I have known this guy since middle school and have always had feelings for him. Over the summer he recently told me he had had feeling for me for quite some time also. I am senior in high school and he is a freshman in college. He recently told me he had sex with some girl while at college. He blames it on being really drunk, which obviously is not an excuse, and said he didn't even enjoy it. Regardless it still happened. My question is whether or not I should give this guy another chance. I know I am going to wait until marriage to have sex. Also if I do give him another chance and it works out, would it be wrong that I'd be a virgin and he wasn't when we have sex once we're married?
Sins do happen. The better question is: Is he going to change and do you see evidence of it? There are several problems that are arising. The first is that he is getting drunk. Drunkenness is just as much a sin as his fornication. "Do you not know that the unrighteous will not inherit the kingdom of God? Do not be deceived. Neither fornicators, nor idolaters, nor adulterers, nor homosexuals, nor sodomites, nor thieves, nor covetous, nor drunkards, nor revilers, nor extortioners will inherit the kingdom of God" (I Corinthians 6:9-10). Sins are not permanent and people can change. But what this means is that you have to watch and see if he continues to drink or if there are other signs of him lacking self-control.
A marriage to a non-virgin is not wrong. You need to see a man for who he is and not who he used to be.