Author: Victoria Vesovski

Meeting a partner was often reliant on chance encounters — a glance across a room, a friend’s casual introduction or meeting an unexpectedly charming neighbor in the lobby of your building. Now, dating has become less about serendipity and more about strategy, subscriptions and some serious spending.

The dating services industry in Canada was valued at CA$158.9 in 2023 according to the Dating Services in Canada Market Report. What was once a swipe-based time-killer is now a full-on investment — both emotionally and financially.

The TikTok account Everybodyhasasecret recently shared the story of how one woman spent US$24,000 on a matchmaking service that paired her with the man who is now her husband. “It was worth every penny,” she said. “I know the way I met him is not your typical romantic dating story. It was very arranged and intentional.”

With US$24,000, this user paid for just five curated matches. Meanwhile, apps like Raya — the members-only dating platform that costs up to CA$62.99 a month — are seeing more people pay for exclusivity, access and maybe a second date that doesn’t involve ghosting.

As more singles start treating love like an investment, the question is no longer if people are willing to pay for connection, but whether it’s actually paying off.

The business of matchmaking

According to Maclean’s, nearly three and a half million Canadians use dating apps.

And while you might imagine online dating as something purely used by Gen Z and millennials, Statistics Canada found that 2.3% of seniors used dating websites or apps in 2022.

Apps cater to just about every age bracket and romantic niche out there. Match, for example, has carved out a reputation as a go-to platform for users over 50 — allowing up to 4,000 characters in a bio and 26 photo uploads, so you can really paint the full picture (or at least a flattering one).

Yet behind every swipe is a business model built on a paradox. Dating apps are designed to help users find meaningful connections, but each successful match means two fewer users and, potentially, two lost streams of recurring revenue.

As a result, most platforms operate on a “freemium” model: free to join, but with limited functionality. Premium features such as enhanced visibility or seeing who’s already liked your profile are often paywalled.

Dominique Laurencelle, a 37-year-old from Victoria, B.C., has been navigating the world of dating apps on and off for nearly 20 years. On a recent scroll through Tinder, she noticed the app teasing her with photos of three users who had already swiped right on her.

"But if you want to message them and swipe on them, you have to pay," she told CBC.

It’s becoming a common tactic: frustrate users just enough with the limitations of the free version and suddenly that “Upgrade to Premium” button starts looking like a lifeline. But shelling out for features doesn’t guarantee you’ll find love — or even a half-decent conversation.

Does it really work?

Unlike many dating platforms, Raya skips the freemium model entirely — there’s no free version or trial period, just a membership fee and the promise of exclusivity. But some users are starting to question whether that promise holds up.

Matt, 35, told Grazia Daily that his time on Raya was far from elite. “No real talent, just boring posers from far-flung reaches who thought it was cool to talk about private jets and air miles," he said. Another frustrated user, who goes by RachRachCity on X, says she is cancelling her Raya subscription for Linkedin Premium.

People are still willing to pay for apps like Raya — not just for the slim chance of matching with Ben Affleck or Shawn Mendes (both of whom have reportedly been spotted on the platform), but for the sense of status it offers.

Dating coach Hayley Quinn told Metro that Raya’s appeal lies in its exclusivity. “You’re not here just to meet anyone, but to meet someone as beautiful and as cool as you,” she explains.

Spending money on love doesn’t always guarantee better results. Sure, it worked for the woman who dropped US$24,000 on a matchmaking service, but a higher price tag doesn’t necessarily mean a higher-quality match.

Today, dating might feel more transactional than ever, but it’s not hopeless. If you’re navigating the dating world without a big budget, focus on platforms that align with your values and offer meaningful ways to connect.

If you do decide to pay, treat it like any other investment: know what you’re getting, set expectations and understand what success looks like for you — whether that’s a partner, a plus-one or just a decent first date.

And while serendipitous moments may feel rare, don’t write off the power of real-life encounters — sometimes the best connections happen when (and where) you least expect them.

