Im not reading all 20 pages but read the first few. Ill give you some prospective from the guys side.

One of my closest friends is a female and yes we did frick before but havent in years and never will again. We already are past that decision and made the decision we were never gonna be together and were better off friends. However most guys she dates dont care for me because of our closeness and their assumption that we have fricked and still do. Even though they are wrong in thinking we still do I can see how insecurity may set in so unlike this dude who seems a douche I dont try and make her boyfriends insecure by attention whoring for her attention. I leave her be so that guys can eventually realize my friendship with her is just that. A friendship and nothing more. And the time I spend with her becomes much fewer and far between than when we are single. And we both understand that but also know we are still best friends and cant have distance but still be there for one another. And it funny cause if ppl insinuate that oh yeah u want to be with her. My response is like no I definitely dont. I know way to much of the shite she does to have to ever deal with her as a gf.

So the whole point is yes your gf has more than likely fricked this dude before. And they have already made a decision not to be together and just be friends otherwise they would be together and you wouldnt be around. And if u or anyone ever asked her about being with that dude her response would likely be something to that similar to mine. Probably a yeah right u think I want a guy always flirting with every girl he sees etc...so honestly youre worrying about nothing pretty likely and I wouldnt worry at all. Sit back have a drink and present a confidence about yourself that as soon as yall leave youre going to frick the shite out of your girl and hes too much of a dbag to have anything to do about it.