Woman says she's ‘bewildered' after man asks her to 'PayNow him' for their first date dinner

Independent Singapore

2 days ago

SINGAPORE: A woman was surprised when a man she went on a first date with asked her to send him money via PayNow for dinner, several days after they met.
She shared her experience on the r/askSingapore forum on Saturday (May 31), explaining that she had agreed to meet the man, who is in his 30s, after they had developed a good connection through their conversations on a dating app.
Describing the date, she recounted, 'He kindly offered to pay for the meal, which I appreciated, so I suggested we head to a nearby bar afterward so I could return the favour and buy the drinks.'
However, when they arrived at the bar, the man mentioned that he had leftover drink credits from previous visits, so he did not order anything new. As a result, she ended up paying for her own drinks alone. She also noted that the chemistry in person did not quite match the spark they had during their online conversations, making the overall experience somewhat underwhelming.
'The vibe just wasn't the same as it was over chat, so after the date, our texting kinda fizzled and slowed down. I didn't reply for a few days.'
However, several days later, she was caught off guard when the man suddenly messaged her, asking her to transfer her share of the dinner bill via PayNow. See also Man asks how to recover S$60K his friend borrowed 3 years ago
'He messaged me saying the dinner was XXX each and asked me to PayNow the amount. For context, it wasn't an expensive restaurant, and let's just say he earns quite a bit and owns a condo he bought himself,' she said.
'While I do think it's a nice and gentlemanly gesture when a guy covers the bill on the first date, I'm not trying to be entitled — I'm totally fine with splitting bills and going Dutch. I did transfer him [the money], but this is the first time someone has asked me to transfer money after a first date, especially when (I assume) it's pretty clear to him that there's no second date, haha. I find it more amusing and bewildering than anything.'
Curious if others had similar experiences, she asked the forum, 'Is this normal? Would love to hear your thoughts and POV from both female and male!' 'He sees it's not going anywhere, and so he thinks he wasted his money…'
In the comments section, some Reddit users defended the man's actions, suggesting that he might have only asked for the money after feeling ignored. They speculated that while he may have initially been willing to cover the cost of dinner, the woman's lack of response after the date could have triggered his decision to request repayment. See also 6 effective approaches when dealing with difficult people at work
One said, 'He might have been ok with paying for the meal, but is now upset about the lack of a reply. I know of people of both genders who hate not getting replies, so now he asks to chop up the bill. This is not what I would have done, but I can see why some people might feel they are getting ghosted and respond in this manner. We also don't have his side of the story, so who knows what really happened?'
Another commented, 'I think it's only right to pay your share since it is a first date and neither of you is an item. I've always told my daughters not to let the other party pay all the expenses.'
However, not everyone agreed. Others felt that asking for repayment days after the date was a bad move.
One explained, 'It would have been perfectly normal for you guys to have split the meal at the time, or even if you agreed to split it, but just pay (the) merchant on a single card, and then you PayNow him instantly back there and then. See also GF ends relationship because BF's S$16,000 savings too little
But to pay for dinner and then wait a few days and send a bill, that's just weird. He sees it's not going anywhere, and so he thinks he wasted his money. Well, tough luck, this ship has sailed already.'
In other news, a woman took to an online forum to share her frustration about her boyfriend, claiming that in their nine-month relationship, he had never once initiated a date or treated her to even a simple meal.
'In these nine months, he's never initiated bringing me out on a date once, never treated me to a meal, and never surprised me with any gifts (no matter how small).'
According to her, the only times he's ever bought her anything were under certain conditions: when she asked for it, when he felt pressured to return a gift, or when he sensed she was upset and offered her a fast food meal.
Read more: 'Is this SG men these days?' — Woman says her BF never once initiated a date or treated her
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