Sources

1. Global Newswire: Dating Services in Canada Market Report 2024: Competitive Landscape, Key Stats, Current Performance, Industry Outlook

2. TikTok: If you could afford to pay $24,000 to meet the love of your life, would you ????

3. Maclean’s: Online Dating is Out. Real-Life Romance is In. by Treena Orchard (July 23, 2024)

4. Statistics Canada: Canadian seniors more connected than ever (August 14, 2023)

5. CBC: How dating apps frustrate you into paying for them (March 20, 2024)

6. Grazia Daily: Everything To Know About Raya – The Exclusive Dating App Used By Celebs (May 12, 2025)

7. X: @RachRachCity

8. Metro: I spent months on Raya’s waiting list, but this is why it’s worth it by Alice Giddings (March 23, 2025)

This article provides information only and should not be construed as advice. It is provided without warranty of any kind.

When a loved one is in need, lending a helping hand can feel like second nature — even with a price tag.

On a recent episode of his new Netflix talk show, Everybody’s Live With John Mulaney, the comedian explores what it really means to help someone — and the consequences that can follow.

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He’s joined by actor Michael Keaton and Jessica Roy, a personal finance columnist for the San Francisco Chronicle. Their first caller was Dylan from Montville, New Jersey, who borrowed $20,000 from his brother to attend law school. But instead of cracking open textbooks, Dylan bought a car. Then he crashed it. After selling the wreck for scrap, only $1,200 of the original $20,000 remained.

Now, Dylan finds himself in a bind: no money, no law degree, a totaled car and a $20,000 lie he has to repay.

It’s a cautionary tale and one that might hit closer to home than you’d expect. Whether you’ve loaned money to a loved one or considered asking for help yourself, navigating finances within personal relationships can be tricky.

Being a good friend

When money enters the mix between friends and family, the emotional toll can often outweigh the financial loss. A LendingTree survey found that 31% of Americans are owed money by a loved one — with friends and siblings being the most common borrowers.

The top reason? Covering debt payments and everyday expenses like meals and gas. But personal lending often comes with strings attached: nearly half of the respondents said they regretted lending money to someone close, and one in six admitted it had damaged a relationship.

In the episode, Roy emphasized that lending money to someone you care about requires a mental shift.

“Any money you loan someone you need to be psychologically detached from it,” she explained. “It’s a gift and I’m not going to get it back.”

It’s a mindset that protects more than just your wallet — it safeguards your relationships, too. When lending to friends and family, boundaries are just as valuable as budgets.

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Stuck in a tough spot

Dylan found himself in a messy situation. Not only did he lie to his brother about using the $20,000 loan for law school, but now he has no way to pay it back. He mentioned buying a van for $500, which led Roy to suggest he start a side hustle — like driving for Uber — to begin earning money.

According to LendingTree, 38% of Americans have a side hustle, whether it’s delivering food, freelancing or picking up seasonal work. For many, these gigs aren’t just for extra cash: 61% say their life would be unaffordable without one.

But earning money is only part of the solution — Dylan also needs to come clean. His brother still believes he’s in law school.

“I would talk to your brother and come up with a good faith repayment plan of however much you can commit to,” Roy advised.

Dylan should also consider building a budget to get his finances back on track. That means taking stock of any income — including side hustle earnings — and mapping out monthly expenses like gas, food and debt payments.

Even setting aside small amounts consistently — say, $50 or $100 a week — can build momentum toward repaying the loan. Beyond that, budgeting can help Dylan understand where his money is going, avoid future financial missteps and rebuild trust — not just with his brother, but with himself.

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This article provides information only and should not be construed as advice. It is provided without warranty of any kind.

Despite policy shifts under the Trump administration — from tariffs to immigration to federal spending — Federal Reserve Chair Jerome Powell says the U.S. economy remains on solid footing.

While the long-term effects of the policy changes continue to unfold, Powell signaled no urgency to adjust monetary policy, citing a strong labor market and easing inflation as signs of underlying resilience.

