Why Dating an Asshole is Good for You: Part 2

Dating an Asshole

I originally wrote about this over three years ago, why dating an asshole is good for you. It's good for your soul, or something like that. Maybe you didn't agree with that article, but I'm back a few years later to tell you that it still holds weight, that it's still true to this very day. Why? It's hard to say. When I wrote that original piece, I was referring to myself. Today I write this because I'm dating a self-described asshole; actually she calls herself “cunty” more often than not. She asks ME why I'm so nice to her?  She has a point because she is sort of a bitch. It's funny, because I don't think I'm all that nice. All of my friends are jerks—and I love them for it—I cannot help but be attracted to women who are strong, speak their mind, and don't take any of my bullshit.

I recall going on a date earlier this year with this beautiful woman. Very talented; highly educated; had a great job that allowed her to do what she loved and she was interesting as well as engaging. I couldn't care less. Perhaps there were some parallels I had drawn to past relationships; but I don't really think that was it. I was bored. The conversation came a little too easily, she laughed at ALL my shitty jokes; it was to the point where wiggling my thumb made her laugh! Now, I have to be clear. There was nothing wrong with this woman at all. Not one bit. If anything, it's telling that I wasn't interested, it's a me thing; it's telling that being too nice and too accommodating is a thing I don't like. I like to “work for it.” I like a challenge. While this woman would certainly challenge me in every way, romantically and intimately, it just wasn't happening.

I live in my own head a lot. I think I'm doing amazing work and amazing things in life. In fact, I'm hustling just like so many others who do what I do. I'm not doing anything special, I'm not. I just do what I do to get by. I mention this because I know that sometimes I get lost in my own hype and I live this gimmick; that I'm some great business dude who likes good things, dresses well, and drinks great booze.

The fact of the matter is that I sorta dress like a bum, I don't know what the fuck I'm doing and I should buy new boxers. I drink Hendrick's Gin like it's the best stuff on earth. Some disagree; and some people are assholes, so I go on thinking Hendrick's is wildly delicious. I run a non-profit—okay, it's not a “non-profit” it just makes minimal profit. The point is to not take ourselves too seriously. The point at which you do I hope you meet an asshole, or better yet that you are dating one.

An asshole will tell you “no” and not even feel bad about it. An asshole will stop you cold and tell you what they're feeling and leave you to sort through it. No bullshit, just a clean “No, now fuck off already!” Harsh, maybe? Sure. But I'd rather know where someone stands than to continue doing things that might annoy or even make someone feel disrespected.

An asshole will knock you off your carefully crafted pedestal. I am a delusional person to some degree and I'm sure it's to a larger degree than I can admit to. The asshole I'm dating pokes fun at me; makes barbs and sometimes that shit is annoying. But you know what else is annoying? Taking yourself too goddamned seriously. It's okay to have your ego deflated; go on, suck it up and own your mediocrity and your shit choice of Gin.

An asshole challenges you and they won't even be trying… You ever talk to someone and they say something that catches you like a deer in headlights? An asshole is typically someone who has strong beliefs and opinions—well-formed and can articulate a solid argument, regardless of whether or not you agree. This challenge isn't about competition; it's about looking inside of yourself and working on you. Truly. We can easily get caught in our own shit that we have to do that we forget to learn; we forget to listen and we forget to be present.

An asshole knows that they're an asshole and they're only treating you the way that they do because they feel comfortable around you and feel like you can take it. They know who they are and don't need to play to your baser instincts. They will tell you like it is and if you don't like it, then you fucking deal with it and get bent.

An asshole also knows that they themselves are the ultimate asshole. Sometimes you need to shove their shit right back at them and give them a healthy dose, with no sugar to make it go down easier. Assholes appreciate, more than anything, someone who can a) “hit back” and b) can be honest. Honesty is big for any sort of person. The asshole realizes the dynamic of having a difficult discussion, even if they aren't super great at them.

Breaking it down

Dating an asshole is more about you than it is about them. What I mean is that in all aspects of life we need to challenge ourselves; whether that's in our fields of study or work; whether it's in our hobbies, and especially when it comes to who and how we love someone else. Lastly, it comes down to how you live your life and how you carry and love yourself. It's important to understand that we are beings in pursuit of something. I know it's cliché, but it's true. We seek truth, love, inner-peace, great art, great sex; whatever it is. I think that, to me, being an asshole is truly a state of being honest with yourself. Yes, I just talked about being an asshole is akin to some sort of spiritual space. Maybe it is.

Dating an asshole is an opportunity to learn something about yourself. Don't run from that.

Author profile

Alex is the founder and managing editor at the Urban Dater. Alex also runs: DigiSavvy, for which he is the co-founder and Principal. Alex has a lot on his mind. Will he ever get it right? If he does, he'll be sure to write.

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