I'm A 28-Year-Old Woman With No Dating Experience—Should I Be Stressed?

probably not

Hey y’all,

I’m in Mexico City for the 5th (maybe 6th?) time. I love this city. I’ll be sharing my fav things to do, where to party, eat, and shop over on my personal Substack soon.

There are 6 of us here, and all of our dinners have been filled with heated debates around politics, pop culture, and social commentary. It’s been both thrilling and enlightening, but also exhausting. I’m learning that my friends have some very different views on topics I stand firm in, and we’ve had to defend ourselves but also be open to new ideas and other points of view that are in complete contrast to our own.

This may be a hot take, but as Black women, we’ve put a higher stock in protecting our peace and “doing us” in the past few years so much so that the worlds we’ve created tend to look the same: same ways of speaking, same ways of styling ourselves, same brands we support, books we read, etc. But at what cost? When someone expresses something that is in direct contrast with how we view the world (minus the isms: racist, sexist, xenophobic, and all that), do we create space or shut it down?

In a contentious interview with Trevor Noah, Chimamanda Ngozi Adichie argued that you should prioritize befriending people you disagree with. She spoke about growing up in Nigeria, a place of 'manyness'—many ideas, many different people—that you get along with even though you may have different views on life, and how Americans are growing less tolerant of that concept. While I agree with her, after these conversations I’ve realized that I’ve surrounded myself mostly with “sameness” instead of “manyness,” and though lowkey irritating, it’s been refreshing to feel challenged by my friends in this way.

Do you surround yourself with people of like minds or diverse minds? Do you like to be challenged in your ways of thinking by your friends, or enjoy the comfort of agreeing on most things? Let me know in the comments!

This Week’s Story

Is it just me, or are people quietly quitting dating? I see more women online talking about personal development, self-care, and hobbies than dating these days, and while I love it for the girls, what’s the larger trend here? In this week’s essay by Tabby Kibugi, a returning writer for Carefree (yasss!), Tabby gets into her lack of dating experience and how it’s affecting her ability to fully show up in her friendships, battle the aunties, and feel “normal.” Let’s get into it!

Take care,

Anayo Awuzie
EIC of Carefree Media

I'm A 28-Year-Old Woman With No Dating Experience—And That's Okay

by Tabby Kibugi

A few weeks ago, I attended a wedding with some high school friends I hadn’t seen in years. After catching up on work and lamenting on how hard the economy was hitting our pockets, our conversation drifted to relationships and marriage. My best friend, Wambui, from high school, gushed about her upcoming wedding and how she was trying to keep it small, another shared that she was expecting her first child, a girl, while the rest chimed in with updates on their long-term partners. When it was my turn to share, I hesitated. What was I supposed to say? That I had no grand love stories to recount? It felt like an awkward confession, especially at a joyous occasion like a wedding. Instead, I joked about being the chronically single friend and quickly steered the conversation elsewhere.

At 28, I’ve never been in a romantic relationship. No whirlwind love stories, no exes, and no dating horror stories to share in WhatsApp group chats. Whenever I mention my lack of dating history to anyone, it often elicits mixed reactions. Most assume I’m lying, others are convinced that I must be extremely pious, while the rest conclude that I’m just too picky. None of these are true. And while I’d like to blame my lack of dating experience on my reserved African culture, where dating iss rarely openly discussed except in vague, euphemistic questions like "Do you have a friend?" I know that’s not entirely it.

My lack of dating history is also not due to a lack of opportunities. In reality, I’ve always had a bustling social life. I’ve met plenty of people both in and out of work, I’ve been in social circles, and I’ve had my fair share of crushes. However, none of my platonic relationships have led to any sort of romance, and I’ve learned to be okay with that.

