Her room was a mess. Papers were everywhere. Her suitcases lay open and overflowing. Her black linen dress from Morocco hung in dry cleaner’s plastic from an open closet door. “Where’s the check?” I questioned, trying to make the transaction simple. She shuffled through piles of papers, looked under clothing, and dumped out various bags before claiming to have left the check in the Tesla she’d driven back from upstate. Of course, it couldn’t be easy. Of course, there was a problem.

She called the Tesla dealership, and then her lawyer’s office. (“He must have it,” she said). I refused to leave. Anna said the check would be dropped off, so I waited. I went with her to Le Coucou, where she met with a different lawyer and a private-wealth manager. I followed her back to the lobby in the Beekman, where she ordered oysters and a bottle of white wine. I sat in silence, sending work e-mails from my phone, largely ignoring Anna, but keeping a watchful eye and asking periodically for an update. To prove a point, I stayed until 11 P.M. I left angrily, telling her I’d be back at 8 A.M. so we could go together to the bank. She agreed. “I hope you had fun, at least,” she chirped, with an impish grin. “No, this was not fun. This is not O.K.,” I stammered incredulously.

The next morning, I arrived at the hotel on time. Anna was not there. I was livid. Her overt evasion confirmed what I had feared most: Anna was not to be trusted.

Finally—why had it taken me so long?—I began to investigate on my own. I reached out to the friends through whom I’d met Anna and was referred to a guy who’d once loaned her money. He was German, like she was, and had known Anna since she lived in Paris. He told me a story that was alarming and reassuring in equal measure. He said that, after weeks of pestering, he had gotten his money back by threatening to involve the authorities, since Anna always maintained she was afraid of being deported. “Her dad is a Russian billionaire,” he said. “He brings oil from Russia to Germany.” The details obviously came directly from Anna, but they didn’t add up—Anna had told me that her parents worked in solar energy. He said that Anna had told him that she received around $30,000 at the start of each month and blew through it, and that she stood to inherit $10 million on her 26th birthday, the previous January, but because she was such a mess, her dad had arranged for the inheritance to be delayed until September of the same year, just a few months away.

I knew that something wasn’t right. I searched for a way to reach Anna’s parents, but could find none. On the week of July Fourth, while I was in South Carolina with my family (who knew nothing of the situation), I received a text from the trainer. She told me that Anna was asleep on her couch. Did she not have another place to stay? Two days later, Anna texted me, too, asking if she could stay at my apartment. I said no.

A day later, Anna called me crying. “I can’t be alone right now,” she pleaded. I offered to meet at her hotel. “I had to check out. Can I come to you?” she asked. I said no and hung up. Then my conscience got the better of me. I called her back: “You can come by, but you can’t stay here.” She was at my door within the hour. I didn’t have the energy to engage, so I said very little. My tiny studio apartment was in terrible disarray, the physical manifestation of my mental state: piles of papers, boxes, clothing, and stuff. I apologized for the mess. “You don’t need to apologize to me,” she said. She was right. I made a conscious decision to turn the proverbial cheek. I ordered two salads and put on Bridget Jones’s Diary. When she asked to sleep on my couch, I was hardly surprised.

Anna called me crying. “I can’t be alone right now,” she pleaded. I offered to meet at her hotel. “I had to check out, can I come to you?” she asked. I said no and hung up.

Even this far down the road, I tried to maintain an optimistic view of the situation: my friend had run into an unimaginable spell of bad luck; any day it would be resolved. This optimism was one of my defining characteristics, an Achilles’ heel. It’s what allowed me to befriend Anna in the first place: a willful suspension of judgment, an earnest filtration that looked for the best in others and excused the worst.