Should I Date Him?

He's a mess, he's trouble, he's a bad boy, which means one thing: you're young, and you haven't made some pretty critical mistakes just yet. Honestly, you shouldn't date this guy, but you're probably going to. All that we'll say is that it will be a whole ordeal, but you'll learn a lot about what you don't want in a serious, lifelong relationship. He's not Mr. Right, and he never will be. But to get to Mr. Right, you have to learn why wise women don't date mean boys.

It's obvious that you really like this guy, and he's really into you. In fact, he seems like he has some good intentions! But there's a catch: there's some sort of obstacle in the way. Maybe his work schedule is tough to deal with. Maybe he goes to school and work, which leaves little time for dating. It could be anything, really, even residual feelings for an ex. So, our suggestion? Wait it out. Flirt here and there, see him, spend time with him, and when he's ready, he'll ask you out.

He's so adorable! And you really like him! The things he does for you show that he cares, he's in it for real. He's trying hard, and you totally have the power to make his year, if not his whole life, by going out with him. Our suggestion? Put on your best (but casual - don't try too hard) outfit, and just be yourself next time you see him. Be a little flirty, even if it's just in how you use your eyes. And he'll get the hint!