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Single, successful and still not enough
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All Woman, Relationships
 on June 30, 2025

Single, successful and still not enough

ALAISHA THOMAS 

DERRIE-ANN is 34, single, child-free, and the proud owner of an online boutique that offers skin and health care items to women all across Jamaica. Online, her business is booming.

On her personal page, she preaches the mantra of the soft life, travel, and no stress, being content to sip mimosas, travel the world, and wear the finest, unencumbered by man or child.

Her DMs are filled with women asking for business tips and skincare routines, and men asking her out. But offline, it’s a different kind of message.

Her family has been asking over and over, “Yuh not afraid to get old and have nobody to tek care of yuh?”

At church this past Easter, an old school friend uttered, “Mi hear dem independent woman deh always crying inna dem bed alone at night.”

Her ex — now married with two kids — once messaged her, “You’re always shining online, but when yuh going to settle down? You’re getting up in age.”

It’s always subtle, never cruel. Just constant. A thousand tiny reminders that no matter how many people like her posts, society still views her life as unfinished without a husband.

Counsellor Annette Palmer-Lowe says this experience is the kind of slow, grinding tension that success can’t cure for women — the feeling that though they are visible and powerful, they are still out of place without a partner.

“So a woman can build a platform, a brand, but it doesn’t shield her from the unspoken currency of respectability still rooted in marriage,” she said.

She said for many women, building a brand by themselves is okay when they’re younger, but once they hit 30, the questions start, both from the young and old, about whether they’re not afraid to live life alone.

“Sometimes I’m afraid that people can’t see how full my life is unless I’m sharing it with a man,” said 40-year-old senior teacher Elizabeth, who has a master’s a house and car, “but not the important things, which are a husband and children”.

“I’m married to peace and engaged to growth, but not many people can accept that,“ she said. ”Even in situations where my achievements are admired, it’s often followed by the question of who is helping me build, and the question, ‘so no man yet? With all your success?’

“Then there are the people with the pity smiles, especially those who are married, like they pity the unmarried,” she says.

Said Palmer-Lowe: “The real challenge is getting society to see a woman’s wholeness without a wedding band. And though many people may think that it’s 2025, and those things don’t matter anymore, the fact of the matter is that they do, because that’s one area of tradition that has continued to withstand the test of time.”

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