This is not an easy question to answer, however, I honestly would probably be okay with it... depending on the amount of time she would want to spend in "guy" mode. Before you start yelling hipocrite at your computer screen... I fully understand that when a girl starts dating me she is expecting to have a "boy"friend, and I think I deliver the goods on that one. Crossdressing defines me to a certain extent to be sure, but my world does not revolve around it. So basically if it was something she "liked to do from time to time" because she feels compeled to "express that side of herself" freaking bully for her! That is pretty much how I define my crossdressing. I use that scenerio because honestly I don't really think any other one is plausible because while I do have a soft spot for "tom boys" mainly I prefer closer to the girly-girl side of the spectrum.