Cindy Chupack got married for the first time when she was 25. Two years later, the man she married realized he was gay. They got a divorce. Chupack went on to have a successful career as an author and screenwriter, working on shows like Sex and the City. She won her first Emmy, and bought a house on the beach in California. Which made her second marriage, at 40, feel a little tricky.
For one, her husband, Ian, came into their relationship with a lot of debt — and was heading toward a not-so-lucrative career. "I was supportive of that...in theory," she laughs. But Chupack says that kvetching about her husband's spending habits isn't something she can do openly. "There’s no world in which women can [say], you know, my husband bought a Jeep he didn’t need...and some pot. There’s not really a great place to laugh about those things...without women kind of judging you."
As someone who’d spent much of her adulthood as a serial dater, she was also used to the autonomy of being able to dump someone she didn’t like. "I think I still had that empowerment when I went into the marriage, like, if this doesn’t work for me I am out of here," she tells me. But when Ian first brought up the possibility of leaving the relationship, it spooked her. It meant that she wasn’t totally in control. But, she says, “there’s life in my life now. It’s big and messy and out of control, but it’s what was missing.”