What girl in her twenties doesn’t love a good old-fashioned bad boy? They’re charismatic, adventurous, and are just dangerous enough to get our blood pumping in a way that extends past our rebellious teen years. We often get our best stories from dating these kinds of guys; the kind of stories we smile and reminisce about 15 years down the road. It’s all fun and games, until you’re crying alone because he wasn’t able to be good enough for you. Let’s be honest, they hardly ever are.

But where’s the right place to draw the line? How do you know they’ve gotten too bad, and it’s time to get out intact? Don’t worry, we’re here to guide you through.

Don’t Fall in Love

If you can help it in any way, shape, or form, do not fall in love with a bad boy. I don’t expect miracles, no one can completely control who they fall in love with. But you do have a decent amount of control in the early stages, so that’s where you need to nip it right in the ass before it gets out of hand. Bad boys are created on the notion that they don’t need love …which is one of the things so endearing about them, I know. They walk around on top of the world. They don’t care what other people, especially women, think because they don’t need you to like them. Which is why you do. I know. Falling in love with one of these boys is just asking for heartbreak, and they won’t turn back to make sure you’re alright. Ever.

All the Right Spots

If you learn early how to handle a bad boy, he can be one of the most exciting experiences of your twenties (aside from potentially finding “the one”). Not only does he keep you on your toes, guessing, and embracing adventure but bad boys also know all the right things to say and with one look at you they can pinpoint all of your sweet spots. Emotionally and physically. And, he will use that to his advantage in a heartbeat …again, why you need to brace yourself before engaging him any further. “Dating” a bad boy has its perks for sure, but there comes a time where those pros go over the edge into con territory… or where they are heavily outweighed by cons the whole time.

When It Gets Old

In the beginning, you eat up every word he texts you, since that rarely happens, but three months of shitty communication makes a girl go mad. His unpredictability may be exciting in the beginning too, but another four months later you’re stuck feeling like you know nothing about him. Sure, the way he dabbles in a few recreational drugs is edgy and independent which can be attractive. But, when he can’t pick up the phone three months after that because he’s way too messed up to work his cell phone, you won’t think it’s so cute. I guarantee it. And of course, who doesn’t love a guy covered in bad tattoos who rides a motorcycle everywhere and doesn’t think he needs a “real job”? It’s everything rebellious wrapped in one gorgeous package. But in a year or two when he can’t pay the bills and you’re always driving because his motorcycle only fits one, you’re going to get tired of being the only adult in this relationship.

Meeting Family and Friends

Think about it. When you bring him over for Thanksgiving and Christmas, or whatever holiday you and your family spend together, how do you expect your parents to react to this guy? He’s someone who has absolutely no direction in life, and most likely gets off on treating you like dirt, because you’ll eat it up. (No judgment. We’ve all been there and eaten from that very silver platter.) But your family won’t find his bad reputation and attitude nearly as endearing. The same goes for your friends. Genuine friends have your best interests at heart, and while none of them are perfect, they can see things you don’t, especially when it comes to being blinded by a gorgeous guy.

At the end of the day, you should always do what makes you happy above what other people think, but take into account the opinions of your friends and family, especially when they coincide.

Making a Decision

What’s the logical thing to do? Make a pros and cons list. It’s as old as time itself, but it works. You’re forced to put on paper (or notes app) the qualities you like and the ones you dislike, though granted you may write that you like what a jerk he is or how dangerous he is. But think about it this way; if you’re embarrassed or uncomfortable at any point while making that list, and don’t write down those embarrassing uncomfortable thoughts, then you aren’t being truthful. If you are avoiding being truthful, there’s something very, very wrong in this relationship.

If his bad boy tendencies have overstayed their welcome, and are no longer new and exciting, it’s time to drop him like a hot plate. If you’re lucky, you’ll find your own version of Prince Charming that’s a good guy with just a sprinkle of bad on top.