I've never had that happen, but I'm usually pretty clear. If I invite a bud for a smoke, he or she knows what we're gonna smoke cause I'll say so. Or I'll say "I have a couple real special cigars for us", so they know the intent.
Conversely, I've been offered very special cigars that I've tried before, know I don't like, and I'll decline, very graciously. I'll just let them know it's wasted on me, but thank you very much.
Usually I'll drag out a bunch of stuff and say here, you need to try this. And this. And this...
I hate picking out cigars, cause I can never make a decision, so I like to send someone else in to pick us cigars. That's easier. I don't have any "special occasion" cigars anymore, cause every single day is a special occasion. So whatever they pick is special, because I know they're going to enjoy it, and they're going to be happy they picked something I'll enjoy.