Question:This question is for my friend's situation: A boy recently started to pursue more-than-friends moves on my friend. She's liked him on-and-off for three years, but in those three years he's had a girlfriend. She just found out that the boy had sex a few times several months ago with his girlfriend. Since that time they broke up. My friend's hurt and trying to look past his past. She feels that everything she will do physically with this boy won't be special since he's already went all the way. (She's never had a boyfriend before.) She really likes him. They are both Christians. Should she go out with him once he repents and they strive to control themselves?
While you label both the boy and the girl "Christians" neither one is behaving as Christians ought.
He has used his past girlfriend for sex and notice that it did nothing for the stability of the relationship. You indicate that he has no regrets regarding what he did since he has yet to repent of his sins, even though it happened months ago. "For godly sorrow produces repentance leading to salvation, not to be regretted; but the sorrow of the world produces death" (II Corinthians 7:10). Though your friend has known him for three years, I take it that they've only been dating since his break-up a short while ago. Despite the newness of this relationship, he is already trying to get her pants off. Now, honestly, does this strike you as a boy who wants to be a Christian or who has some desire to repent for his sins?
Your friend isn't much better. It isn't that she is appalled that he used his past girlfriend for his own pleasure. She's annoyed that she won't be his first. In other words, you are telling me that she already plans to have sex with this boy she just started dating. Worse, she wants to pretend that his sexual exploits didn't happen because she wants to "look past his past" when he hasn't left his past.
Both need to see things as they are, not as they imagine them to be. Both are involved in sin. That needs to be rectified first -- from the heart. "For observe this very thing, that you sorrowed in a godly manner: What diligence it produced in you, what clearing of yourselves, what indignation, what fear, what vehement desire, what zeal, what vindication! In all things you proved yourselves to be clear in this matter" (II Corinthians 7:11). When each has control over his or her personal desires, then if interest remains they can talk about possibly dating where they both respect the other person and want the best for that person. Right now, each is focused on what he or she personally wants.
People do change. But before making a commitment, make sure the change has taken place first. Don't gamble that it might take place later.