The Art of Letting Your Inner Monster Out at the Right Time

I recently emailed a girl I don't know too well and "ornamented" the email with a joke. Of course my instincts are never correct, so I had my friend Margaret drop by my desk at work and assist me with editing. My clueless...

I recently emailed a girl I don't know too well and "ornamented" the email with a joke. Of course, my instincts are never correct, so I had my friend Margaret drop by my desk at work and assist me with editing.

My cluelessness was evident by all of Margaret's cuts. After we were done, I felt like a spurned author who had over 75% of his manuscript sliced and diced. I tried to argue some of the changes, and Margaret either argued back or just said: "Um, no."

She asked me: "Now, isn't that nice?" I read the final product over and I must say — she made it much better.

This process got us talking about the games we play early on during courtship. I explained to Margaret, in light of the upcoming Kentucky Derby, that in the beginning of courtship I feel like one of those caged horses in the stall right before the doors open and the race starts (sadly, lately, I've been more like the spooked horse who doesn't even want to get in the stall). I'm full of potential energy, waiting to be released...and I'm very impatient.

Because of this "caged feeling," I have to fight the urge of giving up "too much Rich" in the beginning, or being too forward. As Margaret explained:

"You need to show her all of the wonderful things that we like about you first so that she can take on the more challenging things later after she loves the great things."

"Challenging things?" I asked. I wondered how someone as perfect as me could be challenging.

"The tardiness, the immaturity, the not listening..."

"Okay, I get it. You can stop," I said, disheartened.

My friend Chris, chimed in: "You know how you have to do this. Women do the same thing. At first a girl seems cool because she doesn't mind when you hang out with your friends and all. Then, all of a sudden, they don't want you hanging out with your friends and doing your thing. It's like clockwork."

So apparently guys and girls in successful relationships are keeping their more "challenging" traits to themselves until this magical moment (some say it's the six-month anniversary). Perhaps something that was once a deal breaker is no longer a deal breaker after six solid months of dating.

For example, a friend told me that her friend had just moved in with her boyfriend when she literally caught him biting his toenails (why he didn't have enough self-awareness to know that biting toenails is something that should be done behind closed doors is beyond me). She asked him a few questions about it out of curiosity but didn't explicitly tell him to stop. He continued biting his toenails, and they continued living together. Pretty sure that discovery wouldn't fly on a third date.

People are more forgiving of others they have known for a long time because of energy/time invested in the relationship and, as Margaret stated, they love enough good things about that person to outweigh the bad — toenail biter must have some REALLY great things about him to offset his strange habit.

When I finally let out "the rest of Rich Santos" to some poor girl, it will be as if she is crushed under an avalanche of all my terrible characteristics that were crammed in a closet at the last minute before I started dating her.

I do agree that too much info up-front can be overwhelming. But what do I hold back? The bathroom humor? My love of the original Texas Chainsaw Massacre? Do I hide my two giant cats for six months whenever she's at my apartment?

I believe in "be yourself." Perhaps it's actually "be the best you can be for six months...and then be yourself." I'm going to try it, but something doesn't feel right about hitting someone with the following at the six-month mark:

"Oh by the way, I have terrible ADD, I have trouble listening, I'm kind of immature, and I have these two giant cats that love sleeping in the bed, so they will sleep with us moving forward"...most likely not what she signed up for.

What are your thoughts on the "Six-Month Rule"? Do you agree that it happens? What are the worst things that you found out about guys later in the relationship that didn't drive you away? What characteristics do you try to hold back in the beginning?

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