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Sex with Shakespeare: Here's Much to Do with Pain, but More with Love

4.17  ·  Rating details ·  584 ratings  ·  138 reviews
A provocative, moving, kinky, and often absurdly funny memoir about Shakespeare, love, obsession, and spanking.

When it came to understanding love, a teenage Jillian Keenan had nothing to guide her—until a production of The Tempest sent Shakespeare’s language flowing through her blood for the first time. In Sex with Shakespeare, she tells the story of how the Bard’s plays
Hardcover, 334 pages
Published April 26th 2016 by William Morrow
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Average rating 4.17  · 
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 ·  584 ratings  ·  138 reviews

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Start your review of Sex with Shakespeare: Here's Much to Do with Pain, but More with Love
This is a modified version of the review that originally appeared on my blog, Shoulda Coulda Woulda Books.

Time on to-read list: A few months

Reason for hesitating to pick up (in the form of an internal monologue): "Ooh, that interview was great, I really want to read that, on the list it goes! Oh wait.... won't that make me look weird for wanting to read that? I don't know.. maybe it's all really narcissistic and stupid anyway... I'll wait... I'll wait. Oh wait, there it is at the bookstore. No
Jan 22, 2016 rated it really liked it
Not for the uptight or conservative! (So, fine for me.) SEX WITH SHAKESPEARE is a rich and thought-provoking read. Jillian Keenan's writing is wonderful, her spirit intelligent and funny. What I enjoyed most of all about her memoir is how she shares her path towards vulnerability and intimacy with (first) herself, and (then) with her romantic partners. I appreciated this very much, and found this part of her memoir was the universal message, transcending her personal story of coming to terms ...more
Apr 26, 2016 marked it as to-read
Recommends it for: my brain
And now someone's written a book analyzing her spanking fetish through Shakespeare. It's like putting pie on cake.
Viktor Quinn
Dec 11, 2015 rated it it was amazing
Shelves: non-fiction
This book is brilliant. Really.

Reading about how someone else thinks about sex and lives sex - especially someone so unassumingly honest - is touching.
Reading about how someone got over insecurity of the deepest kind is uplifing.
Reading about how someone leared to live better by conversing 300+ year old characters is the dream of every bookworm.

re. sex - I felt like when a good friend, at the end of a long talk, looks me straight in the eye and tells me exactly what she's about. With only an
Mar 08, 2017 rated it it was amazing
I expected to enjoy this book. I expected to laugh and to learn a lot from it. I did not expect to completely fall in love with it. Yet here we are.

Most of the other reviews have covered the qualities that make this book 5-star-worthy. It's funny. It's touching. It's unflinchingly honest. It covers a lot of uncomfortable subjects with self-awareness and grace. And it taught me a lot about kink that I never knew before. Bonus points for learning something new!

But it's mostly about people. And
Emily Stearns
Jan 15, 2016 rated it it was amazing
While not wholly for the conservative, there are only a few scenes which were really out there - well, in a world where adults should be able to talk honestly about sex without blushing.

I loved this book. Keenan beautifully mixes Shakespearean analyses into her own life, sexually and not necessarily so. She taught me much about the Bard and BDSM, about life in general and love. The writing is open, honest, and riddled with humor; the serious moments strike as relatable instead of far-fetched, as
May 19, 2016 rated it it was ok
Honest, forthright...and tedious. In a minor miracle, the author combines Shakespeare with sexual kink and comes up with something tiresome.
Kent Winward
Apr 06, 2017 rated it really liked it
So what do you call literary criticism that is done through the lens of your sexual fetish? Not sure, but it is refreshing. Spank the author if you disagree -- she'll enjoy it.
Jul 06, 2017 rated it it was amazing
This book was great! I leaned so much about kink and Shakespeare! A+
Kiwi Carlisle
Apr 30, 2016 rated it it was amazing
I checked this book out because I had read an article by the author about sex and Shakespeare. I have a slight acquaintance with folks who are into S&M, enough to know that it is emphatically not my kink. Keenan's excellent writing in this book has broadened my understanding of it a bit. What I truly love, however, is her relationship with Shakespeare, how his writing informs and illuminates her life. I can identify with that. This is a passionate, well crafted, humorous and touching book, ...more
Simon Patience
Jun 12, 2016 rated it it was ok
I'm really surprised by the positive reviews. I was so excited about getting this book. I started it with enthusiasm and it didn't disappoint at first. It quickly, however, degenerates into self-indulgent twaddle. If the writer's life were a bit more remarkable or interesting then it would warrant the kind of scrutiny that the memoir gives it here. But it aint, so it don't.

