Though I adore surprises and would encourage anyone to practice the art of second-guessing people's needs and desires, no gift giving guide would make sense without the caveat:  "When in doubt, ask!". Making sure is the best thing you can do if you feel out of synch with the person to whom you'd like to give a special gift. Sometimes you just don't come up with anything that feels right... That's the time to make inquiries.

This might mean forgoing the pleasure of giving a surprise gift. ...Though if you’re sneaky, you can often get the information you want! - from others, or through devious conversational gambits. If you don’t want your gift to have a negative meaning, and make someone feel bad each time she sees it (or feel guilty for putting it out of sight), some sleuthing may be in order.

But if cunning doesn't bring you the results you need, you'll just have to ask outright. Better safe than sorry! (And who knows, you might just brighten someone's day by allowing him to tell you about his innermost desires... or the embarrassing paucity of his tie collection!)

Oh, and always ask about a puppy.