Has anyone ever dated their best friends sister and started feeling really guilty and depressed about it? My best friends sister and I have started seeing each other and I get along with her really good, I don t know her that well, but I really like her. My friends girlfriend is not at all ok with me dating her, she says that I am like a brother to her and it fels really awkward because her and buddys sister are best friends. She is now telling me that she feels so awkward about it all the time that she is going to break up with my buddy. I am also business partners with my buddy and I am starting to not like the whole situation. Buddy says that he Doesn t care what we do and it is up to us. He isn't the type of person to be angery and usually gets over stuff, but if his girlfriend leaves because of this it might be different. Do you have any advise?