It might be an embarrassment when these activities are occuring in a third-world vacation spot renowned for sex tourism and you happen to be the most famous pontificator of social conservatism.
There seems to be a whole lot of denial on this thread, but I think most folks with half a brain know what kind of vacation this was. How interesting Rush decided to take his Hollywood friends on this all-male trip. This type of vacation is probably not terribly unfamiliar to them.
I don't think I'll ever again be able to listen to Rush rhetorically pander to those in his audience who believe that social conservatism and sexual restraint are vital to the future of society. At least not without chuckling.
I think you may be theorizing beyond the evidence. He said on his show that he carries them with him - I theorize (see, we all do it) that it's a little like teenage boys of my generation (and Rush's) used to carry a condom in their wallets: they had as much likelihood of getting a chance to use it as a giraffe did of sprouting wings, but that didn't stop them. I'd prefer to give him the benefit of the doubt that he's actually telling the truth about the reason for his trip rather than buy into a lot of hysteria about exotic sex trips to the Caribbean. As a woman, I can tell you Rush would have NO problem getting a date. Getting married is another thing; but getting a date - easy.