(LifeWire) -- Whether you offer a sympathetic ear, provide a shoulder to cry on or drag a despondent buddy out for an evening on the town, your responsibilities are pretty clear when a friend goes through a breakup: Listen, lend support, and when it's time, help your friend pick up the pieces and move on.
But what should you do when you're friends with both parties? Where should your loyalties lie, and how can you avoid alienating either member of the couple?
Milena Perez, 28, was friends with both halves of a couple, and when their relationship of 1 1/2 years went south, she found herself choosing sides -- even though neither friend had explicitly asked her to.
"At first I did cease to talk and interact with the (guy), since it felt awkward and I didn't want to put myself in a difficult situation and make (my female friend) feel uncomfortable," the New York City publicist says. "It was my choice for just a small period of time until I felt the situation wasn't as intense."
Her reasoning was simple: "I sided with the person I was closer to, which happened to be the person I knew the longest."
In Perez's mind, there was no clear victim or villain. Although the split was emotionally difficult for both parties, the couple had decided together to end the relationship. Despite Perez's sympathy for both halves of the couple, her 10-year friendship with the girl trumped her 1 ˝-year friendship with the guy.
But what if the closer friend is the one you think is at fault?
One of Troy Swain's best female friends asked him to play couples therapist to help save her strained relationship. The 35-year-old market risk analyst and comic book artist from New York City reluctantly agreed, but with little success.
"The guy trusted me," he says, "but the girl took forever to recognize her mistakes, and by the time she recognized them, the guy was too (angry) and hurt to care."
"I think the girl was at fault and the guy had every reason to be (angry) and break up with her, but (she) is my best friend, so I sort of chose her side," he says. "Then again, I always tell her what I think is the truth, and I let her know that she (messed) up. And I told the guy that I largely agree with him. So is that really choosing sides?"
Caught in the middle
Holly Savoy, a licensed psychologist based in Charlotte, North Carolina, suggests some ways to take a stand -- whether you're an innocent bystander or half of the breakup couple.
If you're friends with the couple:
• It's really a personal choice as to whether you have to take sides, and who you should ally yourself with. "It is natural to feel a sense of loyalty to someone you have known longer, or have felt closer to, but staying neutral can be the best way to maintain a friendship," Savoy says. Moreover, "taking sides or talking negatively about the ex is likely to lead to loss of the friendship."
• If both parties seek to confide in you, just listen. To remain impartial, it's all right to listen to each person's story, but minimize conversations about the ex if you can.
• Set boundaries. If you're asked to pass messages between the two parties, "consider offering to let the other one know about the efforts to contact him or her, but not pass along specific details," Savoy suggests. "Let the couple keep those conversations between the two of them."
• Don't feel obligated. "If you are concerned that you might be caught in the middle, or in a difficult situation, it might be easier to suggest that they talk to someone else," Savoy says.
If you're half of the breakup couple:
• To avoid putting mutual friends in an awkward position, talk to your ex about how to handle the situation. "That way, as the couple, you are providing the lead to your friends," who also are likely to be confused or feel a sense of loss, says Savoy.
• Avoid talking badly about your ex to mutual friends. Save the trash talk for family members and close friends you had before the relationship started. E-mail to a friend 
LifeWire provides original and syndicated lifestyle content to Web publishers. Jocelyn Voo is a freelance journalist and relationships editor at the New York Post.
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