Comfy Pajamas and Chocolate (Score 2, Informative)

My girlfriend and I have been dating for almost three years. My favorite gift (from her) is comfy pajamas. I would never buy such a thing for myself, and besides my girlfriend has much better taste in such things. You don't even need to go somewhere fancy: just go to Sears, Walmart, etc and feel every pair of men's pajamas until you find the right one.

My second suggestion is chocolate. Everyone likes chocolate! I would not suggest one of those heart shaped boxes. Those chocolates tend to have too much sugar and not enough chocolate. I suggest El Rey, Lindt, or German Deli.com. Perhaps someone can suggest another good chocolate? If your boyfriend doesn't like chocolate, I think you should seriously consider dumping him. :)
If you enjoy wine, I would suggest getting wine to go with the chocolate. If you don't know how to match a chocolate to a wine, I suggest consulting the owner/operator of your local wine store.

Many geeks (and other men) get very nervous about Valentine's Day. Try not to make a big deal of the day. Tell him very generally what you plan to get him, so he know better what to get for you. It sounds like your relationship is still young, so he may not know how you feel about Valentine's Day. For example, if you spend your $100 and he buys a cheap heart shaped box of chocolates, he will not feel very good about this Valentine's Day. Tell him how you feel about him. Tell him that you enjoy spending time with him. Good luck!