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Speaking at the Society for Advancing Business Editing and Writing (SABEW) conference, Powell noted that inflation has fallen significantly from its 2022 peak, even though recent progress toward the Fed’s 2% target has slowed.

“We look at inflation which is the change in prices and we’re seeing that it has come down quite a bit and unemployment is actually low, it’s very close to measures of maximum employment and the economy is growing,” he said.

New jobs data released in May showed 177,000 positions added in April. However, the unemployment rate remained unchanged at 4.2%.

While the numbers suggest stability, many Americans aren’t feeling it. With the cost of everyday essentials still climbing, consumer sentiment continues to lag behind the Fed’s optimism — a disconnect that could shape economic policy in the months ahead.

The market looks fine on paper

Recent employment may reflect a relatively stable U.S. job market, but Americans remain anything but reassured. A January survey from résumé service MyPerfectResume found that 81% of U.S. workers are worried about losing their jobs in 2025.

The Trump administration has introduced sweeping policy changes, including large-scale federal layoffs, deep budget cuts, new tariffs and strict immigration enforcement. While the full impact on the labor market has yet to be felt, these measures have already stoked anxiety across multiple industries — from government agencies to tech and manufacturing.

“The March employment data is the calm before the potential tariff-related storms,” Dana Peterson, chief economist at The Conference Board, told CNN.

Workers’ unease is understandable as they navigate a landscape filled with economic uncertainty and potential aftershocks. Even though job numbers haven’t plummeted, the fear of what lies ahead is keeping many employees on edge.

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Is inflation really cooling?

For many Americans, the sting of inflation is still being felt — especially at the grocery store.

According to the USDA’s Agricultural Marketing Service, egg prices have cracked wide open — rising 63% over the past year. Bureau of Labor Statistics data shows the national average price for a dozen eggs hit $5.90 in February, making a basic breakfast item feel more like a luxury.

Powell acknowledged the ongoing strain during his remarks at SABEW, attributing much of today’s high prices to lingering pandemic-era inflation. He emphasized that overall inflation has cooled since its 2022 peak — but that the road ahead is uncertain.

The Trump administration’s new tariffs could reignite inflation in the coming months. Powell noted that it’s still too early to gauge the full impact, as details such as which goods will be affected and whether trade partners will retaliate remain unclear.

“Our obligation is to keep longer-term inflation expectations well-anchored and to make certain that a one-time increase in the price level does not become an ongoing inflation problem,” Powell said.

Now’s a good time to revisit your budget and take stock of where your money’s going. Small changes — like cutting back on impulse buys, pausing unused subscriptions or buying bulk — can free up more funds than you’d think. Even in times of uncertainty, a mindful approach to spending can bring a sense of control.

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Like what you read? Join 200,000+ readers and get the best of Moneywise straight to your inbox every week. Subscribe for free.

This article provides information only and should not be construed as advice. It is provided without warranty of any kind.

Thomas McPeek didn’t just stumble into a lucky streak — he studied for it.

The 24-year-old from Chicago spent last year diving into the world of sports betting, placing dozens of complex, high-risk wagers on football — called parlays — based on odds he believed he could beat.

“It was a calculated attack where I thought I had an edge,” McPeek told CBS News Chicago.

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In August, he visited the sportsbook at the Horseshoe Casino in Hammond, Indiana, owned by Caesars Entertainment. To ensure his bets wouldn’t be rejected, he remained anonymous, making multiple small bets at kiosks instead of with a clerk at a counter.

He even went so far as to disguise himself with sunglasses or hiding his hair.

Over the course of a single week, McPeek says he bet around $30,000 and won $350,000.

A month later, he traveled across state lines to employ the same strategies at another Caesars property — the Isle Casino in Bettendorf, Iowa. This time, he says his tickets totaled about $450,000 in winnings.

But McPeek says when he tried to cash in, both casinos voided his tickets, citing house rules and anti-money-laundering policies. He says he’s willing to sue to get his winnings.

Where’s the money?

