There used to be a time when it was considered shocking for women to cross the age gap by dating a younger man, but today May-December romances are on the rise. Despite this growing trend, romantic liaisons between older women and their “toy boys” remain the subject of gossip, dispute and sly winks. Some believe that the age difference may impede the relationship but if the couple has enough in common, can an older woman and a younger man’s relationship develop into something enduring?

There is an abundance of famous examples such as Robin Wright and Ben Foster (14 years difference), Mariah Carey and Nick Cannon (11 years), Hugh Jackman and Deborra-Lee Furness (13 years), Mira Sorvino and Chris Backus (14 years). So the real question here is not, “Can it work?” but rather, “Will it last?”

Years ago, I met one such couple in Singapore. Enrique was a young teacher at one of the international schools. At 32, the Chilean-born man had the gorgeous looks of a typical South American charmer. He had graduated with a Master of Mathematics degree from M.I.T. and was thrilled with his new posting in Asia. Ornella was 47 but looked younger. Of Sicilian origins, she was exotic and extremely sensual. A single mother of two boys from two different ex-husbands, she had been living in Singapore for a few years, while successfully managing her own dance school.

For Enrique, everything about Ornella was different from his world. Nothing about her compared to the young women he was accustomed to dating. Educated and cultured, the ex-dancer spoke five languages and had lived in seven different capitals. “Sophisticated doesn’t even begin to describe what this woman is all about,” he would say about Ornella.

She opened up an exciting world to him with her connections and globetrotting friends. But as the years went by, things began to change. Despite their chemistry, Ornella became possessive and insecure. If Enrique harmlessly flirted with a younger woman or even just spoke to one, it would send Ornella into a rage. Ornella also had difficulty keeping up with Enrique. He would stay on at parties much later than she and would come home in the wee hours.

The subject of children would sometimes come up. Enrique wanted children of his own one day, but he felt in no hurry to think about that subject concretely. For Ornella it was clearly too late, so the subject was often dropped as quickly as it was raised, but loomed over their heads like a menacing dark cloud.

As routine set in, it became progressively clear that their relationship had come to a standstill. Ornella saw their partnership as something for the long term, while Enrique just couldn’t bring himself to declare that she was the woman of his life. After years of being seen as an older woman’s “toy boy”—a term he despised—he began to struggle to keep his own insecurities at bay. Enrique longed for the feeling of being in charge. He was clearly looking for his new identity as an accomplished man. Enrique and Ornella’s liaison ended in part because he wanted children and Ornella couldn’t give him any, but also because of their mutual insecurities. Her gripping fears of losing him to a younger woman and his obsession with what other people thought of him ultimately poisoned the relationship.

However, age is not a guarantee of success. Even amongst most married people who are close in age, the divorce rate is still considerably high. Studies show that a husband’s loss of employment, as it relates to role definition, is a stronger contributor to divorce than age disparity. Experts point out that a relationship between older women and younger men may endure if they possess a few key elements.

In many successful cases, the age difference is no more than nine to 13 years and the woman is usually quite youthful looking. The couple seems to meet in the middle in terms of maturity and their life goals and objectives are very much aligned. The desire to have children or not is also mostly resolved. In instances where the woman makes more money than her younger partner, the man has the self-confidence to accept it. This situation may sometimes even reverse itself, when the man reaches his 40s and prime earning years, with the woman then having the option of taking a backseat career-wise.

Although quite rare, these kinds of relationships do exist and when they are successful, it is a testament that age is not the main factor defining a healthy relationship. As one such couple succinctly declared, “The least we have in common is our age. The most we have in common is our heart and mind. Which do you think matters most?”

*** This article was first published in Harper’s Bazaar Magazine Singapore ***