40 Plus: Gay Men. Gay Talk.

Taking PRIDE in our Mental Health – Will Dempsey


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Pride season is supposed to be all glitter, joy, and celebration—but for many, it can bring up waves of anxiety, loneliness, and even depression. So how do you keep your spirit lifted when everyone else seems to be riding rainbows, and you’re just trying to stay afloat?

In this powerful and heart-centered episode, we’re joined by the fabulous Will Dempsey—licensed social worker, drag queen, and fierce queer mental health advocate from Heads Held High Counseling. Together, we explore how to protect your peace and prioritize your mental health during Pride and beyond.

Will dives into:
• How to climb out of the emotional rabbit hole when anxiety and depression pull you down
• The importance of connection and chosen family in healing and self-discovery
• Ways to activate your pride—not just as a celebration, but as a tool for transformation

Whether Pride fills you with sparkle or feels a little heavy this year, this episode is your permission slip to feel it all, find your people, and lift your head high.

About Will
Will Dempsey is a social worker, drag queen and queer rights advocate. He is the founder of Heads Held High Counseling, a LGBTQIA+ virtual group therapy practice supporting queer and trans individuals across Massachusetts and Illinois.
Will's innovative approach to social work seamlessly blends his creative flair with his commitment to advocacy, making mental health care both accessible and affirming for marginalized communities.
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