McPeek maintains that he played by the rules but Caesars says he tried to circumvent them, particularly by crossing state lines — something that can violate betting regulations.

Scott Morrow, a former casino executive who now teaches gaming at the University of Nevada—Las Vegas, says Caesars was justified in voiding his tickets on those grounds.

“I have a tough time finding sympathy for his case,” Morrow said.

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But Eli Feustel, a seasoned betting expert and author, sides with McPeek — not because of how the bets were made, but because of Caesars’ timing in voiding his wins. He argues that the casinos only acted after realizing McPeek might actually win.

“The clear answer is Caesars owes this,” he told CBS News.

The Indiana Gaming Commission says Caesars followed the rules. Now, regulators in Iowa are reviewing McPeek’s complaint.

Against the odds

Caesars has banned McPeek from playing at their casinos but is willing to pay back the money McPeek used to place the bets.

Blue Chip Casino in Michigan City, Indiana, also banned McPeek from playing at their casino after he won $127,000, but at least Blue Chip paid him out first.

With Americans spending more than $60.4 billion on commercial casino gaming and sports betting in 2022 — up 14% from 2021 — some wonder if the house plays fair when the odds shift in the bettor’s favor.

For gamblers navigating the high-stakes world of sports betting, McPeek’s case is a cautionary tale.

Here are three ways to ensure you can cash in on your sports bets.

1. Read the fine print before you place any bets. Sportsbooks include detailed rules in their terms and conditions — including the right to void wagers. Knowing those rules ahead of time can keep you from betting into a gray area.
2. Keep your bets to one jurisdiction to avoid raising red flags and accusations of gaming the system.
3. Document everything as you game, from screenshots to transaction receipts. Keeping a trail could make or break your case if things get contested.

Even if the odds are in your favor, the rulebook — and how it’s enforced — might not be.

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Like what you read? Join 200,000+ readers and get the best of Moneywise straight to your inbox every week. Subscribe for free.

This article provides information only and should not be construed as advice. It is provided without warranty of any kind.

The tables are turning in the U.S. housing market, and this time, buyers are calling the shots.

There are an estimated 1.9 million homes for sale across the country, but only about 1.5 million active homebuyers. That leaves a gap of nearly 500,000 — the largest on record, according to Redfin.

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“The balance of power in the U.S. housing market has shifted toward buyers, but a lot of sellers have yet to see or accept the writing on the wall,” said Redfin Senior Economist Asad Khan. “Many are still holding out hope that their home is the exception and will fetch top dollar.”

U.S. home prices were still up 3.9% year over year in February — a slight dip from January’s 4.1% gain — but a growing supply of homes and easing mortgage rates are cooling the market, according to the S&P CoreLogic Case-Shiller Home Price Index.

That’s left some sellers — especially those who bought at the peak — trying to recoup their investment just as buyer demand starts to slow. With listings rising and buyers getting more selective, the big question is: Is now the best time to sell?

A shift in control

Redfin economists expect home prices to dip by about 1% by the end of 2025. Demand is already down. Sales of existing homes fell 1.1% year over year in April, hitting a six-month low.

Buying a home remains a major financial leap. With economic uncertainty fueled by tariffs, layoffs and shifting federal policies, many would-be buyers are hitting pause on one of life’s biggest purchases.

Sellers are already feeling the sting. Take a single-family home in Sonoma, California: once listed for over $3.5 million during the pandemic boom, the 3-bedroom, 4-bathroom property eventually sold for $1.86 million — nearly half its original price.

The home saw several price cuts before it sold in April for 6.8% below its most recent $1.995 million asking price, according to Zillow, as reported by Newsweek.

That sale reflects how far the market has come from its 2021 peak. Back then, rock-bottom mortgage rates and limited inventory fueled bidding wars and drove up prices. But now, things look different.

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The balance tips further

If you’re thinking about selling, don’t wait too long. Listing sooner could help you avoid chasing a cooling market. And if your home’s already listed and not getting much attention, it may be time to switch gears — whether that means adjusting your asking price or making small, high-impact upgrades to help it stand out.

