HomeBusinessAdvice | Forget the Cheesecake Factory. Here are real first-date red flags.

Advice | Forget the Cheesecake Factory. Here are real first-date red flags.


This month, I will celebrate 32 years of marriage.

But before I got married, I had some telling dates that helped crystallize what I wanted in a mate. I learned to watch for relevant red flags.

Of the traits that were important to me in a future spouse, none had anything to do with the kind of car he drove, the clothes he wore or where he took me out.

Which brings us to a now-viral Facebook post, involving a trucker and a list of 30 places women allegedly don’t want to go on a first date.

And yes, you know already, outrage ensued.

Is the Cheesecake Factory a first date spot? It contains multitudes.

Cheesecake Factory took the top spot on the now-famous list, and fans pounced.

“Ain’t nothing wrong with the Cheesecake Factory,” Stephen A. Smith, co-host of “First Take” on ESPN, ranted on his YouTube show.

The dubious distinction also went to Applebee’s, Chili’s, Chipotle and Olive Garden. Some restaurants that skirted scorn rejoiced.

“We’re in the clear,” Shake Shack wrote in an Instagram comment.

The list was a hot topic on the “Breakfast Club” syndicated radio show and came up for debate on “The View.”

It’s all so silly. My best friend’s husband took her to Wendy’s on their first date. They’ve been married 33 years.

But all this talk about first-date restaurants has provided an opening for a conversation on what really matters.

When dating, you should be looking for relationship red flags that might make you financially incompatible. Here’s mine:

1. Having debt is no big deal

I was on a first date in my early 20s when I thought I had found my person.

The evening was going so well. The conversation turned to how excited he was about paying off his car loan.

My heart was full, because I thought he loathed debt as much as I did. I had found my frugal soul mate.

Q&A: Michelle Singletary on love and money and debt consolidation

He was fine and would be debt-free soon. Yes, mama.

But by the time we were served dessert, my date started talking about how he planned to immediately trade in his car for a BMW. When I questioned his decision to get right back into another loan, one that would be a big hit on his budget, he dismissed my concerns.

He wanted that car no matter the consequences.

Life is too short to worry about money, he said.

He did not get a second date.

When back-to-back auto loans don’t allow for adequate savings, that’s a problem.

When dates bragged about the stuff they purchased or where they vacationed and I suspected or knew their income didn’t support their lifestyle, I was out. And quick.

Opinion: The conventional wisdom about managing money and marriage is wrong

Conspicuous consumption is not cute or sexy when it’s unaffordable.

You have to know what you can tolerate. If you hate debt, don’t get involved with someone who is credit card rich.

I didn’t want to be constantly fighting with someone unwilling to pull back his spending, to the detriment of our financial future.

“What’s your sign?” was an oft-used first-date icebreaker way back when.

Should today’s version be: What’s your credit score?

You shouldn’t share intimate details of your finances, such as your income, on an initial date, but stay tuned to later discussions that indicate a pattern of bad decision-making.

If you start to get serious, it’s smart to share your credit report and credit score as a way to discuss your money personality and history. And don’t just focus on the credit score.

Credit score facts vs. myths: 5 things to know

A high credit score (FICO ranges from a low of 300 to a high of 850) simply means someone is good at managing debt. It’s not an indication they are a good person. A low score doesn’t necessary signal a pattern of poor money management. Perhaps the person has a thin credit file, or had a tough time — a job loss or illness — but is working to improve their financial situation.

But it’s important to find out if you’re about to get into a relationship with an unapologetic debtor, bent on living beyond their means.

My grandmother, Big Mama, used to say, “You can be right and wrong.”

Watch how someone tips. Are they overly pleased when leaving far less than the recommended amount, even with superior service, arguing that companies should pay their workers?

It’s not that they are wrong about the practice of tipping. Restaurant workers shouldn’t have to rely on the generosity of diners, a custom that can be sexually exploitative, since women dominate serving positions.

But until tipping is eradicated in favor of a high-enough living wage, it’s part of the price of dining out.

If your date grouses all the time about the gratuity, it should make you pause. Miserly behavior is not a good look.

If you want more personal finance advice that’s timeless, order your copy of Michelle Singletary’s Money Milestones.

5. Doesn’t like talking about money

When dating, spend time getting to know the person’s financial backstory. How did they develop certain views about money?

Do they become uncomfortable when the topic of money comes up?

I loved that my husband felt confident enough to say early in our relationship that he couldn’t afford to go on expensive dates.

We talked candidly about how we each would contribute to our outings. His frugality was endearing.

Four rules to make talking about money with your honey easier

People bring a lot of baggage into a relationship. Unpack stuff before you become deeply involved. A spender and a saver can live harmoniously, but it takes a lot of effort and communication.

Dating is an opportunity to be discerning. Look for someone who shares your values. Don’t focus on meaningless things like where you have your first date.

B.O.M. — The best of Michelle Singletary on personal finance

If you have a personal finance question for Washington Post columnist Michelle Singletary, please call 1-855-ASK-POST (1-855-275-7678).

My mortgage payoff story: My husband and I paid off the house in the spring of 2023 thanks to making extra payments and taking advantage of a mortgage recast. Even though it lowered my perfect 850 credit score and my column about it sparked some serious debate with readers, it was one of the best financial decisions I’ve made.

Credit card debt: If you’re in the habit of carrying credit card debt, stop. It’s just a myth that it will boost your credit score. For those looking to get out of credit card debt, see if a balance transfer is right for you.

Money moves for life: For a more sweeping overview of my timeless money advice, see Michelle Singletary’s Money Milestones. The interactive package offers guidance for every life stage, whether you’re just starting out in your career or planning for retirement.

Test yourself: Do you know where you stand financially? Take our quiz and read more personal finance advice.





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