100 Books Like My Year of Really Bad Dates

I rarely see a book cover the dating world from this author’s vantage point: as a long-married woman entering the dating world after 25 years with an “I’m open to anything” attitude, yet with the gravitas and insight of a successful Manhattan psychotherapist.

Her forays into the worlds of polyamory and swinging made me go, “Wait! Stop! Go home!” Her bravery and vulnerability left me breathless. But then I realized that to find intimacy, those are the very qualities you must marshal.  Equal parts action-packed and introspective, the book gave me the tools to look at my own social life. 

In this boldly candid memoir, Lyz Lenz chronicles her escape from a marriage missing mutuality and respect only to discover the same phenomenon at play in the dating market.

I felt less alone in my shock at what men say to me on dates when I read what dates said to Lenz, a beautiful, successful writer: “If you want to be with me, you’ll need to be a better cook,” and “your professional accomplishments are not as impressive as my dick.” 

But ultimately, what I liked best about the book is Lenz’s hard-won conclusion – to never again lose herself in a man.

Williams proves an engaging storyteller as she takes us through the slings and arrows of her marital breakup and subsequent foray into dating.

What I liked best was Williams’ admission that, in writing her debut memoir, she had to learn an entirely different language, translating her complex web of emotions and experiences into the written word. So, Williams’ prose carries a “riding this horse for the first time” giddiness, freshness, and fearlessness.

As a journalist accustomed to objectivity, I, too, had to learn a new language of subjectivity, penning my first memoir.  Williams served as a role model for me as I made this difficult transition.

This collection of personal essays, culled from 8,000+ submitted each year to the New York Times “Modern Love” column, absolutely sings!

What I liked best about this book of true stories about love is the revelation that everyone is inherently a storyteller.  That’s because conflict is part of everyone’s life, and conflict, by definition, equals drama.

How revelatory to witness an artful 1,000 words woven out of the day a woman’s flirty email to her new beau is not answered, at least not right away. Also, I loved the writing style of each essay, as if the reader is eavesdropping on two friends telling it like it is over a cup of coffee.  

Wine and magic. Need I say more? No, but I shall anyway: I love wine, complex and delicious and delightful; and I love magic, mysterious and powerful. Laura Anne combines these elements to great effect in her Vineart War series, where spells are crafted from wines—the only source of magic in the world. It was hard to read this without wanting a glass of pinot noir by my side!

This is a voyage of stories about wine from the old world and new world, some very amusing.

Nathalie travels to Burgundy to explore Pinot Noir, Champagne to learn about sparkling wine, California and Australia to learn about New World wine, and many more places. Through her exploration you’ll learn about the wine regions she visits and about wine tasting.

This book is written in a very easy and humorous style, as hinted at by the title. I loved this book for its unstuffy, friendly approach to wine. 

Fifteen Minutes to Live is like a darker, more intense version of 50 First Dates. In the novel, 36-year-old Carl discovers that his high-school sweetheart, Jesse, is losing her memories of recent events every 15 minutes, compelling him to weed through a web of secrets to find out the truth about her. Carl is a genuine and relatable protagonist whose imperfections are a breath of fresh air. He’s self-deprecating with amusing quirks (like trying to befriend a raccoon), and his love for Jesse, though not always noble or logical, is fierce and moving. Likewise, Jesse manages to shine with strength and determination, despite the fact that her memory resets every 15 minutes. I’m also a fan of the intense “up against the clock” storyline, which offers great edge-of-your-seat moments.

Before reading On Writing and Writers by Margaret Atwood, I naively believed that writing about writing was necessarily boring. Like a textbook, full of cold, mechanical steps to improve. Atwood’s book proved me incredibly wrong. 

I was mesmerised by Atwood’s self-deprecating charm and disarming wit, and saw myself in her initial query about whether she has the right to write – namely, the right to make grand claims about her practice.

Perhaps what I loved most was her reluctance to offer anything concrete. She dances near a decision, a position, an answer, and then just as quickly, she turns away again. Self-indulgently, I enjoy the idea that writing is a mystery that doesn’t have one answer and that can’t be pinned down. For me, Atwood’s book confirmed this fanciful notion. 

As an inveterate and wildly ignorant amateur birdwatcher, I couldn’t resist giving this book a try.

I found it at my local library. The very title seemed to mirror much of my own poetry, an unexpected synchronicity that called my name, and its contents exceeded expectations. 

This book is deeply personal without being self-involved. Although the author possesses a depth of knowledge about birds I will never approach, his humor and self-deprecation make the book as accessible as it is mind-blowing. Like a poet, Knapp offers us vignettes whose tiny glimpses manage to mirror the whole universe.

Who hasn’t looked at a raven riding columns of air and ached for that perfect freedom of flight? Though we’ll never know the skies as they do, we can still learn so much from our feathered neighbors – about the world, about ourselves, and about what sort of magic is real.

This is, hands down, the single funniest book I have ever read. What’s amazing is that in addition, it’s really a heartfelt memoir. Harrison Scott Key can take contentious family relationships and use them to simultaneously make your heart ache and your face hurt from laughing so much. He’s also skilled at self-deprecating humor, unabashedly highlighting his own flaws throughout his story. The title refers to the author’s father and the book chronicles interactions from youth onward—all the cringe-worthy moments when a parent and child simply cannot see eye to eye (and you can tell they probably never will). And yet the undercurrent of love throughout is what brings in the heartache that balances out the hilarity. Again, this is the single funniest book I have ever read, and that should count for something!