Many homeowners are still pricing based on what they paid during the market’s pandemic-era peak, not what today’s market will bear.

“A lot of the people selling right now bought in 2021 or 2022, when home prices were near their height,” said Corey Stambaugh, a Redfin Premier agent in North Carolina. “Even though we advise them to list at today’s market value, a lot of them decide to list high to recoup their money.”

But overpricing your home isn’t just wishful thinking — it can be a costly mistake. Properties that sit too long tend to raise red flags to buyers, giving them more leverage to negotiate.

For buyers, the market is starting to tilt in your favor, but that doesn’t mean you shouldn’t go in unprepared. Getting pre-approved can make you a stronger buyer and help you stay realistic about what you can actually afford. When you’re ready to make an offer, negotiate like your rent just went up. You might be able to ask for repairs, appliances or even that oddly charming mid-century credenza in the living room.

Whether you’re buying or selling, the key is knowing when to move — and not being afraid to play a little hardball when the timing’s finally on your side.

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• How much cash do you plan to keep on hand after you retire? Here are 3 of the biggest reasons you’ll need a substantial stash of savings in retirement

Like what you read? Join 200,000+ readers and get the best of Moneywise straight to your inbox every week. Subscribe for free.

This article provides information only and should not be construed as advice. It is provided without warranty of any kind.

A landlord-tenant showdown is unfolding in Borough Park, and it’s raising questions about housing rights, health needs and who gets to decide who stays and who goes.

Landlord Aneiello DeGiuda, a diabetic homeowner in a multi-family building, says climbing the stairs has become too much for him. He wants to move into the more accessible first-floor unit — but it’s already occupied by his tenant, Kenyatta Blakely.

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Blakely isn’t budging, arguing DeGiuda can’t just kick him out. If the landlord wants the apartment back, Blakely says, he needs to follow the law.

Local police confirmed that there have been harassment complaints filed, citing text messages from DeGiuda that made Blakely uncomfortable, including photos showing him entering and leaving the apartment. DeGiuda denies any wrongdoing.

“He tried to file a harassment charge because I’m asking him for the rent, which he hasn’t paid,” DeGiuda told News 12.

Now, DeGiuda says Blakely has 90 days to vacate the unit — or things could escalate further.

Eviction laws are clear, but so are building violations

DeGiuda may hold the deed, but he doesn’t hold the power. In New York, tenants are protected under strict housing laws, which means a landlord can’t simply decide when someone has to leave. Eviction is a legal process that starts with a written notice to vacate. That notice period can range from three to 30 days, depending on the state, and must be backed by a legally valid reason.

Wanting easier access to the first-floor unit for health reasons might tug at the heartstrings, but it doesn’t meet the legal standard for eviction.

Still, things got messier. DeGiuda claimed Blakely has stopped paying rent and is now past the five-day grace period. Blakely argued that no one should be paying rent at all — not in the current state of the building.

According to the Department of Buildings, the cellar unit has been under a vacate order since 2022 due to a lack of lighting, ventilation and required permits. Inspectors even found the vacate notice had been torn down and taped back up — a violation that could carry fines of up to $12,500.

This kind of standoff isn’t rare. Between 2000 and 2018, landlords in the U.S. filed an average of 3.6 million eviction cases each year, according to research published in the Proceedings of the National Academy of Sciences.

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Next stop: Housing court

In New York City, landlord-tenant disputes are often a legal chess match. And according to the law firm Blodnick Fazio & Clark, many cases drag on or end unfavorably for landlords simply because they don’t follow lease terms or the legal procedures required by law.

Blakely may be withholding rent — and for now, he might be able to get away with it. While it’s rarely a good idea to stop paying rent outright, tenants do have rights, especially when their living conditions are unsafe.

In this case, the Department of Buildings has issued a vacate order on the unit due to code violations. But that doesn’t mean tenants can automatically stop paying rent. Unless a court or housing authority says otherwise, rent is still legally owed — even if the unit is in poor condition.

