May-December relationships are trending, but let’s be honest—they never really went away. They come with heat and headlines. But behind the sexy story is a mix of real-world intrigue: Sex, money, and what everyone else thinks. Judgmental kids. Unsolicited advice from “friends.” Awkward stares. Clashing timelines. We talked to couples who’ve made it work—and the experts who know what it takes. Love doesn’t care about the age gap. But your bank account, your body, and your family? They might.

When Danielle met Larry in 2005 during a production of Oliver they were in, she had no clue she had found her soulmate. Two years later they had their first date and realized quickly that their relationship was going to be serious.

And it was.

We Fell in Love. Everyone Lost Their Minds.

But one thing bothered Danielle’s mother—their age difference. Danielle is 43 and Larry is 64. “My mother was less than thrilled. Once it became clear that this would be the man I was marrying, she started warming up, but the age thing is always going to bother her,” said Danielle.

They got married in 2009 and have two sons—Hugh 13, and Harry, 10—and it wasn’t only Danielle’s mother who was troubled by their age difference. “Some people had plenty to say and were nasty about it. They’re no longer in our lives. It’s satisfying to have proved them wrong. Larry is my soulmate. I only wish I met him sooner,” said Danielle.

Is Age Nothing but a Number?

May-December relationships—couples who have at least a decade of difference in their ages—are nothing new, but the topic is trending with celebs like Cher making headlines for being 40 years older than her boyfriend and films like Babygirl, and last year’s Oscar-nominated May December. While this is an era where 80 is the new 60, some still look sideways at May-December couples. Guess they didn’t get the memo that age is just a number or that yes, many times love conquers all.

“We’re very alike. It feels like we’re the same age or ageless. When it’s love, it doesn’t matter what anyone else says,” said Danielle.

When the Age Gap Becomes the Power Dynamic

May-December relationships often thrive on a dynamic Clint Kreider, LMFT (Licensed Marriage and Family Therapist) with Still Water Wellness Group, calls “mutual mentorship.” The older partner brings life-tested wisdom and stability, while the younger one injects fresh perspectives and spontaneity—a balance that can deepen emotional intimacy. “In my practice, I’ve worked with couples where a 20-year age gap became a bridge, not a barrier. One client in her 50s, dating a man in his 30s, shared how his tech-savvy curiosity rekindled her passion for travel, while her financial acumen helped him build credit,” said Kreider.

Love Is Easy. The Judgment Sucks.

But when it comes to matters of the heart, there can be hurdles, and May-December couples are no exception. Many issues can arise. Is someone having a midlife crisis, being a gold digger, or has an unhealthy daddy complex? It could be that the older man doesn’t want children. What if he retires a decade before his partner, or worse, if whoever is oldest gets gravely ill? The list goes on from there, and experts have plenty to say.

Caregiving, Retirement, and Other Sexy Topics

Stephen Golant, PhD, professor emeritus at the University of Florida and a gerontologist, said lifestyle conflicts are more likely as older men move into advanced ages and have less energy or functional abilities to enjoy the same experiences as younger spouses. He pointed out that there’s a high probability that younger women will become caregivers for older men.

“Whether this is looked on positively may depend on the willingness of the younger woman to function as chauffeur, handyperson, care worker, financial advisor, social counselor, nurse’s advocate, and emotional confidant to address their chronic health problems and mobility declines,” he said.

On top of that, he said her efforts may not be viewed favorably by adult children (e.g., the adult daughter of an older spouse), who disagrees on how she handles her father’s needs. Chances are too, he said, that a younger woman will become a widow and age alone.

Then there are the financial issues.

What About the Money?

Jim White, the founder of Great Oak Wealth Management, highlighted some examples, such as differing retirement dates. “Age-gap couples need to plan for an overall longer retirement window. Although most couples want to retire simultaneously, timing retirement could be difficult for age-gap couples,” said White.