Exploring sex and sexuality in Shakespeare is a worthwhile endeavour but it requires a much more sophisticated and deft
Quinn Collard
Jan 02, 2017 rated it really liked it
As both a kinky person and an English major, I was very excited about a book combining kink with literary criticism. Finding links between the two was done well, and it was interesting to hear about the writer's history with her kink. The parts about her relationships that weren't related to her sexuality bored me, and the imaginary conversations with Shakespearean characters device started to feel forced by the end, but for the most part I enjoyed this book and think it would do a good job ...more
Lynn Weber
Jun 03, 2016 rated it it was amazing
Shelves: memoir
Memoir is the genre of our age for a reason. As a culture we are just learning to confront reality, and each new story opens another window onto it. This memoir of a young Shakespeare scholar working through her sexual identity is so rich and honest and smart and humane. And her readings of Shakespeare's plays are really insightful. Thrilling, even.
Melissa Yael Winston
Nov 11, 2017 rated it it was amazing
A brave, deeply touching memoir for anyone who has wrestled with their own sexuality.

Readers who’ve ever dealt with a part of their sexuality that they couldn’t accept—that they felt somehow was “ugly” or “wrong,” who sought out books as a release from real or perceived isolation—will enjoy Jillian Keenan’s work.

Sex with Shakespeare leads the reader through intriguing and frequently heart-wrenching scenes from Keenan’s own life while interweaving them with an entertaining analysis of 14 of
Samantha Allen
Jun 11, 2018 rated it it was amazing
I usually fall asleep on planes, sometimes before it even takes off. Something about the movement makes me super drowsy. But Sex with Shakespeare is so good it kept me glued to the book on two separate late night 4 hour flights. I’ve never stayed awake on a plane ride that long, so this is really saying something. I couldn’t put it down. Sex with Shakespeare is so brave and funny and smart. Without exaggeration, it’s the most engaging memoir I’ve ever read. It somehow manages to be hilarious, ...more
Sep 01, 2018 rated it did not like it
Ick. Confused young American discovers her sexual identity as a spanking fetishist, clarified by goofy imagined dialogues with Shakespearean characters. I lost the little sympathy I had for Keenan when she described her masochistic initiation/affair with an ex-pat coke dealer using analogies to Romeo and Juliet. Okay, the connection to TamIng of the Shrew maybe works, but still.) Honestly, Fifty Shades of Grey is better than this.
Aug 26, 2019 rated it really liked it
Better than 50 Shades of Grey. Plus, I want to read all of the plays now, so well done.
Xan West
Feb 24, 2017 marked it as do-not-read
Shelves: nope
Decided not to read because the author's note states "I dislike trigger warnings. But some people find them helpful..." & then goes on to give trigger warnings. This is not the book for me. I value trigger warnings, and I am not interested in a book that talks about them this way. This framing of them implies negative judgment about people who need trigger warnings--people like me.
I wasn't entirely sure going into this book what exactly it contained. I only knew from the blurb it was something of a memoir and something of an examination of sexuality in Shakespeare's plays. In reading it, it's definitely a mixture of both but I'm not sure if the melding of the two was such a good idea. Both ideas separately sound really interesting to me and focusing on them separately I feel like Jillian Keenan did a fairly good job. However in combining them it just wasn't cohesive and ...more
Feb 23, 2017 rated it did not like it
This review has been hidden because it contains spoilers. To view it, click here.
Zach Bramwell
Oct 04, 2017 rated it it was amazing
Overall, Sex with Shakespeare is as subversive and entertaining as the title. The unique blend of analysis and memoir make this book unlike anything I've previously read. Keenan has a complex story, as many within the Kink community do, that she tells within the realms of Shakespeare. I couldn't put this book down every time I picked it up. I would highly recommend this book to any sex-positive reader, regardless of Shakespeare background. Keenan's book is a work of genius that stands on its own ...more
Leandra Vane
Sep 17, 2016 rated it it was amazing
I loved reading this book for a cornucopia of reasons, perhaps most obvious being I share (and struggled with) the fetish she writes of so poignantly and I was also a literature major with a sweet spot for the enchantment and psychology of Shakespeare. This is a very well written memoir, a valuable piece to my sexuality collection, and I highly recommend it.

