Is Overthinking a Relationship Ever Good?

The reason I screw up so much is that I ignore my good instincts and follow my bad instincts. I need to figure out how to just follow the good ones. People like James Bond, Han Solo, 2008 Rich — superstuds. They just make good decisions and don't make mistakes.

Here are two examples of ignoring good instincts, and one bad instinct that I have ignored but I fight every day:

Cheese Girl

One summer I worked the deli at a Whole Foods; I was the rotisserie chicken guy — definitely not the type of job that attracted many girls. However, like a circus, the workers at the supermarket all had this strange camaraderie. So, it was this one magic summer when I had a chance with this really hot blonde who worked in the cheese department. With some prodding from my boys behind the deli case, I worked up the guts to ask her out. And, because we both were stuck in that supermarket — and ONLY because of that — she accepted.

We went out to dinner, and when the waitress came by to take our drink order, my date declined. I found this odd; I thought to myself:

There's some reason that you should NOT pressure her to order a drink.

But, inexplicably, the following came out of my mouth:

"Come on, you can have one beer."

After she declined for the third time, she finally admitted:

"I really can't. I'm a recovered alcoholic."

At this time in my life I did not know much about alcoholism. I figured: Because you are recovered, you can now drink in moderation like any person who is not an alcoholic. I did not realize that a recovered alcoholic should never drink again, not even one. My instinct continued to plead with me to stop pressuring her, but I still ignored it and I don't know why:

"So you're recovered. Doesn't that mean you can have ONE?"

My date spent the rest of the time at dinner explaining alcoholism, and the implications of recovery. Obviously, we never went out again.

Morning-After Rudeness

The third girl I ever had sex with was a friend from high school who visited me at college. Of course, I forgot to wear a condom.

The next day I was extremely worried that I might possibly have AIDS. The droplets of fear replicated in my mind hour by hour. I contemplated calling the girl to ask if I should be tested.

"No, you canNOT do that," I told myself. "That's rude — just get yourself tested if you're worried."

On the other hand, I figured, in this day and age, you're totally okay calling someone to ask about testing. I decided to call her.

The conversation took about two minutes. What could have been a respectful day-after-sex-check-in call turned into:

"Do you think I need to get tested?"

"I cannot believe you have the nerve to ask me that."

She has hated me ever since.

First-Date Stupidity (Waiting to Happen)

Because I work in advertising, I get a lot of great free dinners and gifts from publications that want me to consider them for my clients. Every time I get a good restaurant gift card, I contemplate asking a girl out so I can use the gift card to pay for dinner.

I think it's kind of lame to pay with a gift card on a first date. But it's almost like I can't stand NOT to be lame. I keep thinking about trying it. The girls at my work ask me:

"Do you WANT to fail with this girl? Then pay with that damned gift card."

Maybe I should just hold the cards for when I've strung some dates together with a girl. But paying attention to my better instincts is so difficult for some reason.

When I play sports, I do fine with my instincts because there is no time to think. Given too much time to think, I talk myself out of good instincts and into bad ones. This is the main driver of my self-destructive behavior.

It's tough, because first instincts can be too much of an impulse, but overthinking can lead you into the wrong decision. Perhaps I should just go with: When in doubt, don't do it. Maybe I just have to make tons of mistakes before I know exactly how to do the right thing.

Do you think it's best to listen to your first instinct and then close the book on the discussion? Do you run into trouble when you overthink things? Do you have any examples of ignoring the right instinct and ruining what could have been a good thing? And ... is it lame to pay on a first date with a gift card?