Q: I’ve been dating my boyfriend for about three months He’s a great guy. Smart, funny, handsome, and he takes care of his own business. What girl wouldn’t want that? Unfortunately, he’s also a little rough around the edges. Occasionally it gets him into trouble. My family is pretty straight-laced. They’re not likely to be happy about me dating the “bad boy.” I want them to meet him, but I also want them to be proud. What should I do?

A: A tough exterior and a soft heart. That’s the kind of guy you want, in my opinion. He’s certainly nothing to be ashamed of. As far as your family, I’d think it comes down to the old saying: honesty is the best policy. Would I randomly show up with him at dinner, show him off, and surprise them with him? Probably not the best choice. What I would do, however, is prepare them for him. Start off slow: who he is, where he came from, how you met, and maybe even who is family is. Things like that. Believe it or not, but a lot of common ground can be built from those simply things.

If, after giving them a chance to know him through you, they’re still wary, then I’d bring him in. Sometimes face to face is the best thing. Not only are they liable to pay attention to how he is with you, but chances are, they’re going to speak with him. After all, you want them to know that smart, funny, and handsome guy that drew you in, too, right?

Above all else, your family probably wants to you to be happy. So if this guy makes you that, they’ll see it.

~ Bethany-Kris, author of The Arrangement and Lynked