September 30, 2025
Woman Feels Pressured to Pay for First Date, Now Seeks Repayment from Wealthy Date

Woman Feels Pressured to Pay for First Date, Now Seeks Repayment from Wealthy Date

New York, NY – A recent first date experience has left a 19-year-old woman feeling humiliated and questioning her decision to pay for both meals after her date, a man from a wealthy family, seemingly abandoned her at the checkout. The incident has sparked a discussion online about dating etiquette and financial fairness on first dates.

The woman shared her story on Reddit’s popular forum “Am I the A——?”, explaining the uncomfortable situation where she felt pressured to pay, despite the man’s insistence that he wasn’t hungry. Now, she wonders if she should ask him to repay her for at least the expensive drink he consumed but didn’t offer to contribute toward.

An Unexpected Turn on the First Date

The woman detailed how her date was planned at a food market where she expected a sit-down meal and arrived hungry. However, the man quickly suggested grabbing something quick before sitting down, ordering only a frappe while she chose a bagel. When it was time to pay, the man received a phone call and distractedly left her to handle the bill.

“The cashier ended up combining our orders, and I felt pressured into paying for both of us,” she explained. Despite the man’s earlier claim of not being hungry, he proceeded to eat half of her bagel without offering to cover any costs, leaving her feeling uncomfortable and taken advantage of.

Reactions from the Online Community

The woman’s story quickly gained traction on Reddit, prompting a wide range of responses from readers:

  • Some advised her to let go of the situation and focus on moving forward rather than pursuing repayment.
  • Others sympathized, recognizing the unfairness of her footing the entire bill on a first date, especially given her financial constraints compared to her date’s wealthy background.
  • One blunt Reddit user stated,

    “The guy is an a——. I would’ve saved the receipt and then emailed it to him requesting a payment via Zelle or Venmo. Then block his number. He’s a loser.”

Financial Pressures and Dating Etiquette

This incident highlights the pressures many individuals face on first dates, particularly regarding who pays the bill and the expectations around financial contributions.

The woman shared, “I’m not exactly swimming in cash right now — and, for context, he comes from a wealthy family — so I feel a little humiliated.”

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Experts and social commentators often recommend clear communication about payment expectations to avoid misunderstandings. In this case, the woman felt that the uneven financial dynamic on the date was compounded by the man’s lack of responsibility at the end of the meal.

For more background and similar stories, visit the original report on People.com.

What Can Be Learned From This Date?

  • Open communication before a date about payment can help prevent awkward situations.
  • It is important to recognize and respect the other person’s financial situation to avoid feelings of pressure or humiliation.
  • Trust your instincts; if a date behaves disrespectfully or selfishly, it may be best to move on.

While it’s unclear if the woman will ask her date to reimburse her, her story has sparked important conversations about fairness and respect in dating scenarios.

What do you think about this situation? Have you ever felt pressured to pay on a first date? Share your thoughts in the comments below!

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Mathew Owen

Mathew Owen is a seasoned news writer with 3 years of experience covering a broad spectrum of topics for us. Known for his keen eye for detail and balanced reporting, Mathew delivers timely and engaging news stories that keep readers well-informed. His dedication to accuracy and clarity makes him a trusted voice in journalism

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