I'm 27 and Divorced—Here's What My Dating Life Is Like

The sweet, attentive guy sitting across the table from me smiled, eyeing the room as our rapid-fire date-two banter quieted for a moment. Taking the lull by the horns, I decided to get it over with and in one swift breath said, “I should probably mention, I’ve been married before.”

I braced myself, waiting for some variation of the surprise, confusion, and pity super pack I’d come to recognize. “Wow,” he said. “But it doesn’t seem like anything is wrong with you.” There wasn’t a date three.

People say that your twenties are for exploring what you like, what you want in life, and who you want to spend that life with. I, apparently, didn’t get the memo. By the age of 22, I was married to my college boyfriend and building a home with him in New York City. While my friends were flirting with hot strangers in bars, I was opening a joint bank account. While they were making sense of the still-unsaved phone numbers ghosting and bread-crumbing them, I was discussing when my partner and I wanted to start having kids. Dating was an alternate reality I knew of only as an observer, watching the show from my comfortable couch of wedlock. I was a bystander to the emergence of dating apps and the harsh reality of the left swipe, and everything I knew about dating came from my friends’ romantic (and more often horrific and hysterical) stories.

That all changed when my marriage fell apart and I found myself divorced at 27 and facing the adult(ish) dating scene for the first time ever. Dating has most accurately been described to me as going on a job interview for a position that you aren’t really sure you want: exciting, nerve-wracking, and frustrating all at once. And I did not have the first clue about how to navigate it.

There was the larger, existential piece of it: How could I open myself up to another person after I’d made promises about forever and seen them go up in flames? How could I feel intimate with a perfect stranger after living with a different man my entire adult life? How could I know what I’m even looking for in a partner after I’d been proven so wrong before?

And there was everything else: Did I want my date to pick me up (chivalry!) or meet me at the bar (safety!)? Was I supposed to offer to pay or fumble awkwardly as the waiter dropped off the bill? The mind-numbing first-date questionnaire was confounding. What could I ask that’s charming, not too intense, and actually revealing? I recall being stumped when a date inquired about my favorite color. Did he mean my favorite color nail polish, my favorite color to look at, my favorite color to wear, or my favorite color to paint the walls? (The date ended fairly quickly.)

Even more puzzling was the decision of whether and when to mention my failed marriage. Try this for small talk: “No way, I love Stranger Things too, and fun fact about me—I was married not too long ago.”

Getting divorced felt a lot like getting a rug pulled out from under me, and dating was the uneven cobblestone under that rug. The swiping, the profiles, the post-date texting rule book replaced every answer I thought I had with a thousand questions. But after a period of post-marriage grieving, I knew I still believed that there was a better side to love and relationships than what I’d experienced. So I plastered on a smile and dragged my heels (chosen via frantic snapshots texted to a friend) to date after date.

And with time, I started feeling less uncertain. While I was married, I never thought to question the simple things. Sure, I considered my preferences in the context of my marriage: Where did we want to live? How did we want to spend our time together as a couple? What was our favorite Sunday brunch spot? But I stopped asking the questions that characterize who I am: What is on my bucket list? What are my favorite hobbies? What does makes me feel accomplished? What I discovered while dating is just how little I knew about myself, not as someone’s wife but as a 27-year-old independent woman. Ironically, looking for someone else helped me get to know myself and focus on constructing a life that I found fulfilling. I started to see how my experiences, even my failed marriage, enrich who I am and what I bring to the table. I started knowing the answers to all the cliché questions that once made my head spin—and some of the deeper ones too.

So much of the healing process came through meeting other people and getting a better understanding of a universe outside of my own. There was the date who introduced me to meditation (and, for a second, had me convinced I should go to Burning Man), the date whose sharp comments made me question my take on religion, and the date who asked me point blank what I needed in life to be happy—making me realize that I didn’t actually know the answer. I’ve been on dates that have inspired me and enlightened me with new perspectives on matters I would never have thought I’d consider or reconsider, and dates that confirmed what I’m definitely not looking for. Some dates reminded me of why my marriage didn’t work and forced me to stand up for what I believe in. The best dates gave me an appreciation for the chance to figure out who I am, on my own.

Still, I can’t say I ever feel completely comfortable breaking the news that I'm divorced. It’s hard to predict how people will react and how their reactions will affect me. But through that discomfort, I’ve grown to trust my own judgment of character and pushed myself to be choosy about the people I let in. I have found that nothing fine tunes your bullshit radar quite like the uncomfortable moment after you reveal something about yourself. And in that sense, dating as a 27-year-old divorcée has completely dislodged me from the comforts of the only life I knew and made way for me to construct one I love.

By the way, my favorite color is maroon.