Jesse's Girl

Boss Ladies

In this episode, I interview a few of the ladies I go out to dinner with. It’s a group that’s formed over the years, each woman was brought in by another. Our bond is one part wine, one part good food, and two parts great conversation. I’ve been told it’s hard to make friends, REAL friends, after the age of 30. I’m grateful I didn’t have that problem. These women are smart, successful, struggling, supportive, and sassy. I’ve known them for years now and even I was surprised by some of their answers to my questions.

Jesse's Girl

In this episode, I interview a woman who busted a glass ceiling for me. Like me, she was not from Brookline originally, like me, she was young and energetic and the best kind of nerdy. She won Townwide office at the age of 25 and two years later served as a Select Board Member for nearly six years. Although we never overlapped, our paths were eerily similar. As my own political path comes to its close, I wanted the opportunity to chat with this trailblazer.

Horse Crazy

In this episode, I interview a few of the barn girls where I keep my horse, Raisin. These girls are between the ages of 14 and 19 and are some of the toughest, sweetest, smartest, and most hard working girls I know. They astound me with their maturity, their tenacity, and most of all, their ability to command respect from large animals, but I am also heartbroken to hear their stories about body shaming, cyber bullying, and immature boys.

Transit Queen

In this episode, I interview my friend Constance. Who was assigned the wrong gender. It would take her decades to come to terms with her true identity and to embrace that person. I knew her as John, once upon a time, when we worked together in the transportation sector. A few years ago, we bumped into her and met her as Constance and I’m privileged to call her my friend. She is a transit nerd, an animal lover, and an inspiring smart girl. She shares what it was like coming to terms with living a double life, the fall out of coming out, and what it feels like now to be your authentic self. Content warning: suicide