So far, so good. Then we met for dinner, and it all went pear-shaped. He did probably dominate the conversation more than he had on the phone, but I put that down to nerves. When the bill came, he told me he had forgotten his wallet. The restaurant didn’t offer Apple Pay
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I did not think of Venmo
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and didn’t want to be a pill about it, so I offered to pick up the $130 tab.

He took the receipt and said he could use it for his taxes. I have some questions. What kind of a person (a) doesn’t pay for dinner because he “forgot” his wallet and (b) proceeds to take the receipt to write it off as a business expense? Do I give this guy the benefit of the doubt and meet him again? Is this a big red flag? Is this nuts or am I crazy?

Perennially Single

Also see: ‘This guy grifted me hard’: My date chose an exclusive L.A. restaurant. After dinner, he accepted my credit card — and we split a $600 bill. Shouldn’t he have paid?

Dear Single,

You’re not crazy, it is nuts, and you deserve better.

It’s hard to forget your wallet in 2023. You got gaslighted into accepting something bizarre as something normal. Maybe in 1993 you could describe it as “normal.” Leaving home without any form of payment is almost as difficult as walking out the door in your socks — with no shoes. Your phone is your wallet. Even without that, most people would offer to Venmo or Zelle you their half of the check. Forgetting your wallet just isn’t an excuse that passes muster in the age of the smartphone.

It’s hard to believe that your date did this by accident — given that he wrote this off as a business expense. That’s two red flags. Are you supposed to be so grateful that this great guy turned up for a date that you will both pay for him and help him increase his refund from the IRS? He strikes me as the type of guy whose Tinder
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photo shows him giving an important speech to a “packed” auditorium. (The snazzy ear mic appears to have replaced the giant fish in online dating photos).

Have no doubt: People treat first dates, or first phone calls, like they would a job interview. They present the best version of themselves. They want something from you — love, romance, intimacy, financial security (in some cases) and companionship (in most cases). So you’re really only getting one side of that person. So-called love bombers, for instance, will figure out what you want and need and give it to you, but then they can turn on a dime if they don’t get the affection they expect in return. 

You can’t get the real measure of someone over just a couple of dates. You have to see them under pressure — in a restaurant with terrible service, operating a computer with a slow connection or juggling work and personal commitments — to see how they handle themselves. Is canceling plans their superpower? Is tardiness their way of showing you who’s boss? Are they cheap? You need to stress-test dates the way banks stress-test their ability to withstand financial shocks.

Ken Page, a psychotherapist and host of the Deeper Dating Podcast, says, “The skills of online dating are still the skills of dating, and the skills of dating are nothing short of the skills of intimacy. Real listening, having an appropriate level of sharing your vulnerabilities, paying attention to the person and showing interest in what they say, and simply being interested in what the person is talking about builds interest more than just complimenting them.”

People will go out of their way to impress their partner on a date, at least at first. Behold this curious statistic: 41% of people age 18 to 44 are willing to take on credit-card debt up to $2,500 in order to impress a new love interest, and just over a quarter are willing to put up more than $2,500. Put another way, two-thirds of people are willing to act like somebody who has a lot more money than they actually have. If life is a stage, online dating is a series of bad auditions.

On first dates, people start fresh without any baggage and see themselves through their date’s eyes. That could be one of the reasons for the success of the $3 billion online-dating industry in the U.S. People are searching for love, but they are also living out a series of fantasies about who they themselves would like to be — before reality kicks in. The good news for you is that you got that dose of reality on your first date with this guy. And it only cost you $130, excluding tip.

You watched him take the receipt, and put it in his pocket. That’s OK. Your No. 1 priority is to get in and out of the restaurant and date, and make it to your car, bus, or train safely. First dates can be fun. First dates can be the beginning of a beautiful friendship or relationship. And they can be perilous. So you made the right decision. Still, he did have the brass neck to write off your dinner date, which he did not even pay for, as a business expense. Write off him as a bad debt.

You can email The Moneyist with any financial and ethical questions related to coronavirus at [email protected], and follow Quentin Fottrell on Twitter.

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More from Quentin Fottrell:

I had a date with a great guy. I didn’t drink, but his wine added $36 to our bill. We split the check evenly. Should I have spoken up?

‘I spend $600 a month taking women out for dinner and drinks’: Does the man always have to pick up the check on a first date?