There's two ways to go about it. There's only two ways. Never get caught half-pregnant.
How do you choose a wine as a gift for somebody else? If you know the person you're buying it for is going to go on Google and look it up or is pretentious, buy him a brand name, something you know, Caymus, Cakebread, Dom Perignon, Santa Margherita, whatever price range you're looking for.
Or go the complete opposite way. If you know that it's somebody cool, laid back, or into wine, go very nerdy. Weird wines, you know, from Greece or Hungary or the South of France, because that's kind of interesting and new too, and you're expanding somebody's palate.
And the way to execute that, by the way, is to go into a wine shop and say, "What's the nerdiest wine you've got?"