Ever walked away from a date or a partner, not knowing whether to feel baffled or amused by something that was said? Emily O’Brien knows exactly what that feels like—so she decided to turn it into a book.
Things I Heard While Dating is a collection of over 100 hilarious, awkward, and downright bizarre one-liners from real-life dating experiences. From cringe-worthy pickup attempts to jaw-dropping moments in relationships, this book showcases the funny and outlandish things people say when they’re trying—and sometimes failing—to make a connection.
I recently caught up with Emily, the Raleigh-based writer behind the book, to learn more about how this quirky project came to life.
“It all began as more of an art project than a book,” she shares. For years, Emily’s been a self-proclaimed "compilation lover," someone who gravitates toward groups of things, lists, and quirky collections. It was this love of compilations and a memorable one-liner from an ex that sparked the idea for Things I Heard While Dating. The line stuck with her, and she figured others must have similar stories.
It wasn’t until Emily was on a road trip from Boulder to Raleigh with her husband and daughter that everything clicked. As they drove, she realized: this needs to be a book. After settling in Raleigh, Emily launched a website where people could share their most outrageous dating lines. Thanks to her involvement with CreativeMornings, a non-profit spotlighting perspective art that month, her site gained traffic, and as submissions poured in, Emily knew she had a book on her hands.
For Emily, the entire process felt more fun than work. “I spent my ‘off-hours,’ weekends, and holidays just marinating in the project,” she says. What started as a hobby became something much bigger, and Emily enjoyed reading through the submissions. The toughest part? Narrowing down to just the right ones.
Emily explains that the book is meant to be lighthearted, like “a piece of candy.” It’s not about bashing others but about sharing a laugh and connecting over our universal experiences. “I want people to escape for a bit,” she says. “My goal is the book helps you laugh and feel good, whether you're reading it alone, with friends, or at a dinner party.”
Despite the absurdity of some stories, Emily’s perspective on dating hasn’t changed much from her experiences 20 years ago. “Things are different now, but dating is still about testing the waters,” she says.
Looking for a laugh or a Galentine’s Day gift? Things I Heard While Dating is the perfect read. If you’ve got a wild dating story of your own, Emily invites you to share your piece at ThingsIHeardWhileDating.com.