Running an Airbnb in Chicago has its stories—but none quite like the lady from New York.
She messaged us saying she needed a place to stay because her lover had just died. Grief is heavy, so of course, we showed compassion. She booked the room and stayed for a few months. Each morning, she’d wake up, put on her shades, and head to the movies. She always said she was looking for a job and trying to start over.
The rent here is under $700, and we allow some flexibility—but not confusion. Still, she would pay in random pieces. $200 here, $150 there. The rent is due between the 1st and the 5th, but she’d always have a new excuse. She told us stories about shelters, abuse, a degree, and that she speaks fluent Spanish and French.
But after a while, I told my brother, “She’s been doing this all her life. Working the system.” It wasn’t about the rent. It was the pattern—the stories, the delay, the performance.
Advice? If you're hosting, have a clear agreement and trust your gut. Compassion is beautiful—but don't confuse survival stories with scams. Boundaries keep everyone safe.
Question for You: Would you have let her stay, or asked her to go?
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