In the world of relationships, there are certain feats we all try to accomplish. These include having a threesome, taking a trip together without attempting homicide and successfully meeting the parents.

None of these compare to the greatest feat of them all: trying to date an asshole.

See, there is a perplexing line between what makes a good friend and what makes a good boyfriend or girlfriend, and why they often can’t be the same person. This is particularly true in the case of the Asshole and his female counterpart, the Bitch. Why is it that we have no problem being friends with these people, yet have so much trouble dating them?

In high school I tried to date my best guy friend of three years. People had always said he was an asshole but I never saw it; I just thought he was funny. We broke up after two months. As friends we worked perfectly, but for whatever reason, throwing making-out into the mix led to catastrophe.

The obvious difference between these two relationships is the potential for baby-making. Granted you may not be actively seeking the father or mother of your future children, but subconsciously this role comes into play.

This is why I would cringe when that high school boyfriend would continually crush beer cans against his forehead, but had brushed it off when we were just friends. It was okay when he was just my idiot pal but not when he was the potential father of my future children.

The same can be said of a girl who gets in a drunken slap fight at a bar with some other chick who was wearing the same top as she is. If she’s your bitchy friend, you’re on her side, but if she’s your girlfriend, you’re pulling her back embarrassingly and wondering if she’ll still be bitchy to other women when she’s a mom. What is fun in friendships does not always work in relationships.

When it comes to the people we date, we have a deeper emotional investment than we have with our friends. When you date someone, he or she is a reflection of, not only yourself, but someone you might end up with in the long run. That’s a standard we don’t hold our friends to. Friends are the people you hang out with, but boyfriends and girlfriends are people you might have to hang out with forever. So we become slightly more selective.

A mistake we often make when dating the Asshole or the Bitch is thinking we can change them. Sure, they’ve dated other people before, but you are going to be the person that is different – the one that can finally get through and change them. After all, you know them better because you’ve been friends for years. But it rarely works out that way unless the Asshole wants that, too.

Don’t get me wrong. Assholes can be superb friends. We all make asshole comments in our head about that guy from the gym who sounds like he’s having an orgasm every time he picks up a weight or that random girl in your class who you’re pretty sure is plotting your death. Yet Assholes and Bitches tell these people what they are really thinking.

Even though you may have an absolute blast with your asshole and bitchy friends, don’t confuse that for a potentially awesome relationship. I know it seems like it could be fun and that you could get past their often inappropriate behavior, but assholes are always going to be assholes and bitches are always going to be bitches. It’s just in their nature. But keep them as friends, because chances are, one day you’re really going to want them around.

Kelsey Rohwer, a junior majoring in journalism, is a Hatchet columnist.