‘Was this the worst date ever?’ It was so awful that I asked her to repay me for the taxi fare. Was that wrong?

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I know you write about finance, but I recall you answering letters about dating and tipping, too, so I have a question for you.

I had dinner with a woman, paid the bill, and took her to a movie, and she didn’t even stick around for a glass of wine afterwards. If she had, I would have probably ended up paying for that, too. I also paid for the taxi from the restaurant to the cinema. She kept telling me she’d give me money for the fare, which was $24, but conveniently kept forgetting. 

As she was leaving, she made some ugly remarks about me being on my phone a lot. I had checked my phone before our food arrived because I was pinged about an item of furniture I was desperate to sell on eBay EBAY. I explained this to her at the time. I didn’t want to risk losing the bid, as more than $1,000 was at stake. 

Before she tried to walk away with the moral high ground based on alleged phone use, I asked her for her share of the taxi fare.

Before she tried to walk away with the moral high ground based on alleged phone use, I asked her for her share of the taxi fare. She gave me $10 and asked for $5 back. I told her the fare had been twice that, which it was, and put the $10 in my pocket. Frankly, I found her very critical of other people — her stories were all about how other people did her wrong. 

I prefer happy, upbeat people. I feel like I had a hangover the next day, and I honestly don’t know why I kept picking up the tab. Was I just as bad for insisting that she pay the measly $10 for the taxi? I was just so tired of her allowing me to pay for everything that I wanted to make sure she kept her word. Taxis are expensive in New York City. 

Is this the worst date you’ve ever heard of? 

Hungover

Related: ‘We have no prenuptial agreement’: Will my wife be entitled to premarital funds if I transfer them into my retirement account?

Dear Hungover,

Your date sounds like a lot.

You’re out money, you spent an entire evening with someone whose company you did not enjoy and, after you attempted to turn your frown upside down, she let you have it right between the eyes before she made her escape. To answer your questions: No, it’s not the worst date I’ve ever read about. And yes, I agree with your decision to ask for half of the taxi fare. It was a small victory, but one that probably left a bittersweet aftertaste. Still, maybe more sweet than bitter.

If she thought you were rude to text in the restaurant, she could have exited this date after dinner and before the movie. And while it’s better to leave your phone in your pocket before or during dinner, you did explain that $1,000 was at stake and that you wanted to offload the furniture. What’s more, if your personalities clashed, her negativity and your distraction were both going to be exacerbated, with each seen as a black mark against each other. 

You both tried to adhere to the social contract, perhaps against your better judgement.

You both tried to adhere to the social contract, perhaps against your better judgement. That led you to pick up the check, as you would have if you were on a date with someone you liked. Perhaps you kept hoping things would improve. But some people are just not for us, and it’s better to cut your losses early. There’s one thing that’s more valuable than money in this world, and that’s time. You both allowed a precious evening to be frittered away.

So while you should both take responsibility for your part in allowing this date to continue, if she agreed to pay half the taxi fare, which seems fair and polite after you picked up the tab for dinner, she should have stuck to her word. It would have really eaten you up if you had allowed her to leave without doing so. It also gave you the opportunity to express your displeasure with her (“I don’t like you either”). Ultimately, being able to assert yourself was worth every dollar of that $10.

Related: ‘My retirement is going to be a disaster’: I’m 59 and have $45,000 in my 401(k). I earn $72,000. Am I doomed?

You can email The Moneyist with any financial and ethical questions at qfottrell@marketwatch.com, and follow Quentin Fottrell on X, the platform formerly known as Twitter. 

The Moneyist regrets he cannot reply to questions individually.

More columns from Quentin Fottrell:

‘I paid for everything from day one’: My husband barely worked during our marriage. Can I leave my $500,000 IRA to my son?

‘We are shocked and upset’: My mother died and her second husband said he now owns everything. Is this true?

‘I trust that my husband isn’t a gold digger’: I’m inheriting millions of dollars. My husband says I’m ‘selfish’ to keep it. Should I share it?

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