I have been online dating this round for about 4-5 months and my approach has drastically changed during that time.
I used to have a list of ‘must haves’ and ‘deal breakers.’
I felt it was very important to keep track of the ‘checklist.’ It is so easy for me to go with what feels right at the moment, without considering major holes and red flags. (Been there, done that in both of my long term relationships over 30 years).
But I realized this checklist approach was way too formulaic, keeping me- and my date- from truly being present and open.
There was no real space for the actual date. It was taken over by the noise of each of our hidden checklists ticking loudly in the hidden background.
Almost everyone says in their profile that kindness is the most important trait in a partner or in themselves. But are we kind during first dates? Or are we too busy assessing, evaluating, judging, crossing off, etc.?
We are trying to find our person. We are putting ourselves in a vulnerable position to be rejected. We are trying to reveal our authentic selves. We are searching for someone we can love and care for and be loved and cared for by. This is no small feat. We need compassion for ourselves and each other.
So my approach has evolved. Unless its a hard ‘no’ in my gut, I now go on a second date with most people, assuming they are interested.
Which reminds me. Not everyone is interested. In fact, I have been rejected by two men after the first date, about a month apart.
In both cases we had had a very stimulating, intellectual conversation that was strictly cerebral, despite my best efforts to pivot to a more personal realm. I can still hear the tight tone of each of their voices. I could almost see the cogs and wheels in their brains turning, judging, measuring, and quantifying.
At the conclusion of each date, they each physically backed off from me, although they each had given me a hug hello. This was a pretty clear indication of what was coming.
Indeed, within an hour or two, I received a text from each saying said they enjoyed the conversation, but didn’t feel there was a romantic connection.
I would have gone out on the second date with both of them. There was no hard ‘no’ inside me. I have had many ‘meh’ first dates where the second dates were much more open, comfortable, and personal. But they were in binary mode and it was a thumbs down. I get it.
Statistically the likelihood of a better second date with either of them was slim. But still, I have been surprised before. Generally, I find second dates to be so much better than first dates. Each of us is more relaxed and comfortable.
I met one man who has gone out on two dates a week for three years and has only had one short-lived three-month relationship in that time. I met another man who has been doing online dating for 15 years and is not giving up.
I have had six dates now with someone with whom our first date was nice, but without obvious pizzazz. He is a lot shorter than most of the men I go out with and we are not a likely fit. But I really like his delightful energy and we have a good connection. Every date reveals new sides of ourselves as we converse for hours at a time.
I like how I feel around him. Each date we grow closer and enjoy each other more. It feels promising and full of ease. I like the sound of his voice, his twinkling eyes, and his unassuming confidence.
Instead of interviewing him with my checklist held tight, I tried to create a nice space for our first date — one that was open and kind, and he was very responsive. With that kind of soft space and unrushed time, our connection has blossomed. Sometimes before I see him again I wonder if there is a connection, and then I see him and it’s absolutely there and growing. I am so grateful we both kept showing up.
I am getting good practice in this new approach in my dating adventures. Whenever an intrusive desire to resort to my checklist announces itself, I just relax and return to the present moment. I think about the kindness people say they value in their online profiles and try to apply it right then and there.
It may be a subtle shift, but for me it has made all the difference. I have gone from asking a lot of background questions, i.e. childhood, relationship history, work, etc., to just talking about anything and everything and to feeling out the space. Do I enjoy this person’s energy? Can we connect? Is the energy between us good?
The second date helps me to feel out whether to go forward for a third date or stop. Because this dating stuff is an art and not a science. Our hearts are tender and delicate.
I recently rejected someone after the second date. The first date had been kind of fun with many similar interests and values. We found a compassionate space pretty easily. But the second date made it pretty clear that there was not enough energy or connection to continue. It’s never great to be rejected — nor is it fun to reject — but I really try to make sure gentleness and civility are present.
I had a second date with someone else recently. I was not very excited about the first date, but he asked me out again. With the absence of an internal hard ‘no,’ I said yes. Unlike the first date, we laughed almost the entire time. We had a delightful and slightly outrageous conversation in comparison to the he first time which was stiff and cerebral. I was glad I didn’t miss that second date. Unfortunately, the third date left me with a very clear and loud hard ‘no’ feeling, so there was that.
Instead of feeling like some kind of determination has to happen by date three, I typically wait until date five or six. And very often, even if a romantic relationship does not appear to be in the cards, an enduring friendship does. I have made some amazing friend that I cherish.
So, if you are looking for your person in the online dating realm, here are my top suggestions:
Let go of the checklist, and just come from the heart when you meet someone in real life for the first date. Have a conversation without an agenda.
Unless your gut says ‘no,’ go on a second date even if the first date was ‘meh,’ just to treat the dating space kindly and generously. The second date may be a lot more comfortable and relaxed and fun. If nothing else, it’s great practice in relating and conversing and leaning in.
If you make it past the second date, give yourself as much time as possible to feel out the potential of the connection with this new person to grow and build something real and good and loving.
And most importantly: Approach all dates with compassion for yourself and your date — and all of us valiant daters — who keep showing up and trying to find our person!
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Previously Published on Medium
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