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I am a Licensed Clinical Social Worker with more than 20 years of experience working with adolescents and adults. I received my master’s degree in social work from Columbia University, and my practice is guided by the belief that life experience—our struggles, transitions, and personal growth—plays a vital role in helping clients navigate their own challenges. I bring both clinical expertise and grounded, real-world understanding to the therapeutic relationship.
My passion is helping people navigate anxiety, depression, and life transitions across the lifespan. I support those facing challenges in young adulthood, work stress, self-confidence struggles, impostor syndrome, relationship and family conflict, parenting, retirement, and the search for meaning at every stage of life. Don't hesitate to reach out with any questions!
Jessica Massaro, LCSWR (New York licensed), owner of Compassionate Connections Sex & Couples Counseling, PLLC, is a kink & fetish affirming relationship therapist and her goal is to help folx within (mono or ENM) relationships address concerns with their communication, create intimacy and connection, reignite chemistry, and provide sex education, because you CAN have the pleasure-filled life you're seeking. Jessica also works comfortably around issues of infidelity repair.
Have you struggled to find peace of mind in life? Have life's transitions thrown you for a loop? Sounds like you've been trying to get the most out of life and that journey has impacted your mental health. This is where I can join you, right where you are, with whatever concern(s) you have. I work with adults and teenagers to find the balance they've been looking for.
I believe in everyone’s inner strength and ability to self-actualize and achieve their goals given the appropriate tools and support. Therapy is a tool that can help you start your journey in achieving the life you desire. I have 7 years of clinical experience as a social worker. I graduated from Columbia University with a master’s degree in social work and have worked in various settings including hospitals, schools, and universities.


Headway makes it easy to find support for your mental health — from finding the right provider, to understanding costs, to scheduling with ease.