Therapists
Olivia Jessar, LMSW
(SHE/HER)
Associate Therapist, Licensed in NY
Olivia sees clients in person and virtually
Past experiences and difficult relationships can leave us carrying shame, feeling emotionally disconnected, and unsure how to trust ourselves or others. You may find yourself constantly overextending, struggling to set boundaries that last, or losing sight of who you truly are. If relationships feel exhausting, saying “no” seems impossible, or your sense of self feels foggy, you’re not alone. These experiences have roots, and together we can explore and help transform them.
I offer trauma-informed therapy for women and LGBTQ+ individuals looking to heal from relational wounds, family dynamics, and identity-related challenges. As a queer therapist, I understand how self-discovery can be nonlinear, and that the hardest part of growth isn’t always insight, but learning how to live differently and in alignment with your most authentic self.
In our sessions, I blend psychodynamic therapy and person-centered approaches with warmth, honesty, and compassion. I create a nonjudgmental space where you can speak freely, without self-censorship or worry about being “right” or “wrong.” You’ll be invited to show up fully and authentically as we build deeper self-awareness and explore new ways of relating to yourself and others.
My approach is grounded in feminist and anti-racist values, with an understanding of how systemic oppression and cultural messaging can shape our internal narratives. You are already worthy and valuable – therapy is simply a space to reconnect with that truth and learn how to move through life with more clarity and self-trust.
Together, we’ll work toward meaningful, sustainable change – whether that means setting healthier boundaries, healing from trauma, reducing anxiety, or cultivating a stronger sense of self. You are the expert of your experience; I’m here to support your growth, insight, and transformation.
When I’m not in session, you’ll often find me relaxing in the park, wandering through the city, or sweating it out in a hot yoga class.
Q & A
1.How would you describe your therapy style?
My therapy style is relational and collaborative! It may sound corny, but I like to think of it like we’re hiking through the woods together – you’re the one leading the way on your own path, and I’m right there beside you as your guide and companion. You decide which direction feels right and what matters most to you, while I’m there to offer support and gentle guidance along the way. I believe you already have the wisdom and answers inside you, and my job is to help you tap into what you already intuitively know deep down.
2. Have you been in therapy yourself?
Yes, I’ve absolutely been in therapy myself! Actually, being in therapy is what inspired me to become a therapist. I worked with my therapist for five years, and the relationship we built together was deeply transformative for me. The experience of feeling truly seen, heard, and deeply understood by another person was incredibly healing. This is what I believe everyone deserves to find in therapy, and my own experience as a client really shapes how I show up for each person I work with. It reminds me what it feels like to be on the other side of the couch and helps me create that same kind of safe, understanding space for my clients.
3. What books have made the biggest impact on your life?
My Brilliant Friend
This is such a beautiful novel about a complex friendship between two young girls, following them into adulthood. The author touches on themes of class and access to education, sexism and growing up and living in a patriarchal society, and what we share with our loved ones versus what we keep hidden. I just loved reading about the beautiful and complicated relationship between the two women, and how important they are in each other’s lives.
The Parable of the Sower
This novel is a classic and is so relevant to our world in 2025 – I mean it was written in 1993 but set in the year 2025! It’s set in a post-apocalyptic America that has been decimated by climate change and social inequity. The book is both terrifyingly real but also oddly comforting because community and solidarity are central themes throughout.
The Gift of Therapy
I love this book because it offers really raw insights from a clinician’s decades of experience and shows us what really happens in the therapy room. The author highlights how genuine presence and vulnerability between therapist and client can really be more powerful than any specific technique or theoretical framework – which is what I believe as well! I truly recommend this book for both therapists and clients!
