It's a Boy Girl Thing (2006)

Director: Nick Hurran

Cast: Samaire Armstrong as Nell Bedworth, Kevin Zegers as Woody Deane, Sherry Miller as Katherine Bedworth, Robert Joy as Ted Bedworth, Sharon Osbourne as Della Deane, Maury Chaykin as Stan Deane, Mpho Koaho as Horse, Dan Warry-Smith as Team Guy #1, Balázs Koós as Glixen (as Balazs Koos), Emily Hampshire as Chanel, Brooke D'Orsay as Breanna, Kathryn Haggis as Miss Bidermeyer, Genelle Williams as Tiffany, Alex Nussbaum as Mr. Zbornak, Jack Duffy as Old Man

This movie was actually really good Kevin Zegers done a great he was
really believable you could really see the difference from when he was
a guy and when he was the girl and Samaire Armstrong was amazing also
loved the man walk. It was kind of typical story line, a mix of Hot
Chick and Freaky Friday I'd say,nothing new, what makes this movie
stand from others is the chemistry they had on screen, they worked well
together which made the movie so much better. The only think I disliked
was the fact that Sharon Osbourne was the mother, she seems like a
great person, but I don't think she's a great actor some scenes made me
cringe, they should have cast someone else. But overall I was
impressed.