I was in the same situation a couple years ago and he is still thanking me for the present I got him... a total relief and surprize to me! (I just guessed, but I am glad it worked!) If your guy likes a sport a lot, especially if he plays it at school, he'll probably have a favorite professional or college team/player. If so, get him a jersey. Preferably of the college team/player, for "cool factor" (I've since been told). The wide price range of jerseys gives you the option of buying the basic or the special edition. My guy's now 16, so he just wants either cash for gas or a Visa gift card so he can go where he wants to get computer games. Come to think of it, the 14 yr old would probably enjoy the Visa card, too. Good luck!