10 Awkward Money Scenarios to Avoid on a First Date


That first date can be stressful enough — imagine if an awkward money situation arises on top of all the other things you're worried could go wrong. Even a great date can go downhill quickly if someone makes a financial faux pas.

The key is to be prepared for any scenario so you can respond appropriately. Here are 10 awkward money moments that can happen — and dating advice on how to handle them with grace and ease.

Click through to see how to handle awkward money situations without breaking a sweat.


Your Date Forgets His Wallet

Imagine going on a first date with someone who says he forgot his wallet when the check comes. Talk about embarrassing — for both of you. This actually happened to "The Recovering Spender" author Lauren Greutman, who blogs about frugal living at LaurenGreutman.com.

She and her date were in their 20s and in college. "After we were done eating, he went to pull out his debit card to pay and realized he had left his wallet at home," Greutman said. "I thankfully had my wallet with me, so I paid." She didn't think much of that awkward first date and gave him another chance. Now they're married with four kids.

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How to Handle a Forgotten Wallet

"My advice for someone if this happens to them: Don't let it deter you from going on a second date," Greutman said. "Chalk it up to a mistake and give them a second chance. If it's something that continuously happens, then I would think about the relationship going forward."


Your Date’s Credit Card Is Declined

It's one thing to forget to bring a wallet on a date. It's another thing altogether to lack the financial means to pay. Dr. Jennifer Thomas, a financial coach for physicians, had this happen to her on a first date while in college.

He picked her up from her dorm and took her to a restaurant. "Dinner was fine, but when the check came, his credit card was declined," she said. "That was my warning sign. He was not organized financially, and I ended up paying the bill for both of us." Then she called a cab and rode home by herself.

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How to Handle a Declined Credit Card

One of the most important first date tips is to never leave home without cash or a card. "As a woman, I have learned to always have money available so I can remove myself from an unpleasant situation," Thomas said. "Proper planning and an emergency fund has saved me on more than one occasion."


Your Date Assumes You’re Going to Pick Up the Tab

For your first date, you want to keep it casual. So you suggest meeting somewhere for a bite rather than saying, "Can I take you out to dinner?" You show up expecting to pay just your share, but the other person assumes you're buying because you did the asking.


How to Handle the Tab

"After you pay you can always say, 'Okay, I'll pick up the tab, and you can get the next one,'" said longtime financial journalist Donna Freedman, author of the "Your Playbook For Tough Times" series. "If the other person makes a face or otherwise indicates that she expects the guy will always pay, then you have the option of never asking her out again."

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Your Date Orders the Most Expensive Menu Items

You want to impress your date by volunteering to pay for dinner. But then your date takes advantage of your generosity by ordering filet mignon and the most expensive bottle of wine on the menu. Now you're wishing you had suggested splitting the tab.


How to Handle a Date’s Expensive Taste

"If you're just starting the relationship, you'll need to pay for the meal," Thomas said. In the future, find more affordable restaurants or outings. If the person you're dating has champagne tastes and you have a beer budget, "you will need to compromise or have a truthful conversation about your budget," Thomas advises.


Your Date Brags About Making a Lot of Money

At the top of the list of first date questions you don't want to be asked is, "How much money do you make?" What can make the conversation even more awkward is if your date proceeds to brag about how much she earns. Her financial success sounds impressive, but you're starting to feel uncomfortable with her bragging. And you're wondering if she's going to look down on you for making less.


How to Handle a Braggy Date

You can acknowledge your date's success and change the subject, but the discrepancy in income might create problems going forward. "Be careful if you want to continue that relationship, as you will be expected to maintain his or her standard of living," Thomas said.


Your Date Wants to Share His Financial Missteps

Imagine enjoying drinks with your date and he starts telling you he's falling behind on student loan payments or that he racked up a lot of debt starting a business. Personal finance expert and millennial money coach Amanda Abella said she's been on plenty of dates with guys who've shared everything from what they owe on credit cards to debts they have in collections.

"I don't know if it's because they feel comfortable because of what I do for a living, but they aren't shy about it," she said. "However, I do see how getting this kind of information early can throw someone off on a date."


How to Handle Oversharing

Try not to judge your date too harshly if he has made some financial missteps or isn't as good managing money as you are, Abella advises. "If they want to talk about money early on, it's because they feel comfortable enough to do so, and I would take that as a good sign. It also lets you know upfront what you're dealing with. It would be far worse and painful if they weren't transparent, and then you find stuff out later," she says.

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Your Date Is Embarrassed by Your Car

If a date shows up in a clunker, you might be worried about whether it's a sign that he doesn't have his financial act together. But imagine if the tables were turned and someone refused to go out with you because he was embarrassed by your car.

This happened to a friend of Marguerita Cheng, a certified financial planner and CEO of Blue Ocean Global Wealth. Her friend is a single dad and has two cars — a minivan for driving the kids and a Porsche. Cheng said that he had been driving the minivan and didn't have time to swap it out for his Porsche, so he went to pick up a date in the family car. "His date didn't want to go out again with him because of his car," Cheng said. "She didn't think he was financially stable."


How to Handle an Embarrassed Date

As awkward as it was, Cheng said her friend should view it as a blessing that he learned about the woman's materialistic side before a relationship developed. If your date only cares about what you drive, wear or earn, she might not be the right person for you.

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Your Big Spending Is Sending the Wrong Signal

"Suppose you're flush enough to suggest a carriage ride around Central Park followed by dinner at Le Restaurant de Swank," Freedman said. "It might make you feel good to treat your date to something nice." But your date might be wondering how to compete when it's his turn to pay for a date. Or worse, your date might be wondering what you expect in return at the end of the evening, Freedman said.


How to Handle Big Spending

"No doubt some people would feel special and cherished and princessy (or princey) if someone wined and dined them spectacularly on the first date," Freedman said. "But some of us would prefer to take it slow, especially if we can't — or don't want to — compete with that kind of showboating, however well-intentioned and no-strings it might be." So save the big spending for later in the relationship, perhaps an anniversary.

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Your Date Wants to Dine and Dash

Talk about a red flag. If your date tries to leave a restaurant without paying the tab, it's a sign of some serious financial or ethical issues. If he couldn't afford the restaurant where you ate, he should've suggested someplace cheaper. If he simply didn't want to pay, the problem is a lot bigger.


How to Handle a Date Who’d Rather Dine and Dash

Your best bet is to suggest splitting the bill. If money is the issue, he might welcome your offer. But take this first date advice: Recognize that this a person you probably don't want to be involved with if he doesn't want to be financially responsible. If he still insists on dining and dashing, let him leave and pay for the meal yourself.


Your Date Asks to Borrow Money

Talk about a bold move on a first date. If your date asks to borrow money — not just to cover the tab, but a much larger amount — you might not know how to respond. You might feel compelled to help if your date tells you it's to help pay for an emergency expense.


How to Handle a Date’s Request for a Loan

Despite your date's unfortunate position, lending money to friends is a bad idea. You don't want to start a relationship with one of you owing the other. And it can become awkward if the loan isn't repaid. Let your date know that you'd like to help but don't have any cash to spare. Then suggest checking websites such as LendingTree or Prosper for a personal loan.

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