Cheapskate shocks woman with $250 bill for ‘dating expenses' — broken down on an Excel spreadsheet

Yahoo

10-07-2025

Falling in love can come at a high cost, nowadays — especially if you're dating a penny-pincher with access to Microsoft Office.
Nickeling and diming, wining and dining. While the acts seem to be mutually exclusive, a frugal fella proved he can be both a cheapo and a wannabe Prince Charming, creating a comprehensive Excel spreadsheet and demanding his inamorata repay him nearly $300 for their romantic outings.
And now, she's wondering if his money moves are a 'huge red flag.'
'He's been pursuing me, then sent me a spreadsheet asking to be reimbursed for our dates?? Am I overreacting?,' a 23-year-old woman asked Reddit of her 32-year-old miserly man.
Splitting the check on dates has become a hot-button issue online in recent months. While some ladies remain adamant that it's the dude's duty to cover all costs, a select few sirens don't mind going Dutch (kinda).
But this Redditor is hopelessly on the fence about pursuing a romance with a skinflint.
The troubled twosome, from Florida, has been an item for 'a little over a month now,' spending quality time together 'at least [four] times a week,' the Gen Z gal explained.
'He was very persistent in pursuing me,' she added, 'constantly texting, making plans, asking me to go on runs, bike rides, beach days, and inviting me to dinner, bars and even paying for Ubers to and from his place.'
Much to her chagrin, however, the sweet treats were no cheap thrills — and she learned that the hard way, when he stuck her with the bill.
'Hate to ask but can [you] Venmo or Zelle me some [money] for the last few weeks?' read the guy's payback ask, per a screenshot of the text message, accompanied by a snapshot of his spreadsheet.
The detailed document included dates and purchases, such as cigarettes procured on June 28, a $50 bar tab, and an $89 restaurant fee. The tight-fisted Romeo offered his would-be Juliette a to-the-penny breakdown of exactly how much dough he shelled out on each occasion.
For her share of the fun, the unsuspecting sweetheart's grand total came to a staggering $249.31.
'I know [you] got me some stuff which I'm appreciative of, and definitely happy to cover most things like our date night and drinks and stuff,' continued the Scrooge via text. 'But [you] never paid me for the first round of stuff from a few weeks ago, and money [is] a little tight for me and a source of stress [right now with] working two jobs, etc.'
Cutting her a bit of a break, the money-grubber agreed to let his paramour pay only $100 of the $249. But, after she sent the funds, he requested an additional $90 for a small debt she owed his buddy.
And, unsurprisingly, the shakedown left the Gen Zer feeling let down.
'I truly can't believe it,' she whined on Reddit, claiming that prior to pressuring her for a repayment, her love interest was a chivalrous dreamboat — he'd even waited patiently for their first kiss.
But the itemized charges felt like a kiss-off.
'It felt transactional and weirdly formal, especially since he was the one initiating nearly all the plans,' said the disillusioned darling.
'What's even more confusing,' she added, 'after sending this, he still insists on seeing me and continuing to date. Like, you want to invoice me and kiss me?'
'I've picked up the tab quite a few times [on] dinner, drinks, etc., without making a thing of it,' she ranted. 'I've never asked him to pay me back or keep score. I thought we were just getting to know each other and splitting things organically, like adults, especially since he's about 10 years older than I am.'
'So,' she questioned in conclusion, 'am I overreacting or under-reacting…[is this] a huge red flag?.'
And social media is shaking its head, 'Yes.'
'Sending you a spreadsheet is giving American Psycho,' warned a commenter. 'RUN.'
'Relationships shouldn't feel like a business transaction with spreadsheets and invoices. Fairness and trust go a long way without all the drama,' another agreed.
'This guy is a giant cluster of red flags waving around,' an equally stunned spectator wrote. 'A 32-year-old man who cannot keep his own expenses and budget in check, especially working two jobs, has other major issues going on.'