08/17/2012 09:47 am ET Updated Oct 17, 2012

Dating Fears: 'I Don't Know The First Thing About Choosing The Right Guy'

Well, it's been a while since I've been in the dating game, but here I am. And although I'd like to say I'm better than ever, that would only be half true. A little more than six months ago, I came out of a three-year rollercoaster of a relationship -- you know, the kind where you break up, then get back together, only to remind yourself why you broke up in the first place, and then ultimately break up for good? Yeah. So it was out with the old and in with the new: new job, new plans, and a new perspective.

My professional life is right on point, as it always has been. I have found a job that suits my type-A personality just right. Meticulousness, acute attention to detail and coping with craziness are all right up my alley. Am I surprised? No. I've always known EXACTLY what I've wanted to do career-wise. It's always been so easy for me to navigate my way through life in the professional sense. My personal life, however... where do I begin?

I don't know the first thing about choosing the right guy. I'm great at giving advice -- I advise my friends like it's my job. So why can't I ever get it together for myself? I wouldn't say I pick bad guys necessarily; I tend to pick guys who are needy. Even the word "pick" is the wrong word to use in my case, because I don't seek these guys; I seem to attract them. Like a moth to light! Funny, I don't remember having a sign on my head that says, "Mama's Boys Need Apply."

Really, though, they're not bad guys. They're mostly looking to fill some void the same way I am. Something a shrink would classify as a lack of love or nurturing during our childhoods. Thanks, Mom and Dad.

I guess the best way to back this up is through examples. Allow me to indulge you in the tale of my last "relationship" -- one I'd like to call "The Build Up."

I had my eye on this guy while I was working at my previous job. I had a boyfriend at the time, so it was simply admiring from afar. He worked on my floor, so walking out of my office and running into him at the elevator bank was certainly a guilty pleasure of mine.

He had it all goin' on.

About 5'11"? Check.

Beautifully coiffed hair? Check.

Glasses (on occasion)? Check.

Perfect teeth? Check.

Nerdy? Check.

Seemingly good job? Check.

Cute butt in work pants? Double check!

Jewish? (No, I'm not Jewish, I just have a thing for Jewish boys) -- Check!

He even had a nickname: "Cute Guy from Elevator." So I'd see Cute Guy from Elevator from time to time and imagine running my fingers through his awesomely fantastic head of hair, which of course was soft and just as perfect as he was. Now this was all good and fun, until I did what many girls tend to have the habit of doing: building a guy up in their head without even knowing anything about him. As perceptive of a person as I am, I totally prejudged this guy based on his image and demeanor alone. I mean, he looked great on paper and he was great looking; what more could a person want? Assuming his persona was my first mistake. Just because someone seems like they've got it all together doesn't mean they do. He came off as confident, strong and smart -- which is what drew me in -- but once I got to know him, I realized there was so much more complexity to this person than I ever could have imagined.

Check out my next post for more....

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