Would you tell a friend she looked like shit in a particular dress?

At a birthday party this weekend I had an interesting conversation with another mother. I’ve casually known this woman for a few years so we often get into in- depth conversations when we see one another. She wanted to know what I thought of another friend’s decision to leave her husband. Before I could answer she said she thought her friend was making a terrible decision and had told her so… because that is what real friends do. I laughed, because that is something I would never do.

Then the conversation took an interesting turn.

Her: “Don’t you think you should let them know how you feel? Maybe it will make a difference. We should all tell her she is making a really bad decision.”

Me: “No, it’s not my place, even if asked I have no right to an opinion because I don’t really know how they feel.”

Her: “If a good friend came out of her room wearing an ugly blue dress it’s your responsibility to tell her because you’re her friend. The dress is a really bad choice and she should know and you must tell her.”

Me: “Nope, not true, what if my friend felt like a million bucks in the dress? Then I tell her I think it’s ugly. Then how would she feel? Maybe her feeling like a million bucks is worth way more than my opinion on the dress… and it’s just that, my opinion, maybe the next person will think she looks fabulous.”

Her: “But if she asks your opinion? Do you lie and say the dress if fine?”

Me: “There’s the difference, if she asks then maybe I will offer my opinion, but not without asking how she feels first. Does she feel good in the dress, does she love the color? Etc. etc. If she feels ugly in it then maybe I’ll say the dress just isn’t right… but until then, my opinion really doesn’t matter.”

Her: “That’s just being a bad friend… letting someone go out in an ugly blue dress.”

Me: “But what if the dress is beautiful to her and she feels like she has made a good choice?”

Her: “Doesn’t matter, a real friend would tell you the truth about the ugly blue dress.”

I laughed and now wonder, is she right? Would a real friend tell you your dress is hideous? Am I not a real friend because I can’t come right out and say the dress is ugly?