Making the Difficult Decisions With Friends

In my mind there is one really standout moment where I had to make a very difficult choice about how to support one of my friends. I had to decide which of two bad decisions was most supportive of what I knew my friend’s goals to be.

Back in 2006 I received an unexpected phone call from one of my friends. She wanted to talk to me about her boyfriend. Her boyfriend is one of my closest friends, both then and now.

She was on the fence about whether she should break-up with him. Part of her felt like the relationship was stale and had run its course. Part of her felt like they had a good thing, albeit not excellent. She felt like the fact that they didn’t live in same city was a problem, but she also liked the freedom that built in.

We spent well over an hour and a half on the phone. It is a supreme oddity for me to talk that long on the phone. We talked about her actions and his actions, her feelings, my thoughts, my shared history with both of them and so much more.

At the end of the conversation there was no clear answer to what was going to happen. While she felt much more comfortable having talked about it and being very thorough in thinking about it, she still hadn’t decided what she wanted from the impending conversation with her boyfriend when she went to visit.

This is where the situation became most difficult for me. I was faced with a decision that felt like a catch-22: should I tell him that I had this conversation?

On one hand, I have always believed that forewarned is forearmed; on the other, I felt loyalty and affinity for both parties. What if she decided that she didn’t want to break-up with him? What would happen if she decided not to even bring it up during that trip?

Not telling him seemed like it would make him mad at me. Telling him seemed like it would cause him to stew on the issue, or confront her and make things worse. I knew for a fact that this was the girl he planned to marry.

I told her that if the fight got heated (I was pretty sure it would) that it was okay to tell him that she had talked with me. To ask him if he thought there was anyone who would have done a better job advocating for him and his interests in the relationship.

In the end I chose not to tell him anything. At the end of their weekend together I heard from both of them. She thanked me for talking with her and letting her throw me under the bus. He told me that he understood why I made the decision that I did, that he couldn’t really offer any good alternative, and that he didn’t want to talk to me for a while.

So, what about you, what would you have done?

5 thoughts on “Making the Difficult Decisions With Friends”

  1. Totally would’ve done the same thing. You did the best you could for your friend with the information you had. Depending on the circumstances her call to you could’ve been meant to get back to your friend so he could know her feelings before she saw him. Like maybe she wanted him to be prepared for having the conversation. Sounds like that wasn’t the case here but I’ve had it happen to me.

    Good on you for making the right choice.

    1. It is nice to know that there are other people that have the same thinking as me. Balancing what is right in the short term and what is right in the long term is often difficult, especially when it affects someone else’s love life.

  2. I remember the anguish you felt with the role you were cast into with these two very good friends, but it apparently helped them work things out. Are they still together?

  3. From similar experiences, I now try to be up front at the beginning of conversations like that. I let the person know (and they understand and agree) that it puts me in a difficult position. I request that they tell the person in X amount of time that they had the conversation with me and that, if they don’t, that I will tell the other person out of loyalty to them and our friendship.

    If they’re not ok with that, then it’s probably best that they have the conversation with someone else.

    There might be better ways of handling it, but that’s the best I’ve found so far.


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