‘Mama you have 370’: NYC woman went on a few dates with a guy she really liked. Then he sent her an unexpected request

After a few dates, a woman from NYC said she started to think this one might actually go somewhere. Then came a text that changed things.

Anna, who posts under her name on TikTok, recently shared a story about a guy she had been seeing that quickly drew reactions in her comments section. According to her account, the two had gone on several dates and she was genuinely into him, describing him as someone she thought was really cute. That is, until he sent her a message asking for money on Cash App.

“I’m so sad cause this boy that I thought was really cute that I went on a few dates with, started asking me for money,” Anna said. She said the request was pretty direct. “Just straight up started asking for $370 on Cash App,” she explained, adding that he later clarified what the money was for. “And at the end, he says that he needed it for a flight.”

The issue was never just about the money

For Anna, the issue was not really about the amount. It was what the ask seemed to say about how he saw her. “But my thought process was like, wow, you think that lowly of me that you asked me for money?” she said. She went on to explain that, hypothetically, he would have been one of the last people she would ask for financial help. “Like, even if I really, really, really needed money, like, people were after me, the last person I would ask is like, this boy that I have a crush on.”

For some people, money conversations early in dating can reveal a lot about a relationship. In another viral dating story, a woman’s joke about getting money from her dad after her card declined on a Taco Bell date was enough for the guy she was seeing to question their future together.  

Anna later shared where she stands with the guy who texted her. “So he definitely does not give a rat’s ass about what I think about him,” she said.

Anna’s comments section quickly filled up with people sharing their own versions of similarly awkward money asks. “I genuinely can’t comprehend a man asking for money like are u serious,” one commenter wrote, drawing over 13,000 likes. 

Another commenter shared, “A man asked me for $250 once for pokemon cards so he could resell them.” A different commenter kept it short, simply noting, “We in hell” in response to the growing pile of similar stories underneath Anna’s post.

It is worth noting that Anna’s story, as she tells it, does not include any indication of whether she actually sent the money or how the conversation with him ended beyond the ask itself. Her focus was less on whether she sent the money and more on what the request suggested about his intentions.

For Anna, the bigger issue was not just the $370 request, but what it suggested about the person she was getting to know. That kind of concern has shown up in other viral dating stories too, including one woman who said her boyfriend asked her for $400 before; she later questioned the reason he gave for needing it. In Anna’s case, she said the request alone was enough to make her rethink the connection.

Stories like these tend to strike a nerve online partly because they touch on a familiar early-dating worry, that a new connection might be more about convenience than genuine interest. For now, Anna’s post is another example of how quickly a small moment in dating can become a bigger conversation online.