Kevin O'Leary, better known as "Mr. Wonderful," thinks the biggest mistake couples make is pretending money doesn't matter until after the wedding. According to O'Leary, most partners dodge financial conversations for two reasons: they're embarrassed about having no assets, or they're hiding a messy financial past.

"Partners think that by discussing money, it may signal the wrong thing. It may be that they don't have any and they don't want to disclose that, or it may be that they have a bad financial past," O'Leary explained on X.

Why Hiding Financial Secrets Backfires

Here's O'Leary's counterargument: those hidden problems are precisely what you need to surface before marriage. "That's exactly what you wanna know. I mean, you have to deal with this problem," he said.

The investor champions prenuptial agreements not as romance killers, but as relationship builders. He believes every couple should go through the prenup process because it forces transparency and creates a stronger foundation.

Financial advisors Heather and Douglas Boneparth back this up, noting that money conversations strengthen relationships because finances intertwine with core emotions—love, security, independence, and trust.

O'Leary's take boils down to this: confronting financial realities early, including full asset disclosure and financial history transparency, isn't pessimistic planning. It's how you build something that lasts.