Before I get into anything I am going to give a bit of back story on this girl. I have known this girl for nine years and she is best friends with my brother and is good friends with two of my best friends. We have hung out a lot in the past nine years and have talked a lot in the past nine years. In those past nine years I have hung out with her at my house, her house, friends house, gone to parties etc. etc. For the past month or two her and I have been getting to know each other, we text a lot and skype a lot (she goes to a different college so we cant see each other face to face). We have even driven down to see each other a few times. Now, my Thanksgiving break started on friday, as did hers, so I hung out with her and her friends on Friday, took her on a date on Saturday, and hung out with her and her friends yesterday. But, here comes a problem. I have absolutely no idea what her dating history is. I don't know if she has ever had a boyfriend, I have no idea if she has had sex let alone kissed a guy, and, quite honestly, I can't even take an educated guess. So, my question to you is, at what date is it appropriate to ask a girl about her history? Thanks in advance for all those that read and helped.