A long time ago, back home, I had a friend who was looking forward to marrying her boyfriend. I felt the boyfriend was a goof-off, and in no way good enough for her. I felt I should say something. As I was talking about it to another friend, my boss (at the time) overheard my plans for my heart-to-heart. He said, "Now why on earth would you go and do a thing like that?" I was incredulous. I said, "Because she's my friend and I care about her! She needs to know how I feel!" He said, "Did she ASK you?" "Well no..." "The only thing you're going to do is effectively ruin your relationship with her. She's in love with this guy, yes?" "Yeah." "And she is happy?" "Well... yeah, I guess but--" "No, no but. She's going forward with this, whether or not you feel like she should, and when you tell her she's making a mistake, she will make a choice. And that choice is not going to be your friendship. If you value your friendship, you need to support her and clam up about what you think is right or wrong for her." I was SO mad. How could he say that? He doesn't know! She's going to marry the wrong guy! But for some reason, I took his advice and kept my trap shut. That was many, many years ago, she is still my dear friend, and is still quite happily married to the goof-off, with a beautiful family.
Now don't get me wrong - there are those out there who will wait 'till the ends of the earth to say, "I told you so." But the people who love us will - wait - shouldn't ever do that. Every craptacular guy I ever dated in high school, or beyond, who broke my heart - my poor mom, who had to force herself to sit on her hands every time I walked out the door with one of them, every cringe-worthy moment she ever had about me being in the same orbit MUCH less the same room with them ... not a thing in the world would have made her say, "I told you so." When it all went downhill, as it inevitably did, she would always just be there, if and whenever I was ready to talk about it.
It's difficult, when people we care about ask for our guidance and advice - and because we care, we want to jump on their bandwagons and fly their flags. "He did what? You can do better!" Or "But you could date a girl 10-times hotter!" We want what's best for those we care for. Trouble is, sometimes they don't know what's best either. I have to remind myself that every day when I'm armed with an opinion I'm about to mow someone down with. It's been known to happen. Life lesson? Check.