Why Do I Make Girl Friends, but Not Girlfriends?

The other day my friend Claire asked me to set mousetraps for her in her apartment. Despite my hatred of cruel things like mousetraps, and my very comfortable position on the couch, I got up to help her out of friendly duty.

As I labored in her apartment, I thought to myself: "This is pretty easy. She could have done this herself." I realized I was doing "boyfriend duties" without boyfriend benefits. I ranted to my friend that she had to find a boyfriend to do this stuff, or make out with me if I'm going to do boyfriend duties.

I was kidding, of course, but it reminded me of my vast roster of girl friends (not girlfriends — one word, meaning a girl I actually date). I have one friend that I hired as my "manager." I made up a company: "Rich Santos Enterprises." Her duties include: keeping me company on boring errands, helping me paint my apartment, helping me with my spring wardrobe, helping my fruitless efforts to date women.

The Laws of Romantic Comedies dictate my "Life Manager" should watch me get hurt by approximately three girls before I realize that we are right for each other. That is, if she even thought of me romantically, which I know she does not.

The best relationships are based on friendship. So, I'm happy I have close female friends, but why can't I think of any of them as more than friends? Meanwhile, unavailable girl X, Y, Z with a boyfriend or mental affliction occupies my thoughts. And I'm interested in these types after only one or two meetings.

There are five things missing from my friendships that prevent us from taking the next step:

Timing — If you remain friends too long, you pass the line separating romance and friendship, and risking friendship in the name of romance is not a good idea. It's easier to take that risk before you've gone too far building a friendship.

Physical Attraction — There may be attraction before or during the established friendship, but you stop thinking of your friends in that way after a while. It doesn't seem natural.

Spark — Obviously, if someone is a close friend, you're happy around them. But the indescribable "spark" is the piece that drives passion and intensifies a relationship. It's even elusive in some serious romantic relationships from, let alone friendships.

Nervousness — You know that fun nervous feeling you have around a crush? It may be there at first with a new friend, but once it goes away it usually doesn't come back.

Mystery/Elusiveness — Once you're good friends with someone, they are no longer tough to get to. You don't feel "accomplished" getting them to hang out with you, and the challenge is gone.

Even if I decided to ask a friend on a "date," would she have any idea it was a date? We always go out to dinner, and hang out. So, I guess I'd have to explain: "This is different, it's a date." And if I didn't explain, maybe she'd never figure it out. Either way it would be awkward.

I bet most guys would try something with my girl friends. These girls are fun, cute, and intelligent. I become safe, gay shopping friend, and I can't figure out why. And it doesn't help that many of my other friends tell me I should "totally go for so-and-so" because "we get along so well," or because they "know we like each other".

Some of my friendships scream "girlfriend." I give them emotional support, I want the best for them, I'm there for them any time, any place, and I enjoy hanging out with them...and I go to their apartments to set mousetraps.

But I pursue the women I barely know, and most have boyfriends or some barrier. I'm hoping that someday a friend and I take another step into a relationship.

My friend told me about her girlfriend who kissed her guy friend, but it "didn't feel right" and they continued as friends. He moved away and she went to visit him. During the visit, they kissed again and gave it another shot. This time it felt right, and now they are married. So, I guess it happens, but I can't imagine that happening with any of my girl friends.

Do you date "friends" with more often, or is it the other way around? Why can't I take another step beyond friendship? How do you make that transition from friend to relationship? Does it happen naturally, or is it a clear decision that's based on some kind of defining moment?

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