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Both Sides Now: One Man's Journey Through Womanhood

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A man who underwent gender reassignment recounts his painful early efforts to accept the female body he was born with, his experiences with living as both a woman and a man, and his discovery about the spiritual and political ramifications of his life. 15,000 first printing.

336 pages, Hardcover

First published January 1, 2006

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Dhillon Khosla

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5 stars
27 (25%)
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37 (35%)
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31 (29%)
2 stars
7 (6%)
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Displaying 1 - 15 of 15 reviews
Profile Image for liz.
276 reviews30 followers
May 7, 2007
So it looks like I'm entering into a fiction backlash (or at least literature?). I'm in the middle of Barbara Ehrenreich's latest, and I finished this one over the weekend. It's about a woman (at least at the beginning) who spent the first few years of her life in Europe, is now living in San Francisco as a lesbian, but still feels like she isn't fully herself... So begins her odyssey of entering into a transformation from a woman to a man, the process of aligning her physical state with where she's been mentally throughout her entire life. I liked his almost-painful honesty about all of the changes he went through, and how it made him feel at each step of the way. Chapters go by month, and each chapter begins with recounting a dream he had at that time. It's a little bit gimmicky, but good because it indicates how integral a part of his identity being a man is/was, even when he was a she. The writing isn't too novelly, which I needed, but it's still an intriguing story that moves along well. It's nice to know that, as much as I don't like some things about being a woman, I definitely don't want to be a man -- I've never felt the same sense of despair or misalignment as he did. Here's a decently representative quote:

After the meditation was over, and before our group exercises were about to begin, we had a short break. I headed in the direction of the bathrooms, feeling a growing sense of trepidation as I neared the two doors. There was no third door--no place for those of us suspended in between. And there was no way I could go into the women's room without feeling the first few fragile signs of my manhood erased.

The book covers July 1997-November 1999; the above quote comes from February 1998. While the book never has the take-a-step-back introspection of, say, Joan Didion, that's not what he's going for. It's much more about immersion, taking the reader along for the ride.
113 reviews2 followers
July 18, 2016
Very interesting. Especially the type of phalloplasty he describes receiving in the late 1990's, as this technique is not widespread today and the inferior methods that he rejects are still commonly practiced. After reading about transition and speaking with transgender individuals for many years, I didn't know that type of phalloplasty was possible. His description of metoidioplasty and his complications were interesting as well because anecdotes are always fascinating and knowing that complications are possible is just not the same as hearing a personal story about experiencing them.

It was very moving to read about his interactions with his parents and the description of his father's acceptance and his realizations about his mother. It was also very sweet to read about his interactions with various women in his life and amazing to learn about the incredible doctors, nurses, and other healthcare professionals he encountered on his journey.

This is a story about a very interesting and introspective person. It's pretty cool to be with him for only this one part of his life. It's a little like watching a television show that covers only a couple years of a fascinating character's life. I can identify with his spiritual searching and I share his habit of recording dreams. I'd read more biographical work from this author that had nothing to do with transition because he's an interesting guy and witty writer.
27 reviews4 followers
October 13, 2010
This is a terrifically interesting autobiography. Dhillon, the author, documents his transition from the wrong body (female) to the right one (male), but there is far more here than this journey. Dhillon gives us much anecdotal information in the form of flashbacks about his life before transitioning, revealing the 'clues' there had been in his early life and the reactions he had to the things in his life which were incongruous with his real gender identity. It's also a story of immense interest and depth of the life of a man.

I'd love for this to be compulsory reading in schools, except my own experience tells me that 'compulsory' reads lead you to loathe the texts concerned (I still cannot bear Lord of the Flies, for example, and where I would have loved Animal Farm if I had found it for myself the joy of it was lost on me when I was required to analyse it cover to cover).

Anyone who has questions about their own gender or who is contemplating transitioning would find this book a fascinating revelation and likely learn immensely from it. Too, though, women who have always wondered what it is like being a man would find this book equally revealing. Dhillon writes beautifully and I am very grateful for his sharing his experiences with his readers. Please do read it!
Profile Image for Jack.
Author 4 books22 followers
December 23, 2007
i don't know. this is not a bad book, but i have to say that i came away a little more well informed, but less likely to want to meet this guy. i felt him get a little transier-than-thou quite a bit, but there's not much you can say as a reader when it's a book about his life, his experience, his worldview. it's hard, with tell-all memoirs, so separate the writer from his work, and i'm not sure it should be a requirement.

i'm reading Testosterone Files at the same time, and just find Valerio more engaging, a better writer, and really, just more open hearted and willing to examine himself and the world around him.

so, given that logic, does someone have to be a good writer to write a good memoir? i think so. i think i preference good writers over good people.

Profile Image for Née.
172 reviews11 followers
January 21, 2011
Picked this up cause it was on sale at Chapters and didn't know if I'd like it or not. I was actually surprised by how great Dhillon's writing was. Simplistic yet very, very good at describing what he went through during this whole journey. There are some parts of the story that may be difficult for some to read (graphic and/or painful) but I think it's definitely a book worth reading. Fascinating.
Profile Image for Luka.
8 reviews
June 18, 2011
First book I ever read on the subject of transexualism in 2006/2007. It resonated deeply with me. Dhillon obviously in a position to afford pioneering lower surgeries. A likable man, with a strong spiritual soul and romantic at heart. I enjoyed his insight and felt like I was a part of his journey, there for the highs and the inevitable lows of transition. Dhillon displays dignity throughout and his quest to become complete.
Profile Image for Annie Feng.
186 reviews30 followers
December 14, 2013
Oh. My. F. I found this book.

One of the most heartfelt and enlightening biographies I've ever read. It's simply...no. It's not simply anything. It's that awesome blend between educational, fun, teary, and struggles of a strong individual. It's beautifully written, though not as well known as some of the other biographies (took me a LONG time to find it), it's a life changer no matter what sex/gender/sexuality you define with.

Profile Image for Jesse.
769 reviews8 followers
March 3, 2008
Another trans narrative. I just really didn't like this guy's sexism, sizism, internalized transphobia and general cockiness and generalizations about men and women. Well described process of a medical transition but this is the sort of guy I wouldn't want to get to know.
Profile Image for Sarah.
49 reviews3 followers
November 7, 2007
Well written. I just got annoyed by the author's personality.
7 reviews2 followers
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August 13, 2008
I love books about spiritual journeys!
Profile Image for Florence Buchholz .
955 reviews24 followers
November 14, 2008
I can't imagine wanting something so much as to be willing to go through such physical and mental anguish.
Profile Image for Deborah.
12 reviews1 follower
March 26, 2009
Very interesting book. Was very compelling, was one of those books that you did not want to put it down.
794 reviews6 followers
February 23, 2010
Further educated me about transgender issues. Mind-boggling emotions, heart breaking details. Lots of clinical and explanatory information I hadn't read in more emotional narratives.
116 reviews2 followers
July 5, 2009
Autobiography of female to male transexual.
Displaying 1 - 15 of 15 reviews

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