Many struggle to find the perfect balance between working long enough to ensure suitable savings and retiring with enough time to travel, volunteer, or visit grandkids when both are healthy and active.

Health issues may also have financial impact.

The older spouse may have increasing health care expenses or even require long-term care, which can drain a couple’s savings, leaving the younger spouse with little to live on. As for health insurance, if you retire before Medicare eligibility at age 65, this can be a considerable expense. For the younger spouse, sticking with your job for a few more years increases retirement savings and, most importantly, provides health benefits.

Another concern is the Social Security claiming decision, since the younger spouse may live much longer than the older one. “If the older spouse is the higher earner, it could be beneficial for them to delay taking benefits until age 70. The benefit will grow by about eight percent for each year of delay,” said White, who recommends talking to a financial advisor about the best Social Security strategy.

Who Gets What When He Dies?

Estate planning is also critical. An age-gap marriage is often the second marriage for one or both spouses, and children from a previous marriage can complicate family dynamics. “If one spouse wants to provide for the younger spouse while also leaving something for the children, this could cause family squabbles,” said White.

Often, age-gap spouses make the new spouses the primary beneficiaries. If the children are secondary beneficiaries, they may not see any inheritance since the new spouse can change the beneficiary if they take over the account—nor are they obligated to provide anything to their stepchildren.

White said the best solution is to, “Meet with an estate planning attorney to create an estate plan that balances the longevity issues related to a younger spouse and ensures children from a previous marriage are covered.”

When it comes to finances, it’s not all negative. Situations with significant retirement savings can be advantageous for couples with a large age difference. The older spouse reaches 59-1/2 sooner and can access their retirement account without penalty, which may allow the younger spouse to retire. On the flip side, when the older spouse hasn’t saved enough for retirement, the younger one can continue to work, providing a stable income for an extended period.

Still Hot. Still Here. Still in Love.

Despite challenges, a May-December relationship can be a love supreme.

Sherrie, 71, and Don, 81 have been together 45 years and never married. They built a semi-truck body shop business together that they closed when Don retired, and Sherrie runs a nonprofit she founded. He had three kids, she had none.

She said they navigated “many rough early years, with ex-partners and parenting issues, and the ups and downs of running a business. But we compare our situation to what other directions we could be experiencing and remain thankful we have each other as best friends to lean on.”

Sherrie said their age difference was never an issue for their family and friends. Her parents liked him from the outset, and she got along well with his longtime friends.

She reflected on their years together, “I wouldn’t change a thing. My getting three additional children to love beside our child together is priceless. In the big picture, 10 years difference in age is nothing. We make each other laugh a lot. Laughter lifts the heart, ties the connection.”

Want It to Work? Read This First.

Gayle MacBride, PhD, a licensed psychologist with Veritas Psychology Partners, said it’s important for couples to talk about their respective places in life—do you want to have children, what will the older spouse do in retirement while the younger spouse works?—and recognize they may be different, but neither is necessarily wrong. “Finding ways to honor both preferences, when able, is key to navigating different life stages,” said MacBride.

You may reach a point when energy levels and abilities to be active differ, which can make older partners feel left behind or excluded. “Find shared activities but continue to have separate interests and make sure these activities are kept in balance with the things you do together,” MacBride added.

The reality is friends and family may be negatively judgmental and assume things that aren’t true of your partner. Have a united front. “You don’t have to justify your relationship but be clear with yourselves and them about your commitment,” said MacBride.

Find other “May-Decembers” for your social group. Talk about things like role expectations. Also understand that you may miss some of your partner’s cultural experiences and references. Meet these with curiosity and keep a non-judgmental stance. Enjoy the upside.

“The diversity in age provides just that, diversity to your world. Having an outlook different from your own naturally challenges your thoughts and decision-making process, often leading to better and more sound decisions,” said MacBride.

Kreider offered a final thought, “Love across decades isn’t about ignoring the gap—it’s about building a life where both partners feel equally seen, today and tomorrow.”