That’s why it’s important to do your due diligence before signing a lease, especially in a complex market like New York City. As for a written lease, meet your landlord in person if you can and inspect the property for red flags like unfinished renovations, missing permits or poor ventilation.

Watch out for so-called “danger clauses” in your lease, such as giving the landlord the right to enter your unit at any time or cancel the lease if the building is sold. You can also search for existing violations by checking the property’s record with the city’s Department of Buildings.

And before you take matters into your own hands, consider talking to a tenant advocate or attorney. With the right guidance, you can protect your rights — and avoid getting caught up in a legal mess.

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• Here are 5 ‘must have’ items that Americans (almost) always overpay for — and very quickly regret. How many are hurting you?
• How much cash do you plan to keep on hand after you retire? Here are 3 of the biggest reasons you’ll need a substantial stash of savings in retirement

Like what you read? Join 200,000+ readers and get the best of Moneywise straight to your inbox every week. Subscribe for free.

This article provides information only and should not be construed as advice. It is provided without warranty of any kind.

Danish pharmaceutical company Novo Nordisk — best known for its blockbuster weight-loss drugs Ozempic and Wegovy — has signed a $2 billion deal to acquire the global rights to an experimental obesity treatment from China’s United Bio-Technology (Hengqin) Co.

The March 24 agreement includes milestone payments of up to $1.8 billion, plus tiered royalties.

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The new drug in question, UBT251, is a next-generation therapy designed to tackle obesity and type 2 diabetes by targeting three key hormones including, GLP-1 and GIP — which regulate appetite and blood sugar — and glucagon, which helps stabilize blood sugar levels.

Roughly 15.5 million U.S. adults have already used injectables for weight loss, according to Gallup. With access to weight-loss medications still limited by patchy insurance coverage, UBT251 may face the same barriers, even as it promises new possibilities.

Here’s what this deal means for Americans looking for alternate treatments for their diabetes or chronic obesity.

Taking over the market

In the past, Senator Bernie Sanders has criticized Novo Nordisk (NYSE:NVO) for charging American patients far more than their international peers for the same medications. However, CEO Lars Fruergaard Jorgensen has blamed the U.S. health care system’s bureaucracy and markups for the high prices.

But now, Novo Nordisk has changed its pricing model with the launch of NovoCare Pharmacy — a direct-to-patient service offering all doses of Wegovy at $499 per month for patients paying cash. This strategy was designed for those without insurance or whose plans don’t cover weight-loss drugs.

Ozempic’s insurance coverage dropped 22% from 2024 to 2025, according to GoodRx, leading to 1.1 million Americans having no access to these medications.

"If only certain patient populations get access to these medications — those primarily with private insurance, more generous health plans — then there’s a huge percentage of the U.S. population that isn’t getting access to these medications," lead author Christopher Scannell told Axios.

When Novo unveiled its latest retail gambit, Wall Street raised a glass as the stock also surged nearly 4%. However, it remains unclear — in a system rife with co-pays and corporate contracts — whether this will translate into improved access or affordability for American consumers.

Read more: Want an extra $1,300,000 when you retire? Dave Ramsey says this 7-step plan ‘works every single time’ to kill debt, get rich in America — and that ‘anyone’ can do it

Will this make a change?

Despite the excitement surrounding NovoCare, the company’s U.S. strategy has faced some ups and downs. Since last summer, Novo Nordisk’s stock has dropped by nearly 50% — reflecting investor concerns about pricing pressure, increased competition and lingering supply chain issues.

Last year, the overwhelming demand for Ozempic and Wegovy led to widespread shortages in the U.S., prompting regulators to allow compounding pharmacies to replicate the drugs — often at a lower cost. That shift disrupted the market and Novo Nordisk responded with a renewed push for its own branded products. NovoCare is part of that strategy.

"Novo Nordisk continues to advance solutions for patients that improve affordability and access to our medicines, whether they have insurance or not,” said Dave Moore, President of Novo Nordisk Inc.

