Man says his date asked him about ‘his finances, social status, and why he did not pay for her friends’ meals’

SINGAPORE: A man who recently returned to the dating scene after years of hiatus was stunned when his date grilled him about his financial background.

In a Reddit post titled “Dating expectations imposed on a guy or girl,” he shared that his date didn’t just ask about his job or hobbies but went straight into questions about his “finances, social status, and even why he hadn’t offered to pay for her friends’ meals.”

According to him, the conversation quickly became uncomfortable, as the woman pressed for details that felt more suited to a bank application than a first date. After the meal, she reportedly told him he “seemed too passive” because he had apparently missed certain “cues” she was dropping throughout the evening.

The man explained that this wasn’t an isolated experience. “The previous one [date] was also similar. Has there been some kind of movement where women are taught to be difficult by walling themselves in and setting a rule book to judge guys with and how they should act?”

Reflecting on his experiences, he shared that dating now feels less genuine and more performative. “I feel there’s just too much superficiality and façade required to get to know someone better,” he wrote. “I feel like I’m losing my touch compared to those I actually got to know before.”

“Why are her friends even on that date?”

Many readers criticised the man’s date in the discussion thread, with one bluntly commenting, “Insisting on paying for her friends’ meals is ridiculous. What the hell?”

Another commented that they found it rather “interesting” that, in this era where feminism and independence are celebrated, many women still hold strong expectations of men. “It feels like a contradiction,” they wrote. “Wanting full independence yet still expecting traditional roles from guys. But this is just too much—asking him to pay for her friends’ meal.”

A third wrote, “Why are her friends even on that date?? Isn’t a date like a one-on-one thing? I’m confused.”

A fourth added, “I don’t think it’s normal to ask you to pay for her friend’s meal, but I think it’s normal to ask about finances and all that stuff because, practically speaking, I’m assuming she would date you if you meet her criteria and not waste any time if you don’t meet her criteria.”

“As harsh as it sounds, dating at this age is a very practical thing, and it’s really just dating someone whom you can afford within your pay grade kind of thing.”

In other news, a polytechnic student has sparked conversation online after revealing that his parents have been pressuring him to give them a monthly allowance, even though he only earns around S$1,000 from his internship.

Posting on the r/askSingapore subreddit on Sunday (Nov 9), the student explained that ever since he started earning, he has been helping out by paying for groceries. Still, his parents continue to insist that he “owes them big time” for covering his polytechnic fees.