Is It Too Much to Ask for Looks and Personality?

This past weekend my buddy and I were at happy hour chatting with a woman at the bar. I was impressed by how interesting she was, and particularly astounded by the following three things:

Helter Skelter, the story of the 1969 Charles Manson murders. Most women I know call me weird for reading it, but the woman at the bar had read the book.

my recent argument with my friend over Lady Gaga in which she called me "close-minded."

It was one of the best conversations I've had with a woman lately, but there was no physical spark. For me, the physical spark is either there or not in the beginning, and never develops over time. So, my buddy and I left the bar lamenting that she was "so cool," but "not hot."

It reminded me of a phenomenon I encounter in my dating life:

Whenever I meet a girl I enjoy talking to, she's not physically attractive. Whenever I meet a physically attractive girl, she's not fun to talk to.

I've come up with a couple of questions to try to understand this:

Can cute girls talk about "boy stuff"?

OK, maybe my "boy stuff" is weird: horror movies, serial killers, porn (I admit I should leave that one out of conversation). But I also make an effort to be able to talk about stuff my guy friends don't talk about, like cooking, pop culture, fashion. I guess it's tough to find a hot girl who can not only handle my weird "boy" subjects but keep up and contribute.

Are good-looking people enabled to get by without having a great personality?

Many women I know have the following boyfriend in their ex-files:

"He was so hot but he had nothing to say. I got bored with him after a while."

I believe most people have the capacity to learn and develop their mind. But maybe hot people don't have to try too hard to get what they want. In other words, someone like me who is not confident in his looks better have a darn good personality. I can't walk into a room and just look good. Hot people can, and maybe they don't have as much need to develop their personality.

I may be shallow because I only date women who are physically attractive to me, but I don't particularly enjoy making out with a hot girl who has no personality. It's an empty experience based on aesthetic pleasure without mental/spiritual connection. Hot people should have to prove they have a great personalities — even the hottest girl would get boring after a while if she had no personality.

Should we expect our significant other's personality to turn our world upside down (in a good way)?

It seems like most men look for a woman to help them "feel like a man," and women look for men to help them feel beautiful. Lately, I've been looking for a woman for a different reason: I'd like to find a woman who enlightens me.

Most people find enlightenment in museums, music, books, movies. Perhaps the majority of people are not looking for their significant other to do so. Personally, I'd love to be enlightened by a woman.

My friend told me that I'd eventually find someone interesting AND cute but "you can never get everything just right." That discouraged me.

When I told that same friend I intended to take the original Texas Chainsaw Massacre over to a girl's house for a movie night, my friend told me: "She's not going to appreciate it the way you appreciate it. She would be freaked out."

Me: "So, she wouldn't buy into my observation that the movie has incredible pacing?"

My friend: "She wouldn't know what pacing is. There are certain things you just shouldn't discuss with certain girls."

I guess I need to pick up Titanic or Sex and the City for a movie night, but boy would I be bored.

Maybe I'm looking for a challenging woman who fills in little blanks/voids in my mind and life. It sure is tough to find a pretty girl who can do that.

What are your thoughts on my argument above? Do you agree with my philosophies, and do you run into similar problems in the dating world?

Follow me on Twitter: twitter.com/richravens