Jun 15, 2026
Kevin O’Leary, who’s made a career of saying what other people are too polite to admit, has set his sights on a new target: the romantic grand gesture.
In a recent social media post, the Shark Tank investor and founder of O’Leary Ventures took aim at a common relationship ritual — the big surprise gift — declaring it a financial and emotional trap.
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Whether it’s a diamond necklace, a watch, a car or a boat; in O’Leary’s view, coming home unannounced with any of these grand items is akin to gambling with terrible odds.
“The worst thing you can do is spend a whole bunch of money and come out of there, open up the box and say, ‘Look at this, honey. I bought this for you,’” O’Leary said. “And they go, ‘I hate it.’”
His advice: skip the surprise element entirely. For major purchases, he argues, couples are better served making the decision together, which could turn the process into something meaningful rather than leaving one partner to guess what the other wants.
“I know people want the element of surprise,” he said. “It’s a huge mistake because the surprise to the downside really sucks.”
The data backs him up
O’Leary’s instinct aligns with a growing body of research on how couples fight about money, and why unilateral spending decisions are among the most corrosive.
A study published in the Journal of Social and Personal Relationships, which analyzed both Reddit posts and survey data from married couples, found that one-sided decisions — including making significant purchases made without consulting a partner — ranked among the most damaging financial conflict themes in relationships.
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Crucially, researchers also found that couples were fighting specifically about partners spending too much on gifts. “Their partners likely had good intentions,” study author Johanna Peetz of Carleton University noted, “but it still contributed to unhappiness.”
That pattern shows up broadly, too. A BMO survey of 2,500 Americans found that a third of couples find spending to be a typical argument point in their relationship, with money being the single biggest source of tension for 47% of adults aged 18 to 24.
A 2025 survey of 2,000 Americans found the average couple has 58 money-related arguments per year — with 32% of Americans saying they’re uncomfortable discussing finances with their partner at all.
Meanwhile, WalletHub’s Money & Relationships Survey found that 73% of Americans believe financial disagreements are more damaging to a relationship than political ones, and that more than one in four Americans have a financial account their partner doesn’t know about.
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O’Leary’s broader philosophy on couples and money
The gift warning fits within O’Leary’s longstanding view that financial transparency, not romantic spontaneity, is what keeps relationships stable.
He has previously told Moneywise that combining finances in marriage is “the stupidest idea” he’s ever heard, advocating instead for partners to maintain separate accounts and individual financial autonomy.
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Earlier this year, he identified uncontrolled spending as the single biggest financial threat to a marriage — worse, he said, than job loss, bad investments or market downturns. He also told Fortune that extravagant weddings are another version of the same problem — money spent on spectacle rather than on a shared financial future.
His consistent message: the most romantic thing couples can do is talk openly about money before, during and after every major financial decision. In other words, the surprise gift is a financial risk and a communication failure dressed up as a grand gesture.
What to do instead
O’Leary’s alternative isn’t to skip the gift, but to shop together.
By making a major purchase a shared experience, both partners get what they actually want, the money is spent on something with confirmed value to the recipient and no one is left feeling bad or awkward about returning a $5,000 watch.
Western & Southern’s survey found that irresponsible spending was the top dealbreaker for 41% of respondents when evaluating a partner — underscoring that how you spend money says something about who you are.
A splurge that delights could be a great gift. However, one that lands wrong, or that your partner never wanted, could be nothing more than a bill that you’re both now stuck with.
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With a writing and editing career spanning over 15 years, Emma creates and refines content across a broad spectrum of industries, including personal finance, lifestyle, travel, health & wellness, real estate, beauty & fitness and B2B/SaaS/tech.
