I’m a Woman in My 50s. Why Am I Obsessed with My 20s? 

This piece was written by one of our dear readers—a woman with something real to say. Each month, we handpick the best submissions for Dear Reader because we’re after that PROVOKED bite: truth, intelligence, and heart. These stories come from women our age—women who’ve lived enough to know better and still care enough to tell it anyway. Because being seen and heard matters. Because storytelling is how we stitch ourselves to one another. And because when one woman speaks her truth, another finally recognizes her own. — Susan Dabbar, Editor in Chief

As it turns out, the decades are uniquely linked. 

The salt-and-pepper-haired woman sitting next to me on the plane had her iPad propped up and a glossy show was streaming. Though I couldn’t hear anything, I snuck glances in between doing some work on my memoir and saw gorgeous 20-somethings engaged in seriously emo conversations, cavorting on beaches, and generally looking hot. Having been a depressed actress who moved into an ashram in my 20s, my life looked very different from those sexy TV characters’ lives.

A few minutes later I opened my email and saw an article from Diahann Reyes-Lane’s Beyond Desirability Substack: “I’m 54. I Still Got Sucked Into The Summer I Turned Pretty.” I realized that must be the show I was sneak-watching. Reyes-Lane wrote about how it helped her reclaim a wild part of her younger self she’d left behind. Apparently I’m not the only middle-aged woman transfixed by the emotional chaos of her 20s.

It’s everywhere.

Mimi Zeiman, MD, a gynecologist, revisits her 20-something self in a memoir about being a medical professional on an Everest climbing expedition in the ‘80s. Editor Sari Botton published an article about her life in the early ‘90s in which she admitted, “I’m weirdly nostalgic for those days in my late 20s, even though they weren’t particularly happy days.”

I began to wonder what really drives this midlife fixation on our 20-something selves. Nostalgia? Survival? A need to reconnect with the woman we left behind? Maybe it’s all of that—and something deeper. The more I talked with other women, the clearer it became: The decades are linked in ways that feel more deliberate than random.

The Time Is Ripe

Columbia University clinical psychologist Cecilia Dintino, PsyD, connects the two decades by what psychologists refer to as developmental tasks. “A woman in her 20s is generally and developmentally creating herself. A woman in her 50s is often met with uncertainty, change, and a need to perhaps redefine oneself,” Dintino said. “Maybe looking back is the first step to moving forward.”

The idea stuck. I’d been secretly berating myself for writing a book about my depressing 20s when I felt I should’ve spent time writing a business book for my career. But now it made sense. What if all this nostalgia isn’t regression, but rehearsal for our next chapter?

However psychologically significant, this reflection on youth is a luxury. Some women in their 50s are working double shifts to stay afloat, or are raising their grandchildren. But for women who do have the time, the 50s seem to be the decade when we heed the last call for our younger selves to be healed.

Some women’s reflection comes by memoir or journaling. For others, playlists, fashion trends, or old novels. For Zeiman, it was a way to catch up with herself. After getting married and raising a career and family in her 30s and 40s, in her 50s, Zeiman felt “like I finally had the time and space to reflect on earlier life.”

For Reyes-Lane, her obsession with TSITP helped her reunite with a “hot mess” part of her youth that she’d cast off in favor of maturity. For Botton, the 50s are a time of reckoning with regret: “I think we all reflect back on our 20s … because those are the years when you begin to establish yourself as an adult, and you make decisions that are very difficult to either reverse or rewrite.”

Maybe that’s the real draw: the option to revise.

Looking Back to Find Our Future

Sometimes revising, or as Dintino might say, revisioning, is exactly what is called for.

She works with many women in midlife and believes that after establishing a career, raising kids, and maybe having had a couple marriages, women in their 50s have a difficult time envisioning their next steps. “Where we were once creating identities with a pictured life trajectory, we now stare at the empty canvas of our future,” Dintino said. “This quest requires imagination, flexibility, and … often a revisioning of the past.”

Looking back to make new decisions as we move into the second half of life isn’t just psychological, but part of a neurological process, explained Daphna Shohamy, a professor and memory researcher at Columbia. “By remembering past experiences or by combining memories to form new situations in our minds, the hippocampus can provide potential options for the brain to try out,” she said.

We think we’re reminiscing. Really, we’re reprogramming.

I may still feel self-conscious about my low-hanging boobs in a bathing suit, but I know who I am now—and how to better navigate life’s ups and downs. Looking back wasn’t nostalgia; it was preparation for what comes next. A rehearsal for reinvention.

I realize that spending time rummaging around my 20s wasn’t just a self-involved exploration wrapped up in art, but a necessary step in creating a future—one that might be the best chapter of my life.