Jesse James Rose in Conversation with Matt Rodrigues

We are thrilled to hose Jesse Jame Rose for an evening at Three Avenues Bookshop, where she'll be in conversation with Matt Rodrigues to discuss and celebrate her memoir: . The event will feature a conversation and audience Q&A moderated by Matt Rordrigues. An author meet & greet and book signing will follow.

When: Wednesday, October 22nd at 6:30 pm (doors open at 6:15 pm)

Where: Three Avenues Bookshop - 3009 N Southport Ave, Chicago, IL 60657

Copies of will be available for purchase during the event. Participants will have the opportunity to get their copy signed by Jesse James Rose!

A powerful, provocative, and genre-bending literary memoir that grapples with victimhood, recovery, and resilience
In the before, Jesse James Rose is happy. She has a beautiful boyfriend with melty glacier eyes, she’s on a euphoric journey of gender exploration, and New York City is perfect.
In the after, she’s single, making dinner for her grandfather, and wondering if he’s going to forget her name today. Except, in the before, her first-grade music teacher led her into a dark room to show her something he shouldn’t have. And in the after, she’s finding healing and comfort in coming into her own, even as her grandfather declines.
In the before, she was fine, more or less. But in the after, she has to reckon with whatever the hell restorative justice really, truly means.
Following the aftermath of an assault, and the heartache of caring for a grandfather with Alzheimer’s, sorry i keep crying during sex tells a captivating story of identity, recovery, grief, survivorship, and transness. Through lists, theatrical scripts, flashbacks, and Grindr DMs, Jesse James Rose’s genre-defying memoir is raw and hysterically funny, and takes readers on the wild ride of overcoming the struggles of a trans twentysomething.

Jesse James Rose (she/they) is a transgender actor, writer, and content creator based in New York City. Every president who has attacked her in the media has been shot at. Rose holds degrees from NYU in music theatre and child and adolescent mental health studies, as well as a certificate in diversity, equity, and inclusion from Cornell University. As an actress, Rose made queer theater history as the youngest openly nonbinary professional performer to take on the title role in Hedwig and the Angry Inch. The same year they co-starred in the indie film Adelphe, which premiered at the Cannes Film Festival. They are perhaps most known as a transgender activist attacked by Donald Trump, as covered by Rolling Stone and THEM. Their work lives largely on social media, where Rose writes about gender, queerness, survivorship, mental health, their feelings, and their exes on Instagram & TikTok (@jamesissmiling).

Matt Rodrigues (he/him) is the Emmy-winning host and executive producer of NBC Chicago’s top-rated daily lifestyle show Chicago Today, as well as the uplifting A.M. series Matt in the Morning. Known for his infectious energy and genuine curiosity, Matt brings viewers the most inspiring stories and unforgettable adventures from across Chicagoland. As part of the NBC family he’s also a regular contributor on The Today Show and The Kelly Clarkson Show.

In 2023, he created, hosted, and executive produced the two-time GLAAD Award-nominated Peacock series It’s Ok to Ask Questions—a bold and acclaimed interview series featuring unfiltered conversations with LGBTQIA+ trailblazers, where no subject is off limits. 

Prior to his work in Chicago, Matt hosted and produced for POPSUGAR, including their nationally syndicated entertainment show POPSUGAR Now, Oscar red carpet coverage and the Hilton Hotels branded travel series, Find Your Happy.

Three Avenues Bookshop's goal is to be a safe, accessible, and inclusive space for all. Please email us at [email protected] to let us know if you need any accommodations for this event, and we'll do our best to meet them. Accommodations can include but are not limited to the following: space for a wheelchair or other mobility device, masks, answering questions about the space over the phone or email ahead of time, etc.

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