Growing up, I always assumed that dating was an inevitable phase of life. Like learning how to drive or getting your first job, dating seemed like a milestone that everyone would naturally reach at some point. The romance movies I watched and the casual conversations with my friends all painted relationships as an essential part of life. So when my teenage years passed without a single romantic experience, and then my early and mid-twenties, I began to question whether there was something inherently wrong with me. Was I too awkward? Too unapproachable? It’s a quiet insecurity that I’ve carried with me, one that has made me feel like an outsider in conversations about love and relationships with my peers.

For a long time, I let this insecurity dictate how I felt about myself. I believed that being single at 28 was an embarrassing secret to keep hidden. But over time, I’ve begun to reframe the way I looked at my situation and whether my relationship status should even define me at all.

We are living in a time when dating norms are shifting and more people are rejecting the idea that being single is inherently tragic. According to a Pew Research February 2022 survey, 56%of single adults are not looking for a relationship or casual dates. The majority of single adults who weren’t looking for a relationship cited enjoying being single (72%) or having more important priorities (63%) as minor reasons. At the same time, a growing number of women on TikTok are openly discussing their lack of romantic history and how they’ve learned to embrace it, with the hashtag #neverbeeninarelationship garnering more than 50 million views.

In one TikTok video, a woman by the username, kishapeart, explains how she had never been in a long-term relationship until her mid-30s. “I’m so glad that I found my person in my mid-30s because it helped me to stay true to who I was. I got clear on what I wanted in a partner, and I do not listen to the naysayers,” she said.

According to Dr. Patricia Dixon, a licensed clinical psychologist and relationship counselor based in Tampa, Florida, there has been a cultural shift toward embracing singlehood, reframing the narrative around being single as a choice rather than a circumstance to endure. “As more individuals share their stories online, it creates a ripple effect, encouraging others to express their own journeys. Traditionally, society has placed a premium on coupledom, but many are now finding joy and fulfillment in friendships, career pursuits, and self-discovery.”

But despite the growing acceptance of singlehood as a valid response to the chaos of modern dating, being an African woman at 28 who has never dated still comes with deep-rooted stigma and pressure to settle down and start a family. I come from a culture that has placed a strong emphasis on marriage and family as key life milestones. I’ve had to face numerous questions from African aunties who find my lack of dating history both baffling and deeply concerning. Their concern isn't just about companionship. It's about tradition and, in many ways, validation. In their eyes, a woman who reaches a certain age without a husband or at least a long-term partner is an anomaly in a culture where marriage isn’t just a milestone but an expectation. By my age, most of my African aunties were long married with one or two children. By their standards, I’m very behind in life.

“The reality is that there’s always a weight of societal and familial expectations regarding traditional dating and marriage timelines that many Black and African women face,” Dr. Dixon explained. “For those Black women who do enter the dating scene later in life, dating can feel even more complicated, and it may come with a host of unique challenges.”

It’s not just me — many African women know this struggle all too well. In the book, Yinka, Where Is Your Huzband?, Yinka’s aunties and mother constantly push her toward marriage, convinced that her life is incomplete without a husband. And while I’ve never gone as far as creating a 'husband hunt' plan to appease my family as Yinka did, I’ve had my fair share of awkward conversations where I’m reminded that, at 28, I’m running out of time. Like Yinka, I once thought my lack of romantic history was something I needed to fix, but I’m realizing more and more that it isn’t a problem at all.

So now, I’m just letting things be. Being single at 28 is just the way my life has unfolded. I've stopped thinking of my lack of dating history as something that defines me but rather just another part of me, like how I’ve never been on a train or watched a sci-fi movie. I'm no longer compelled to rush into a relationship simply because I feel like I’m falling behind. If love comes along one day, great! But if it doesn’t, that’s fine too. I don’t need a relationship to validate my existence or prove that I’m worthy of love and happiness.

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Tabby Kibugi is a journalist and content writer who mainly covers health, lifestyle and social justice stories. Her work has been featured in Insider, Refinery29, Flo Health, Buzzfeed, Metro UK, Reader's Digest, Anti-Racism Daily and more. She is also a regular contributor to Black Ballad. You can find her on Twitter or read more of her work on her portfolio.