Things I Heard While Dating

Because who doesn’t love a good cringe…

Dating is not for the faint of heart—clearly. Sure, you could meet your soulmate, but, more often than not, it’s a series of embarrassing encounters, awkward silences and, well, riveting stories. Enter Things I Heard While Dating, a global compilation of cringeworthy, unfiltered dating snippets.

“The idea of this book originally started when I remembered something strange an ex had said to me,” reflects local author Emily O’Brien, “and how much in awe I was of my early-20s self that still dated him for a very long time after that. I started asking some friends if they had awkward lines too—and, boy, did they deliver!” 

O’Brien began by gathering a handful of dating stories for a quirky, mixed-media art project, but after some work on it, the idea didn’t take. Then, on a road trip during her family’s move to Raleigh, she realized a book would be a better fit. 

From there, the anthology concept crystallized, and she launched a website for people to submit stories—with the option for incognito submissions to encourage contributions without fear of recognition. 

The verbatim selections that automatically made the cut garnered a laugh, gasp or sigh—coupled with behind-the-scenes stories and dating advice. And rest assured there’s plenty of jaw-dropping fodder for a sequel. thingsiheardwhiledating.com

I can’t get you out of my head. They just don’t make women with birthing hips like yours anymore,” he said as she returned from the bathroom. When she broke up with him, he retorted, “I have money if that helps.”
L.S. | Riverhead, NY
First in-person date post two video calls

Fine. If you’re not going to sing karaoke, I’ll just take you home,” he said following a sushi bar-turned-karaoke they had no plans to attend.
Gwen | Boulder, Colo.
First date

Whenever anyone hears something from my past, they never want to speak to me again.” She googled him years later and found him on To Catch a Predator.
Anon. | San Francisco
First date

Hey, how about you give me a ring?” She said despite no previous chat on marriage.
Guy | Devon, England
Dating several months

I find you being a vegetarian so sexy. I want to eat edamame off your back.” Said while making out.
Abby | Lenexa, Kan.
Second date

If you are ever hot at my house, just know you can take your shirt off, and it’s totally fine,” They said, not keeping things cool.
Anon. | Boulder, Colo.
Two weeks in

Oh, did you need something to eat?” After he asked her to dinner.
Sarah | NYC
Second date