My friend's brother is a year older than I and we have had (let's just say) a romantic past where our feelings were made known to each other. We have known each other for a long time, we get along really well, and we have a lot in common. However, at this point, probably the only thing keeping us from acting on our feelings is his sister and my friend, who disapproves of us dating. Relative to siblings, they are very close, she doesn't think we are very compatible, and she doesn't want him to, essentially from her explanation, take me away from her. I can see where she might concern herself with these things, but I also think they're invalid and selfish of her. If I were in this situation, I like to think I wouldn't hesitate to let her pursue what makes her happy. However I realize still trying to date her brother would make me pretty selfish too. That in mind, I still think happiness is worth trying to find even if it's unlikely for everything to work out perfectly or even work out at all. What about you guys?
Most Helpful Girl
Generally speaking, if a friend told me this, I would say it is a bad idea on principle because if things go south with the brother, it will be hard to avoid your ex if his sister is your friend. It will make things incredibly awkward all round, and may even put your friend in the difficult position of having to choose sides. That is... if you still have her as a friend to begin with. It sounds like she is against this relationship. If you choose to go ahead with it, she may take it as a sign that you value her brother more than you value her. It sounds unfair but I'm trying to be realistic about human feelings and reactions. I've seen this happen too many times.
Of course, the decision to date her brother still remains with you. You just have to ask yourself if it is worth potentially sacrificing the relationship with your friend. In an ideal world, you will remain good friends with the sister while happily dating the brother. But when stakes are high, you need to make your decision based on the worst case scenario, not the best case scenario. And so, keeping in mind that there is a chance that your friendship with the sister will become awkward or ruined for a variety of reasons, and even more so if the relationship with the brother doesn't work out, are you still willing to risk dating this guy?
If you are prepared for possible consequences, then go for it. My father married my mother, who was his best friend's sister, so occasionally, it all works out. I would just proceed with caution because in most other cases I've seen, it tends to end in disaster at some point.1