He’s Just Not That Into You: Personal Rules of Dating as a Guide for Doing Business

Dating is rarely straightforward.  To stay sane, I have developed strategies to help guide me through the confusion and frustration.

Business should be straightforward. But it’s not. Often, I find myself tackling the same issues. Is it too soon to call? What did he mean by that? It’s been weeks, does this mean he’s not that into me?

I wondered. What if I applied my personal rules of dating to uncomfortable business situations?

One golden rule of dating: The beginning of a relationship should feel mutual and effortless.

Even the best relationships have their challenges. No need to start early. It may be time to let go after a few dates if something doesn’t feel quite right. Even if the dates are thrilling. So far, this rule has well served me. Why not apply this rule to new business relationships?

I was recently introduced to a business contact who was described as “the one” to help A Sound Match move forward. I was intrigued and eager to connect. It took effort to get him on the phone, but we had a great call. He said he was interested and wanted to meet me. Only, it took weeks to reach him again to set up a meeting during the few days I was traveling in his area. Did I imagine his interest? At last, we arranged to meet with only a few hours to spare before my flight left town. Before we met, I felt skeptical about whether this guy was for me.

But … the meeting was great! We spent three hours together. I liked his ideas and energy. His enthusiasm for my business was clear. Working with him could be the very thing I needed. I was ready to get down to business and willing to overlook my initial skepticism. I felt thrilled.

Only, we met several weeks ago and I haven’t heard from him since. I emailed once and waited. It was tempting to reach out again. But, experience told me to step back to see if he liked me as much as I liked him. Guess he’s just not that into me. With little invested, the pain of withdrawal is minimal. Rather than get tangled in a new relationship that was already showing signs of pending confusion and frustration, it feels right to move on and find another relationship that feels mutual and effortless. No hard feelings.

Some people hate to date because of the rejection. I think it’s a gift. Over and over, the experience guides me through other important life decisions. Wouldn’t trade it for a thing.


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  1. Posted May 26, 2007 at 9:04 am | Permalink

    Stupid creative types. 😉

    (I wonder if he is an INFP, we do tend to be enthusiastic and then burn out quickly. Low burns projects are the ones we get done.)

  2. Posted September 21, 2007 at 12:42 am | Permalink

    Great point. Rejection is an inevitable part of the dating “game.” There are no insurance policies against it and there is no way to avoid it. If we make it a point to enjoy the process and treat each experience as a valuable lesson, our pain from rejection will turn into nothing other than great education.

    Arkady Itkin

  3. khutso
    Posted September 16, 2008 at 3:13 am | Permalink

    i am dating this guy he has a child and all is ok but comes weekend he disapears why