When does "Its o.k. – don’t worry about it" mean more?

Lets talk about the various meanings of “Its o.k. – don’t worry about it”. It seems like it would be a simple phrase, but it has many meanings. For example, if you break my $1 stemless glass at a BBQ at our house and I tell you its ok, don’t worry about it, I mean it. Really, I have no interest in you giving me a dollar or trying to find a replica. I’m serving wine out of $1 glasses because I don’t want to care if they get broken.

But what if you broke a special commemorative glass that I got from a winery, a signed bottle, or even just a decanter? Would I still say “Its o.k. – don’t worry about it” as you fell over yourself apologizing? Probably, but the meaning is different. In the $1 stemless scenario above, I mean please do not worry about replacing it, its really ok. In the scenario where the item costs significantly more than $1 or holds some sentimental value, I mean don’t worry about as in don’t stress about it, stuff happens, I’m not going to be mad at you for breaking it (well, not for long anyway). But the underlying thought is “you broke something of mine, please replace it”. Often in that scenario I really don’t want money, particularly if it’s a gift or a commemorative item –because its just strange to receive money from friends, but that's me.

Now, the next question is at what price point does the ““Its o.k. – don’t worry about it” really mean “don’t worry about it as you quickly go get me a replacement”? I’m not sure but I’m thinking $10+, because if I was at your house and I broke something of yours that had an appearance of $10+ in value, regardless of how many times you told me “Its o.k. – don’t worry about it” I would still get you a replacement or a bottle of wine - something. Accidents happen but I don't want you paying money for my clumsiness. I’m not sure how I would handle a commemorative item, so please don’t let me handle them after drinking! ;)

If you’re reading this and are wondering what of mine got broken that I’m whining about - nothing. My decanters, bottles, and glasses are intact. Well, I broke my own glass by clicking my teeth on it last Saturday which ended up in a near glass chewing incident, but that doesn’t count. :) I’m just musing about wine social niceties.

What do you think? When does “Its o.k. – don’t worry about it” really mean more than that??