Darcy Dates: A Single Mom’s Hilarious Dating Diary in New York City

by Jena Kingsley

Darcy Dates is a hilarious and unfiltered dating diary based on the popular 2010 blog of the same name. Written at a time when people clung to their BlackBerrys, Instagram didn’t exist, and there was no debate over whether or not skinny jeans were cool. They just were. Seven years of marriage, one child and one divorce later, Darcy finds herself back in the dating pool of New York City. Only things were different. She was a single mom living on the Upper East Side, navigating dating as an adult, where people carried more baggage than any bellhop at the Pierre could handle. One night, alone in her room, she began to document her dates in the form of a blog. The blog became her diary. This book is her diary. Darcy Dates is the perfect balance of comedic, cringey and touching. You will belly laugh, you may tear up, you may want to look away at times. Most importantly the reader will be cheering Darcy on in her quest for love. But over time she starts to wonder… maybe it's not love she was looking for all along. Maybe she was just looking for herself. Names and locations have been changed to protect the innocent.

399 pages, Kindle Edition

Published June 3, 2025

About the author

Jena Kingsley is a New York City native, comedian, writer and viral sensation known for turning modern life’s quirks into comedy gold. Her social experiments, like posing as a Starbucks bouncer or enforcing a “No Selfie Zone” in Central Park, have earned her praise from outlets like CNN, TIME, and The Today Show. The media has called her work “Genius” and “Brilliant.” A stand-up comic, podcaster, and former SiriusXM regular, Jena’s quick wit and bold humor have made her a standout in the comedy world. She’s also written for various publications and brands, using her sharp observations to expose the absurdities of everyday life.

Reviews

[Sue · Rating 5 out of 5]

Kingsley has a knack for humor and it shows in her debut book "Darcy Dates." Witty and hilarious, I enjoyed all of "Darcy's" dating stories. Some were very relatable and others shocked me. A great summer read!

[Ebb · Rating 5 out of 5]

I mean WOW! This book had me straight peeing on the floor. Was lucky enough to get an advanced copy and you all will be so lucky in a couple weeks when YOU TOO can be blessed with this deeply personal comedic experience.

[natasha fishkin · Rating 5 out of 5]

Loved this book!

Darcy’s voice is funny, relatable, and sharp — Jena brings each date to life with a mix of humor and honesty that makes you feel like you’re right there beside her, cheering her on (and sometimes cringing with her) through every moment. Some of the stories had me literally laughing out loud and others are touching, offering a thoughtful glimpse into putting yourself out there. It’s the book you’ll want in your beach bag and recommend to all your friends.

[Jenifer Minikes · Rating 5 out of 5]

This book is amazing! I couldn’t put it down. Jena is a fantastic story teller with an amazing mix of humor and authenticity. It’s a must read!

[Steven · Rating 5 out of 5]

Jena is absolutely brilliant. I got an advance copy. Her writing is so great she will make you think you are there in the room. Every scenario is hysterically funny and there are so many touching moments. This book is a must read. Her POV makes her comedy outstanding.

[Claire Rose · Rating 5 out of 5]

If you are looking for the perfect hilarious beach read, or actually, anywhere read, then Darcy Dates is for you. Brilliant, hilarious, but most importantly, real. As someone who met their other half in college a billion years ago, Jena’s (or Darcy’s) window into the world of dating post-divorce had me rolling - and sometimes cringing. And of course…Robbie!!!

[Alana · Rating 5 out of 5]

So so funny and a true time capsule into 2010-2012 era

[Rachel · Rating 5 out of 5]

This book is a must read! It is a definite page turner. This book is so funny and so descriptive. The book follow Jena aka Darcy, through her hilarious dating days. Must read summer beach/pool/anywhere book!!!!! Highly recommend!!!

[Lara · Rating 5 out of 5]

Darcy Dates is an absolute gem. Jena takes her readers on an hysterical, touching, sometimes odd but always real ride through Singletown. Single, coupled, complicated? It doesn't matter. Darcy Dates is for anyone who has or will hurl themselves into the abyss of looking for love. More than anything this book is a prescription to say YES to whatever opportunities life gifts you. Even bad dates have silver linings- usually in the form of friends and family there for every high, low, in between & Robbie. (Once you read the book, you'll know.)

[Susan Rothman · Rating 5 out of 5]

A fun read…Darcy lets you into her personal life as a single working mom, her relationship with her own mom, and being out in the world of dating. She has a great sense of humor in an endearing way. Sweet story!

[Ronnie Agress · Rating 5 out of 5]

So funny!!! I loved every minute of it and was sad when it ended. I wanted more.
I got an early copy
Loved it