But with insurance coverage for weight-loss drugs still limited and ongoing questions about affordability, it’s too early to tell whether this latest deal — and the rollout of UBT251 — will meaningfully lower costs or intensify market competition. For now, Novo Nordisk seems determined to dominate the playing field — but the question remains: will everyday Americans be able to afford to join the game?

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This article provides information only and should not be construed as advice. It is provided without warranty of any kind.

First dates already come with unspoken tests, but one new trend — the so-called “gold digger test” — is turning dinner into a financial trap, leaving some singles blindsided and offended.

Imagine this: You’re on a date set up by a mutual friend. You’re financially independent, settled in your career, own your home and you aren’t looking for someone to complete your life — just someone to add joy to it.

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The date starts strong. Conversation flows easily, you bond over your shared love of hiking and weirdly niche documentaries, and for a moment, you think: This might go somewhere. Then the $200 bill arrives, and your date slides it across the table to you. There’s no offer to split it, no wallet shuffle — just silence.

Confused but not wanting to kill the vibe, you pick up the tab. That’s when your date grins and says, “Congrats, you passed! You’re not a gold digger.”

Welcome to the latest viral (and dubious) way some singles are trying to weed out dates they think are only in it for the free meal. But is it a smart check for sincerity or just a manipulative money move?

The not-so-smart test

Maybe your date doesn’t even try to justify the test. Or perhaps they say they’ve been burned before by someone who only saw them as a walking credit card. But dragging that baggage into a new connection with a “gold digger test” isn’t exactly the healthiest way to start something new.

Conversations about money can feel vulnerable, especially if past experiences made you cautious. And yet, it’s easy to see where the fear comes from. According to recent data from Experian, nearly 1 in 3 young adults have discovered that their partner made a major financial purchase behind their back.

On an episode of Experian’s Cost of Loving podcast, James Jones, Head of Consumer Affairs at Experian, talked about how the rise in mistrust between partners raises a concerning issue.

“Whilst joint finances aren’t an essential part of a relationship, it’s worrying that many people have such a lack of financial confidence in their partner,” he said. “The only way to create change here is to encourage financial transparency.”

Of course, there’s a time and place for money talk. First dates can be a good moment for light chats about values, but dropping a financial loyalty test at the table isn’t it. If anything, it says more about someone’s unhealed wounds than your willingness to cover dinner.

Read more: Want an extra $1,300,000 when you retire? Dave Ramsey says this 7-step plan ‘works every single time’ to kill debt, get rich in America — and that ‘anyone’ can do it

A better way to have the money talk

Trying to gauge how someone handles money doesn’t have to be off the table. Money conversations are a key part of any healthy relationship.

According to a LendingTree study, 98% of Americans in exclusive relationships say financial compatibility matters, and 67% say it’s very important. Still, that doesn’t mean you need to dive into budget spreadsheets over your first round of drinks. Financial expert Ramit Sethi told Moneywise he’s not a fan of jumping into finance chat too soon.

“Some people in the financial community encourage talking about money on the first date,” he said. “I find that a little nerdy. Like, who wants to be on a first date talking about your asset allocation? You know, it’s like, get a life.”

Instead of starting with the hard numbers, look for the soft signs: how someone spends, saves and thinks about value. If one person prefers fancy dinners out and the other’s more into budget-friendly home-cooked meals, talk about how to strike a balance.

And be clear about the basics — like who’s paying. Whether you take turns, split the bill or each cover certain expenses, agreeing on expectations early can help avoid awkward moments later.

If things get serious, it’s time to get financially naked. Be open about debt, savings goals or any financial responsibilities you’re managing. Transparency builds trust. Sneaky tests? Not so much.

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• Here are 5 ‘must have’ items that Americans (almost) always overpay for — and very quickly regret. How many are hurting you?

Like what you read? Join 200,000+ readers and get the best of Moneywise straight to your inbox every week. Subscribe for free.

This article provides information only and should not be construed as advice. It is provided without warranty of any kind.

