Babe in Boyland by Jody Gehrman

Summary from Goodreads

     When high school junior Natalie--or Dr. Aphrodite, as she calls herself when writing the relationship column for her school paper--is accused of knowing nothing about guys and giving girls bad relationship advice, she decides to investigate what guys really think and want.

     But the guys in her class won't give her straight or serious answers. The only solution? Disguising herself as a guy and spending a week at Underwood Academy, the private all-boy boarding school in town. There she learns a lot about guys and girls in ways she never expected--especially when she falls for her dreamy roommate, Emilio. How can she show him she likes him without blowing her cover?

      There were many aspects of BABE IN BOYLAND that were a bit strange, but they all helped to make this book even more fantastic. The plot of Natalie going undercover at the all-boy school reminds me of the movie, She's the Man. They are both filled with funny, complex characters and kept me laughing for hours. Natalie is confident and sure of herself despite her limited dating history. She is hardly hesitant about the plan and determined and spontaneous. She loves her best friends, Chloe and Darcy, so much and they are a huge part of Natalie. They continuously help her during her time at Underwood and contribute lots of hilarious commentary. Emilio is a walking contradiction. He is suave and has confident swagger, but blushes when he receives compliments. He is cautious of friendship and feels as if he doesn't fit in anywhere, but gradually reveals important parts of himself to Natalie. I think this makes for a great start to their relationship, that he told her that with no pretenses, whereas if she where acting as a girl, he would've been less likely to reveal his feelings.
     I felt like I was experiencing the gender change with Natalie. Her descriptions were detailed and funny. Sometimes I wonder how nobody was suspect in the first place because most of the stuff she said always sounded girly to me. I realized how hard it must have been to do what she did because trying to stop being a girl would be like suddenly trying to turn into a block of cheese. She made me also realize the intense differences between guys and girls and why they go so perfectly together. She also showed me that gender isn't mostly factored around how you look on the outside, but how you act. Natalie definitely won a Grammy in my eyes after stepping into this strenuous role of boy. She deserves much kudos for her efforts and resisting insanity as she witnessed butt-flossing and sacrificed herself for my gender. Her tips and knowledge will be not be forgotten and surely put to use in my dating future.