I'm a male-to-female and I liked "Transamerica" even though it was not at all relatible to my own life. I was always feminine - was teased, called a little girl, sissy...and much worse, in junior high and high school - and started the transition in my late teens. That may have been what your friend was talking about when she said she found it 'offensive.' Bree made the transition later in life after fathering a child, and especially when you factor in Bree always wearing stereotypical girl pink and purples, then her claiming to be a Christian: fitting all the traditional stereotypes of what women are supposedly "supposed to be."
Actually, this movie reminded me a bit of the Renee Richards story, "Second Serve." A middle-aged male making the transition to female after a brief marriage where he fathered a son. Renee Richards also speaks in the same low, monotone voice, which did make me wonder if the Bree character wasn't slightly modeled after Renee, and perhaps a few other real-life transsexuals.
"I'm Chickie! Fly Me to Quaalude!"
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