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Illustration by Danielle Davis

When a venture capitalist invited Jane Dinh, an entrepreneur in San Francisco, out for a second date a couple years ago, he had an unusual question for her. Would she be interested in pretending to be homeless with him for a night?

The venture capitalist, whom Dinh met through a dating app, told her he wanted to see if he could “live with less” just in case an investment fund he planned to raise imploded, said Dinh, who declined to name the venture capitalist. Her curiosity piqued, Dinh agreed to the date, which consisted of the two of them eating fast food and sleeping in a tent they pitched in a neighborhood park in San Francisco. 

“It was like urban camping, but he was just labeling it as being homeless,” said Dinh, who later founded an online travel company. 

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