I was even inspired to write a book about it.
The trail was quiet except for the crunch of my boots on the rocky gravel. I had just started my usual solo Saturday morning hike when suddenly, a burst of laughter escaped my mouth. I’m not sure where it came from, but there it was: a bizarre, distant memory of a man I dated in my 20s. He was a strange one, whose words were almost as baffling as the relationship itself.
On one of our first dates, he looked at me from across the candlelit table and asked, “So, do you have more hair on one side of your head?”
My hand instinctively brushed my part. “No,” I said, forcing a smile. “That’s just how I part it.” I reached for my glass and quickly steered the conversation in another direction but his odd question lingered like an uninvited guest. It was unclear if he had been genuinely curious or simply making a bad joke, either way, my just slightly off-centered part was as unremarkable as they come.
That moment became a snapshot of our entire relationship: clumsy and mismatched. I wanted him to be “the one,” so I ignored the nagging feeling that we didn’t quite fit. I was still in college while he was already years into a successful career. I wanted a future with a family; he wanted to stay unwed and childless forever.
But on that trail, nearly 25 years later, it wasn’t just his comment that made me crack up. It was me—young and hopelessly hopeful, some might say naive—pretending the weirdness wasn’t there, thinking maybe, just maybe, everything would somehow all fall into place despite the red flags.
It turns out I am not the only person who has heard something outlandish on a date—whether it happened 20 years ago or just last week. When I shared my ex’s strange comment with friends, it opened up a treasure trove of dating absurdities. Some were insightful while some made me say, “Are you kidding me?” out loud. Some sparked more memories of my own, like how a guy told me on our second date that he wished he didn’t have a girlfriend.
I even have some memories from dating my own husband, who I will be celebrating 20 years of marriage with this year. While nothing he said was outrageous enough to be memorialized in print, we’ve definitely had our share of awkward moments. Like when we first met during my college internship, and he playfully called me a slacker before I could explain I’d taken a semester off to grieve my mother’s unexpected death. The sheer terror and regret that washed over his face and how he showered me with apologies after told me everything I needed to know about him.
Then there was the time months later in his condo when he told me he loved me, and I responded with a softly spoken “thank you.” His hands were cupping my face, covering my ears, and though I knew he said something sweet, I didn’t want to ruin the moment by asking, “What?” Later, when he summoned up the courage to say it again, I reciprocated, and he asked why I hadn’t the first time. That’s when we realized my mistake, and I found myself showering him with apologies.
What made me fall in love with my husband was a mix of qualities I hadn’t found in past relationships: humor, kindness, trustworthiness, and centeredness. But after 20 years of marriage, I do sometimes wonder what it would be like to reenter the dating scene; to experience the excitement of meeting someone new and getting a peek into their world. But do I miss all those awkward moments?
A friend once theorized that you marry the best person you can land at the time, but when that’s no longer the truth, it’s time to reconsider. While I’d be lying if I said I didn’t miss dating, my marriage offers its own kind of excitement: stability, teamwork, and deep connection. My husband and I joke that marriage should be on five-year terms, where at the end, you decide to renew or part ways. I’m happily renewing for another term; I’ll just have to live vicariously…
After hearing all the ridiculous dating lines my friends have been served over the years, I felt compelled to collect more. So I launched a website and invited others to contribute their own stories. At first, I wasn’t sure how it would go, but then, submissions from strangers started pouring in—each one felt like a small gift—so I decided I should compile them into a book. If something made me laugh, sigh, cry or cringe, it made the cut.
In the end, just over 100 verbatim lines made it into the book, each paired with backstories, lessons learned, or a touch of dry dating advice. Like any trial-and-error process, dating brings moments of exhilaration, disappointment, surprise, and in many cases, true befuddlement. It can uncover truths about yourself in unexpected moments, with each experience bringing clarity about what you’re truly seeking—and you’re bound to meet some very “interesting” characters along the way. This book is about finding humor in all this chaos. Here is a sneak peek:
Get your own copy of The Things I Heard While Dating.
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by Emily O’Brien
Emily O’Brien is the author ofThings I Heard While Dating, a compilation of over 100 verbatim lines contributed by people worldwide, exploring the often awkward and relatable moments of modern dating. A Raleigh-based writer specializing in wellness, lifestyle, travel, architecture, and personal and professional development, Emily serves as the managing editor ofSUCCESSmagazine.She misses the simplicity of the early ’90s when she only cared about listening to her Walkman, wearing her Blossom hat, and drinking a Snapple.
