time, I was so new to the city that I had to ask her, who has never been a local, for resto recommendations. I don’t want to say that’s when history was made, but we connected as if we’d known each other for a long time. Between our POVs on intimacy, our excellent taste in art (if I do say so myself…), our insatiable appetites for adventure, it was a meeting that was certainly worth waiting for.

And now, we find ourselves reconnecting all over again where both of our stories began: Chicago.

If you haven’t heard the news, Gem is back in Chicago

I’ll let her take it from here ⬇️

“I wasn’t expecting to return to Chicago so soon, but I’m happy to be back in my one true home

After less than three years away, I find myself back in Chicago once again. Life has a way of throwing you curveballs, and a category 4 hurricane hitting Appalachia certainly was the curviest ball I could ever imagine. While it was a difficult decision to make under very difficult circumstances, I couldn’t be happier with this reunion with my hometown, the city by the lake and broad shoulders. One thing this experience has taught me more than anything is that true connection knows no bounds. Wherever life takes you and whatever life throws at you, your people will remain your people, and Max is undoubtedly one of my people. My friendship with Max began when we were taking a chance in life in our own ways and establishing our new respective homes. And now we reconnect again in the city that started everything for both of us in our own separate ways, bringing it all full circle.

The universe has a beautiful sense of humor, doesn’t she?”