Sissy: Jacob Tobia


Jacob Tobia’s Sissy: A Coming-of-Gender Story is a hilarious and honest memoir about the realities of growing up gender nonconforming.

Sissy: A Coming-of-Gender Story, Jacob Tobia

Jacob was born a male – they had all the “right” male parts, an older brother to guide them into boyhood, society baring down on them with the image and expectations of what a boy or a man should be and look like. And yet, they wanted to wear tutus during dress up in kindergarten, wanted to have sleepover with girls, and wanted to play with Barbies.

These desires were allowed to an extend, until Jacob grew and it became obvious that they did not fit the prescribed mold for a boy. They quickly learned that conforming to a gender stereotype was easier than sticking out, than being mercilessly bullied by their brother and his friends, than being ostracized.

As Jacob became a teenager and spent more time thinking about their identity, they came to the conclusion that they were gay. Jacob came out to their friends and family and thought it was all over – that they were done coming out, done exploring their gender identity. In the years to come, however, Jacob would find that “coming out” happened more often, and far less dramatically, than their first.

Through college and post-grad, they were able to fully explore their gender identity, understand that gender fluid, nonconforming, and queer were all accurate descriptions of their identity. Jacob beautifully details the times in their life when it was devastating, surprisingly easy, and even joyful to be gender nonconforming and how they came to own their identity with pride, bright red lipstick, and 5″ stilettos.

Note: As you can see, Tobia’s preferred pronouns are “they/them.”

Content Warning

Please take caution while reading Sissy if any of the following topics may trigger you:

  • Suicidal thoughts
  • Death or dying
  • Transphobia and homophobia

My Thoughts

Why are you still sitting there reading this blog post?! You must go to your nearest independent bookstore and BUY! THIS! BOOK! Seriously, this should be required reading. Tobia so generously and delightfully tells the world of their gender identity – one that is often left out of the trans narrative – and we should all soak up every last drop of it up.

Besides the utter importance of the message and representation that Tobia is gifting to the world, what makes this book great is the wonderful writing. You’ll feel like their best friend – you’ll laugh and cry and get angry with them like you were there for the experiences that have shaped them as a gender nonconforming member of our oftentimes harsh society. Tobia strikes a unique balance between vividity of painful moments and an almost constant lightness that sucks you in to the memories and leaves you constantly wanting more of their storytelling.

Sissy takes us through Tobia’s life and the evolution of their gender identity, from effeminate toddler to gay teenager to ultimately, and still evolving, trans adult. Tobia is an extremely accomplished twenty-something, and they recount many of their successes throughout the book – Sissy is basically the most fabulous humble-brag of all time. This integral to the story because it shows the reality that no matter how successful they are, no matter how many awards and accolades and scholarships they receive, they are still marginalized because they don’t prescribe closely enough to one of the two constricting gender identities society is comfortable with.

All of this to say, Sissy: A Coming-of-Gender Story touched my heart, made me laugh, taught me so much, and made me think. What more could you ask for in a book? I highly recommend this memoir, especially if you like yours peppered with humor and depth.

Thank you so much for taking the time to read my thoughts on Sissy: A Coming-of-Gender Story. I’d love to hear your thoughts on the memoir in the comments or at my Instagram, @bookmarkedbya!

4 Replies to “Sissy: Jacob Tobia”

  1. You’re spot on about how Tobia feels like a friend while reading! (They’re even my celebrity crush now, lol ❤ ) I felt bad for them when an interviewer they had a crush on asked if it's offensive that they do some of the things they like to do, like wearing heels, since those things can be considered "stereotypically" feminine in our society.

    I thought about this for a bit today, and my conclusion is that it's still okay for there to be patterns in a culture that people in that culture will tend to associate with femininity, or masculinity, as long as no one pressures anyone to do those things, or not to do those things if the person wants to, or invalidates the person's identity because they do or don't do any of these things. I believe Tobia's talks are about how heels, lipstick, etc make *them* feel feminine, not that anyone who identifies as female and/or feminine *has* to do things like these.

    (I'm sure I'm preaching to the choir here lol, just so excited about this book and to see a review on WordPress)


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