'Nothing prepared me for this': What it's like to be part of Caitlyn Jenner's TV entourage

Author, academic, activist: There was nothing in Jennifer Finney Boylan's resumé to suggest she'd someday find herself on a road trip with a refugee from Keeping Up With the Kardashians.

But that's exactly where Boylan, who grew up in Newtown Square and Devon and graduated from the all-boys Haverford School, can be found Sunday. On the E! docu-series I Am Cait, which returns for its second season at 10 p.m., Boylan travels the country as one of the transwomen Caitlyn Jenner refers to as "my girls."

"Nothing in my life prepared me for this," Boylan said in an interview in January.

"I never thought I would be on the show. In fact, I wasn't supposed to be on the show. Season 1, I was going to be a consultant. Because I'm the cochair of the board of directors of GLAAD. I was there to tell them: 'Don't do this. Do do this.' . . . They dragged me on camera one day, and the next day, and the next thing I know, I'm up here," she said.

"It may help to be an English teacher, someone used to talking about issues," said Boylan, a Barnard College professor whose books include the 2003 memoir She's Not There: A Life in Two Genders.

In Sunday's episode, it's Boylan who leads the charge against Jenner's conviction that there's no disconnect between her conservative Republican politics and support for transgender rights.

Boylan also presses a reluctant Jenner to talk about her sexuality.

"Maybe that was unfair," Boylan said, "but on the other hand, she's in the process of figuring out who she is. This is one of the questions that she's going to have to start thinking about."

Though she divides her time among New York, California, and Maine, where she lives with her wife, whom she married before her transition, and their two sons, Boylan said she misses Philadelphia.

In December 2010, while teaching for a semester at Ursinus College, she spoke at the Haverford School, from which she'd graduated - as James Boylan - in 1976.

"I was shocked. Here's this all-boys school [with] a reputation for being somewhat conservative, and the boys gave me a standing ovation. They welcomed me with open arms," she said.

"It was like the dream you wake up from. You're back at your high school, except that you've changed genders. But, in fact, there I was. It was one of the most powerful experiences of my life. And I was so proud of that school."

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