The anguish you feel about two of your friends breaking up might be close to the pain the couple is feeling themselves, especially if you are very close to the both of them. Often, a line is drawn in the sand and friends are asked to choose a side, putting the burden on you. However, you may not want to pick one friend over the other, especially if you met them both at the same time. Even if you knew one before the other, San Diego life coach Dana Miller suggests being honest with both parties and setting ground rules to ensure that everyone is okay with the situation.
State your position. If you feel strongly about your friendship for both people in the relationship, make it clear from the start that you are not taking sides and that you want to remain friends with them both, separately. Allow each of them to decide if that is something they can handle.
Don't talk about the ex when hanging out with one of them. No one wants to hear about his ex every time he hangs out with mutual friends. Talk about everything but the ex. If you happen to mention a trip you're taking with friends, it's okay to say the ex is coming along, but it's not necessary unless your friend asks who is going. If he tries to vent and bash his former partner, gently try to steer the conversation in another direction.
Don't invite them to hang out at the same time -- even if they claim to "be cool" with each other. Until the dust really settles, hang out with your two friends separately. It will keep things from being super awkward and uncomfortable for all parties in the end.
Keep talk of the breakup among other friends to a minimum. While it is inevitable that you will discuss the break up with other mutual friends, be diplomatic and keep the conversation brief. That way you avoid having someone who is taking sides go back and say you were talking negatively about one of them.
Decide if choosing a side is necessary. If you knew one person before the other, and that person is really uncomfortable with you staying friends with her ex, consider how important she is to. If you truly value her friendship, you might have to let the other person go, according to life coach Dana Miller. If you have come to know the other person well and you have grown closer to that person, then it might be time to say goodbye to the first friendship.