For more, read the post I wrote for this book on my blog The Unlaced Librarian:
Jan 02, 2017 added it
Shelves: memoir
"Pain suffers the same linguistic famine [as love]. There is the pain that empowers; pain that arouses; pain that frightens; pain that motivates; pain that discourages; pain that encourages; pain that recalls; pain that predicts; pain that breaks; pain that heals.... For all those pains, we have only one word." (pp. 194-195)

For me, this is one of the kernels of the book, which does its best to give words to that variety of experiences. I'm glad I read this.
Aug 10, 2016 rated it really liked it
Love of spanking, love of Shakespeare, love of a dude who doesn't love spanking and multiple sclerosis weave together into this compelling memoir that left me questioning how far I'd go for what I want.

Also, magical realism that I feel like shouldn't work but kinda does.
Amanda Kirk
Sep 04, 2016 rated it it was amazing
"What you blush to tell….is the most important part of the whole matter." Ars Amatoria

"If love be rough with you, be rough with love." Romeo & Juliet

Full disclosure: I checked this book out of the library because of its title. I figured, it could be awful but, with that title, I had to give it a chance.

It got off to a bad start: I was annoyed by the author's trigger warning -- until I read her snarky send-up of the concept.

The book starts, implausibly, in Oman, where the author is taking a
Rhiannon Root
Sep 09, 2018 rated it really liked it
Content warning: Sex, sexuality, fetishes, molestation, assault, drug use, health issues

Jillian Keenan’s “Sex with Shakespeare” is either going to be your exact cup of tea or it’s going to absolutely annoy the shit out of you. Fortunately, dear reader, you will know this either by just looking at the cover or by thumbing through the first few pages.

Keenan’s memoir opens during her time in Oman where she’s trying to conquer and fully get rid of her spanking fetish and her love of playwright
May 13, 2017 rated it really liked it
Shelves: non-fiction
A quick and entertaining read, Sex with Shakespeare is an informative examination of a serious subject - sex. In this memoir, Jillian Keenan shines a light on what it means to be a young woman with a developing sexuality, in this case a sexuality driven by a fetish for spanking. Keenan searches for clues to explain her desires, which she cannot openly discuss, especially in her teen and early adult years. In seeking to understand herself, she turns to Shakespeare whose plays and sonnets are ...more
Sep 27, 2018 rated it really liked it
This mixes modern Shakespearean interpretation with a memoir focusing on a woman’s journey in kink, so I’m all about it. This is a great read for people who are kinky, showing that you are not alone in your desires and seeing another person’s journey with it, and for people who are friends with or involved with someone who enjoys things that you may not, introducing you to it and well as allowing you to empathise. I think even without the Shakespeare mixed in, this would be a pretty great memoir ...more
Jan 10, 2020 rated it liked it  ·  review of another edition
Really more of a 2.5 for me, rounded up because a) the concept behind this book should earn Keenan credit, no matter how I felt about the execution; b) I liked her a lot as a person, and I was rooting for her; and c) her oftentimes literally naked honesty / willingness to lay herself bare was refreshing. But there were some issues for me, and the main one was that the 'conversations' didn't work for me, except in one or two very rare instances; I felt talked down to every time one appeared. I ...more
Aug 02, 2018 rated it liked it
Shelves: memoir, nonfiction
3.5 stars

When I took a Shakespeare class in college and we read "A Midsummer Night's Dream," I remember going, "ah, I would love to write an essay about kink and like-- whatever is happening here, between these characters," and then I didn't, but still, I had the desire to read someone reading into those dynamics in the same way I was. And so, here is "Sex with Shakespeare: Here's Much to Do with Pain, but More with Love," which is a memoir by a self-described spanking fetishist in dialogue with
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I'm a freelance writer based in New York. I've written for The New York Times, The New Yorker, The Washington Post, Slate, Foreign Policy, The American Prospect, Marie Claire, The Atlantic, National Geographic News, The Daily Beast, Al Jazeera America, Scientific American, Pacific Standard, Playboy, The Los Angeles Review
“I like to quote Shakespeare. But in this case, the rapper Eminem said it best: Words are a motherfucker.” 6 likes
“If I could mimic the dynamic of any Shakespearean marriage, I’d choose to mimic the Macbeths—before the murder, ruthless ambition, and torturous descents into madness and death, that is.” 1 likes
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