Age is a tricky thing, because so often age and maturity don't go hand in hand. Someone who's a senior could be totally immature and think acting out scenes from Jackass is the height of comedy, whereas a freshman could be able to handle difficult situations with aplomb, have intelligent and thoughtful conversations, and generally be advanced in plenty of ways. The only way to know is to spend time with the person and see who he is, what he's like, and whether you two have a connection. If you like this guy, there's no reason to hold back on trying to get to know him better just because of an age difference. Sure, going out with someone in another grade has its challenges, such as having a different group of friends and being at different places in your lives (he's just getting into the swing of high school life, while you're looking ahead to stuff like senior year, graduation, and maybe college). Still, you've got nothing to lose by getting to know him better.

As for your mutual shyness, all we can say is that you should try to relax, be yourself, and absolutely be friendly whenever you see him. Smile at him in the halls and wave hello, or if you know people in common, try to go up to him when he's with them, which is a nice way of approaching him without feeling like you're going out on a limb. If you don't have friends in common, you may have to work up the nerve to talk to him when you see him, otherwise you'll spend a whole other year waving and smiling and never getting anywhere. Once you guys get a chance to speak, you'll both warm up and be able to have a good conversation and forget about being bashful. After that, you'll get a chance to see if your freshman is mature enough for a woman like you!

—Andrea Pyros