When is it ok?

[AGDee]

Your best answer in that situation is "I just want you to be happy. If he/she made you happy, then I am happy for you. If he/she can't make you happy, then I hope you can find someone who can." Thankfully, I used that line when my dad and his girlfriend (who I hated) broke up because she is now his wife. Stay diplomatic.

[valkyrie]

I'd tell the truth as tactfully as possible. Instead of saying "Man, she was a harpy bitch from hell," I might say, "Well, she did seem a bit controlling at times, like when she told you you couldn't have any more beer that night we were heckling Barry Bonds."

I consider it my duty to be honest with friends on important issues, even if it isn't always easy or what they want to hear.

[AKΨ_BRO@DSU]

Both of your answers are good and I've previously considered both of them if the situation were to arise. I was leaning more towards diplomacy because of the fact that they could get back together at anytime and I don't want to seem like I'm hating...however, I have considered being completely honest because if I could show my friend what I've noticed and why I think he made a good choice, then I could save him a lot of wasted time by getting back with her....I dunno .

[OtterXO]

My thing is, if the person asks you about it then you should give your honest answer. Obviously don't be a jerk about it, but be honest. Most people know that friends sometimes see things they don't and if you're not rude or offensive then they shouldn't take it the wrong way. There's no sense in lying to your buddy and acting like you thought the girl/guy was really good for them, you know?

[AKΨ_BRO@DSU]

Yeah. I never planned to lie to them, just kinda dance around the issue, lol. But honestly, its not them taking it the wrong way that I would be worried about, it would be how they would view my outlook on the relationship if it were to start back up.

[Drolefille]

I guess it depends, did you hate that person, or were they just not right together... That makes a big difference on the telling the truth aspect.

[chitownxo]

I had this situation with my best friend from high school, who was like my sister. A couple of years ago, she got involved with someone, as my grandma would say wasn't a quality person. In simple terms, he was, and still is, a dirt bag. He worked less than Kevin Federline, stayed in bed or played video games till 2 or 3 in the afternoon, all while supposedly writing a screenplay that would set Hollywood on fire as she supported him by working two jobs. He also hit on all (and I mean all) of her friends, "borrowed" my then boyfriend's credit card, and made fun of my mentally retarded aunt at a family gathering. They broke up, and she asked me what I thought of him. I told her exactly what I thought of him.

Guess what? They're married now. Once they got back together, she told him everything I said about him, and now we don't speak since he convinced her I was jealous of their great realtionship. Yeah, sure. I don't miss him at all (and am looking forward to his future apperance on an episode of Cops or America's Most Wanted), but I do miss her. Looking back, I could have been a little more tactful. That is, instead of saying, "He's a slimeball leech with a serious hygenie problem", I could have said, "I worry about his lack of ambition".

Lesson here is: be tactful or stay neutral.