Breaking up is hard to do. Not just for the couple involved but also for those close to both parties.
Even worse if you're part of a close social circle - because plenty of awkward situations are bound to crop up.
Do you choose one over the other? Should you invite both to special occasions? What if one badmouths the other and you're still friends with both?
It can be a very sticky situation, says Metro Counselling and Consultancy Services relationship counsellor Carolyn Midwood.
So tricky, in fact, that if handled wrongly, there's a risk you could end up with neither as a friend.
"It could become very uncomfortable," she says.
"If close to both of them, you may be expected to take the side of one person as they unpack all the horrible things they had to put up with.
"It is quite common for a friend to side with the person they are closest to and have known the longest."
If you are determined to remain close to both, there are some fundamental rules to stick by.
Firstly, do not be tempted to agree in sympathy with your bestie and badmouth her ex. If they reconcile, it could make the situation very uncomfortable, Mrs Midwood warns.
They may also be hyper-vigilant about any nuances that "confirm" you are taking sides, says Relationships Australia counsellor Mary Jo Morgan.
Listen to and comfort them but try not to give your opinion.
If necessary, tell them openly you do not want to choose, she advises.
"Listen but don't enter your opinion. Otherwise it could be a case of 'shoot the messenger'.
"Be an active listener and repeat back what you're hearing from them."
When it comes to functions where both parties will be there, or if you are unsure who to invite, be transparent with your feelings, says Ms Morgan. Tell them both that the other party will be invited.
"If you are not going to invite one of them, be open and honest and say 'I hope you understand'.
"You can't protect everybody and some people will get hurt in situations like this, unfortunately."