A few years ago, for example, when I went to see the play my girlfriend had done stage crew for, and she asked what I thought of it. She wasn't satisfied with my initial noncommittal answers, so she pressed for more. Not in a "trying to start a fight" way; I just wasn't doing a good job of being evasive. I eventually gave in and explained why I thought the acting had sucked, which did not make her happy. I think incidents like that must have contributed to our breaking up shortly thereafter. The breakup was a good thing for other reasons, but I still regret not lying to her about what I thought of the play.

Boy, I sure wouldn't want to date a person like this (your girlfriend-at-the-time). She asked for your opinion; pressed you to actually give it, thus communicating (by any reasonable measure) that she actually wanted your opinion; and then, when you gave it honestly, was unhappy about it? That's horrible.

I don't think I'd ever willingly choose to be close to someone to whom I'd ever regret not lying in response to being asked for my opinion. The thought of living like that, living with the knowledge that honest communication is basically impossible because any time the person asks me (and presses me) about my opinion, I have to consider the possibility that what they actually want is lies — that this person prefers lies both to truths and to no comment — repulses me.