Last year, for a couple of weeks, my friend and I had a contest. The goal of the contest was to compliment as many women as possible. We met up every evening and compared stories. We developed a very intense set of rules: The compliment must be genuine (self-policing); eye contact must be made; friends count but only if complimenting something not normally complimented; and most importantly, the compliment must not be conditional.
When you are making it a point to compliment people, you quickly learn that there are two types of compliments. There are conditional compliments and there are unconditional ones. Conditional compliments are much easier. They are also really tricky.
Almost everyone would agree that “You are beautiful when you wear your hair down” is a conditional compliment. But very few realize that “You look beautiful today” is conditional as well. It’s tricky.
The worst part about conditional compliments is that they are easy. They are really easy. They take off all the pressure. When you tell someone they are beautiful today, it just means that you like the way they dressed themselves that morning. You aren’t saying that you find them beautiful all the time. You aren’t saying you are attracted to them. You are saying that you like their taste in clothes or something. It’s a wimpy compliment.
It takes far more of a man or a woman to tell someone that they are always beautiful, always intelligent, always caring, always thoughtful. And it’s those compliments that change lives.
Has someone ever conditionally complimented you?
Spencer J Smith 
To our generation, conditional complements ARE complements. It all comes back to the fact that we have lost a lot of our ability to communicate meaningfully, and that’s a real shame.
I have more faith in our generation than that. I think everyone just needs a little prodding.
It’s just so much more personal to given an unconditional compliment, I think. I mean, I’ll be suitably flattered if someone says how cute my outfit is, but it would mean so much more if someone were to remark positively about something that I can’t/don’t change. From the giver’s perspective, I know that it’s very hard for me to give compliments that are free of conditions if only because it’s an actual sign of affection that may be relatively deep.
Exactly the conundrum, I suppose.