The Best Date That Never Should Have Happened

Despite the latest trend offered in online dating apps that allow people to swipe left and right, almost as if finding a date is as commoditized as choosing pair of Nikes on eBay, I still believe online dating. Finding a life partner online can happen, thanks to browsing, reading, screening, interviewing and pragmatism. Particularly for single parents who want to do more than hook up, there are several mental “check boxes” (as a close single mom friend describes it) that online dating profiles can help you complete. This sort of data can help someone drill down into the criteria that matter most. Still, there’s only so much one can discover by reading a dating profile and having a brief conversation. I find that until I’m sitting with a woman in a quiet, comfortable environment, there’s just no other way to be sure about chemistry, and all the senses that come into play.

Having said that, it’s easy to get distracted by an attractive online profile, overlook a critical check box, and find yourself on an exciting date that you eventually realize isn’t right for you. Frankly, I don’t have time to do that, and I know most single parents feel the same. Below is the story of a very good date that never would have happened, had I not allowed myself to overlook one very important criterion.

I met a woman in Manhattan Beach after we found each other online. Looking at pictures, reading essays and having a brief phone conversation had all gone well, so I was looking forward to meeting her. As I drove to the restaurant I had the familiar feeling of cautious optimism borne out years of dating experience. It’s easy to start imagining, “This could be the one,” before you even meet, based entirely on pictures and a few important details, and that’s exactly where my imagination went on this particular night. I wasn’t thinking about the unchecked box, obviously.

My date was a beautiful woman in her late 40s, with long blonde hair that looked like spun gold, bright blue eyes and a smile that seemed to light up the room. As she talked about her unsuccessful and intermittent experiences with dating, it was clear that she wanted something good to happen and that she was comfortable with me. She was right there in the moment, being her most charming, present and open self. Both of us were asking, listening and curious. We had nothing to lose, and everything just clicked.

What struck me most was that she didn’t worry about what might or might not come next, and so I found it easy to settle into the same frame of mind. We revealed some of our life stories. We talked about our successes and our losses. We also talked about how easy it is to let attraction and chemistry preclude real intimacy, and simply jump into a physical experience that can create false intimacy. We covered a lot of ground!

But here’s the thing. Although it was clear that we were very attracted to each other, I started doing calculations and projections into the future, and all I could see was this one unchecked box sort of suspended above her head, slowly turning in an ominous way.

I walked her to her car, and I simultaneously thanked her, said goodbye and gave her a hug. She surprised me by holding on to my forearm as I was letting go, and asked me point blank, “What do you think of me?” I could tell she didn’t want to wonder if she would hear from me again. I didn’t have the words at first, and I glanced to the side as someone walked passed us a few feet away, providing the momentary distraction that made my delayed response seem like discretion. As I started to speak, she interrupted me to say she wanted to go out again, have dinner, see a movie, have sex and she didn’t need to know what was next. You read that last sentence correctly. She put sex right between a movie and total uncertainly about what might come next. She told me how much she appreciated that during the date I listened to her, that I was interested in her. Suddenly flirtation was back in the air, but that unchecked box in my head made the flirtation quickly dissipate into the Manhattan Beach parking lot breeze.

I told her that I was at the stage of my life where the decision to pursue a relationship is influenced equally by what I want, and by what is good for my kids. Her kids were out of the house and in college, and I could tell that she was not prepared for what lay ahead with my pre-teen, boy/girl twins. She had already been through all of that. She agreed with me. This was the unchecked box!

We hugged once more, and stayed in that embrace for a few extra seconds as we inhaled the hint of what physical intimacy would be like. Then we let go, smiled and said a somewhat sad goodbye. I felt a bit deflated at that point, but I told myself that in the future, regardless of attraction and romantic notions, I would try harder not to leave any boxes unchecked.

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