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The Moneyist: ‘He is financially secure and owns two homes’: I finally met the man of my dreams, but he treated our waitress like dirt and tipped her 10%. Am I overreacting?

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Dear Quentin,

I’ll keep this short, as I don’t take any pleasure in reliving it. I have corresponded with a man for two months on a dating site that shall remain nameless (except to say it starts with T and ends in R). He had a very strong and decisive personality, which I liked, and he was punctual and flew to Austin, Texas for the weekend to meet me. (He lives in Tucson, Ariz.) 

He is financially secure, and owns two homes, and is divorced with one adult child. He was the man of my dreams, or so I thought. I too am divorced (with no children). We’re both in our late 50s. He was charming to me, and asked questions, and remembered things I had told him when we FaceTimed during our early acquaintanceship. 

“‘Do some people just expect perfect service?’”

Everything was good on paper, but there were two problems: 1. He treated the waitress as if she was a nobody. He never looked at her once, smiled, made eye contact, and spoke to her like a character would treat a servant in Downton Abbey. In fact, he treated her worse than they treat their servants in Downton Abbey. 2. We went Dutch. 3. He tipped 10% for our $170 meal.

It left me with a bad taste in my mouth. He has been nothing but polite to me, but I could not help overcompensating by smiling at the waitress and saying thank you every time she refilled our water glasses. Am I overreacting? Do some people just expect perfect service? Do they deserve it in a restaurant that charges that much money for a meal? 

Still Single

Dear Single,

He does not have to impress the waitress. He wants nothing from her, so take it as a revealing insight into his character and his future behavior. If he talks to a waitress as if she is a nobody, he will treat you in the same way in time. If he becomes angry and irritable at her slow service, he will behave in a similar manner if and when he finds some of your own habits annoying. 

He wants something from you. He is searching for friendship, companionship, romance, and perhaps sex, and he needs you to like him. It’s easy to be a nice guy when you’re Facetiming
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or having dinner, and enjoying a glass of wine or two. He has everything to gain from being a gentleman. He may even see himself as Prince Charming. The waitress will likely disagree with that assessment.

Online dating is transactional. People swipe right on dating sites based on socioeconomic factors as much as physical attractiveness, whether they like to admit it or not. They take notice of clothing, vacations, living rooms, jobs, educational attainment and, yes, where they live. That’s why that information is made so readily available. As you say, he was “good on paper.”

“‘He wants nothing from the waitress.’”

Of course, people say time and again in studies that they would prefer to meet someone who is financially stable and who does not have a lot of debt. Understandably, they want to find a partner who is fiscally responsible, especially if they have worked hard to build their own finances. He spent money to come see you, you split the bill, and he tipped 10%. 

People are more reluctant to tip 20% due to inflation, nervousness about a looming recession and an end to the pandemic-era overtipping of service. People also have tipping fatigue, and they are tired of being guilted into digital tipping everywhere they go. That said, if he can afford to eat out in a fancy restaurant, he can afford to tip a waitress 20%.

Silicon Valley has commodified our personal lives: We pay for services on sites like Tinder, OKCupid, Bumble and Match.com
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and scroll profiles as if we are looking for shoes or real estate. The fact that you could both afford to eat at that restaurant suggests that you have a similar socioeconomic status. But as you discovered, that’s a low bar for compatibility. 

Check out the Moneyist private Facebook group, where we look for answers to life’s thorniest money issues. Readers write in to me with all sorts of dilemmas. Post your questions, tell me what you want to know more about, or weigh in on the latest Moneyist columns.

The Moneyist regrets he cannot reply to questions individually.

By emailing your questions, you agree to having them published anonymously on MarketWatch. By submitting your story to Dow Jones & Co., the publisher of MarketWatch, you understand and agree that we may use your story, or versions of it, in all media and platforms, including via third parties.

Also read:

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‘Am I the world’s biggest fool?’ I married my husband after being together for 25 years. Now he wants a divorce. I’ll be left with nothing. What can I do?

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