Americans have long grumbled about tipping culture — but now digital checkout screens are turning that frustration into full-blown financial disasters.

Sometimes, the issue isn’t just pressure to tip — it’s how easy it is to make a costly mistake. One in five Americans say they’ve accidentally tipped more than intended on digital checkout screens, according to an exclusive Opinium poll for DailyMail.com on tipping culture.

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That’s exactly what happened to Linda Mathiesen. While buying CBD pain relief gel at a store in San Bruno, California, she accidentally tipped $5,000 on a $129.28 purchase.

Mathiesen said she meant to leave a $5 tip, but the payment terminal didn’t show a decimal point, so when she entered “5000,” the system took it — literally.

At first, the clerk at San Bruno Exotic told her the charge couldn’t be reversed. Then the story shifted — he claimed the shop never received the money. But Mathiesen’s bank statement showed otherwise.

“I’m just livid because I’m like I’m not going to pay $5,000 for something I never intended to happen,” Mathiesen told ABC 7 News.

A tipping error gone wrong

For Mathiesen, a $5,000 tipping mistake wasn’t just a moment of panic — it became a financial crisis. As a special education teacher living on a fixed income, she didn’t have the cushion to absorb the hit. With no emergency savings to fall back on, the charge was devastating.

And she’s not alone. According to the U.S. News survey, 42% of Americans have no emergency savings, despite experts recommending three to six months’ worth of expenses.

Mathiesen contacted Wells Fargo within five minutes of the transaction, but says the bank has done little to help, despite its promise of “zero liability protection” for promptly reported fraud.

The bank’s website says its “built-in protection features ensure that you won’t be held responsible for unauthorized transactions, as long as they’re reported promptly.” Yet, a year later, Mathiesen is still fighting to get the charge reversed.

"I busted out in tears,” she told ABC 7 News. "My son is graduating college next week … and I can’t even buy anything for him because I have $5,000 outstanding … now it’s $5,500!"

Read more: Want an extra $1,300,000 when you retire? Dave Ramsey says this 7-step plan ‘works every single time’ to kill debt, get rich in America — and that ‘anyone’ can do it

It’s not as rare as you’d think

Digital checkout screens may speed things up, but one wrong tap can turn a routine purchase into a nightmare.

It happened to Vera Conner, too. The Georgia woman was ordering her usual No. 4 Italian sandwich at Subway — priced at $7.54 — when she accidentally left a $7,112.98 tip.

Conner said she was entering her phone number for loyalty points when the screen suddenly flipped to the tipping prompt. Before she realized what had happened, the charge went through.

After hours of calls with Subway and Bank of America, she eventually got the charge reversed — but not without major stress.

If you ever find yourself in a similar situation, there are steps you can take:

• Act fast. Contact your bank or card provider as soon as the transaction posts. The faster you report it, the stronger your case. Most banks allow 60 days to dispute a charge, but don’t wait that long.
• Document everything. Screenshot the receipt, the payment screen if you can and keep records of any communication with the merchant. These details help prove the error wasn’t intentional.
• Know the fine print. Many banks offer protection against unauthorized transactions, but not all mistakes qualify. If you technically authorized the payment, even by accident, you may be out of luck unless the merchant agrees to reverse it.
• Build an emergency fund. It’s not just for layoffs or medical bills. Sometimes it’s for the unexpected stuff — like tipping $5,000 for a $129 product.

What to read next

• JPMorgan sees gold soaring to $6,000/ounce — use this 1 simple IRA trick to lock in those potential shiny gains (before it’s too late)
• This is how American car dealers use the ‘4-square method’ to make big profits off you — and how you can ensure you pay a fair price for all your vehicle costs
• Here are 5 ‘must have’ items that Americans (almost) always overpay for — and very quickly regret. How many are hurting you?

Like what you read? Join 200,000+ readers and get the best of Moneywise straight to your inbox every week. Subscribe for free.

This article provides information only and should not be construed as advice. It is provided without warranty of any kind.