I have been in a long-distance relationship with my girlfriend for two years and we have finally begun to have conversations about our future. Until now, we just accepted that we were okay with this arrangement but it is clear that we have to take a stand on what to do next because we are unsure if this will work. We know that if we aren’t together in the same city, this relationship will fail because we are already drifting apart and neither of us wants that to happen. I want her to be with me, but I am still worried about the impact on our individual careers and how long it will take for this move. Part of me is considering letting her go so she can get on with her life while I figure out my next step. What should we do?
When you say there are conversations about the future, do either of you discuss your feelings and how important you are to the other person? That is pretty much the crux of the issue because if separating is a convenient option, it implies that you are both okay with not being in this relationship. If that is true, being in the same city only hastens the inevitable. Why not talk about what you both want from the other person, and whether you are both okay with letting the other go. If this is mutual, it should be easier for you to figure out if any sacrifice is worth it to be together.

My best friend and I had a bet to ask a girl out, even though we didn’t like her, and she accepted both our requests. We don’t know what to do because if we cancel she will be insulted. How do we get out of this?
You and your best friend should re-evaluate how you spend your time and think about what it means to treat people like commodities. I suggest you both speak to this girl, admit the truth, and apologise.