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When Everything Goes Right: Do You Have a Dating Roadmap?

What does it look like when you are happy? What are you doing?

Not to mirror my current situation (idle and a bit bored with the online dating app world) I’ve been thinking about what it would be like to find the perfect fit. Do you know what your best-case scenario looks like? If things go exceedingly well… How does that play out in your mind?

Robert Grudin, in his fantastic book, Time and the Art of Living, has given us a model for looking at all three modes of time as valuable teachers. Today, we’re so focused on staying in the present moment, we might miss the other two modes. In fact, some would suggest we need to avoid putting any energy and time into the past or the future. Grudin suggests that there is value in contemplating all three modes.

Future time is the contemplation of things as you see they might happen. For some, this becomes worry about what is essentially uncontrollable by us mere mortals. In Grudin’s mind, dreaming about the future can give us a lot of joy, and inform some of our decisions as we adjust to aim our lives more towards that envisioned future. The future we want is only achieved by building and following a map. A spiritual map. A roadmap. A to-do list. We need to know what our intentions are and micro-adjust our lives as we move down the continuous experience of time. We must constantly correct towards our goals. If you don’t know your ultimate goal in starting to date again, you might be disappointed when you don’t achieve much success.

If we go away from our goal, as an example, other information might come to light. I was discussing my dating challenges with a friend the other night and we hit on the topic of younger women. It’s what our culture says is beautiful. It’s what a lot of men in the online dating sphere are hunting for. And… It’s not really for me, or for my friend. He said, “If you imagine things going really well and you are getting close, what’s one of the best things that can happen? I learned in my brief experience, as things progressed, I found myself sitting in a room full of her young friends. I had no one with whom I could relate.”

Are you hunting some imaginary muse of beauty or youth that ultimately will leave you a bit hollow? What are the qualities you are hoping to find in your perfect mate? Are they creatives? (musicians, writers, performers) Are they extroverted and in charge kind of people, so you can sit back and go along for the energizing ride? Is there fitness more indicative of your own commitment to staying in shape? Or have they taken the idea to the extreme? Do they talk about the gym and working out as if it were part of their spiritual journey? (If that’s yours, they might be just what you are looking for.)

For me, I want some kind of balance. I want a person who walks with confidence in whatever they have decided to do as part of their life work. I can even support someone who is still seeking their lifework or purpose. But deep spiritual values and strong ambition towards some self-actualized goal is a must. I need to see my partner as a friend on the path. (See: Friends on the Path) It’s not about church, it’s not about Jesus or God. I believe in a more Jungian model, it’s about a spiritual connection to some higher power. (More Jungian supra-consciousness rather than the 12-steps, but I like the 12-steps a lot as well.)

The beautiful woman at the bar who catches my eye is not really meant for me. Someone 10 or 15 years younger than me, is going to be working on very different life goals, I think. This imaginary youthful beauty is thinking about a career, maybe still about children, about how to make ends meet. These are all valid pursuits, but not exactly in line with things that are most important to me. I have two kids. I have succeeded somewhat in my career and am looking to pivot towards doing more service work. I have figured out how to earn a living (walk the Earth) with intention and conscious direction. I do, sort of, know where I’m going.

So, now the harder part: What does my best-case relationship look like?

Rather than a bullet list, I’m going to address a few of the bigger areas of connection that I seek and see how close that gets me to my map.

Creative vs. Grounded

I’ve been struggling with this one a bit lately. Do I need another artist to be in love with? Is supporting their creative endeavors part of what connects me with a partner? (It did not work in my first marriage, was a bit more successful in my second.) Or, do I need someone who is happily finding their way as a good and loving human being? Working in their career, doing their job, planning for retirement and vacations in a methodical and calculated way. I framed this concept in my mind as, “Do I need another rock star, or would a terrestrial body be better for me?”

Fit vs. Whatever

I was in a relationship with a marathoner once. Amazing. Perhaps, for me, a bit on the fanatical side. We would discuss every day, “What are you going to do to workout today?” It was a good connection. I took up road biking to find a sport where I could almost keep up with her. We both respected the physical body and took delight in each other’s fitness. I don’t need someone who is uber-fit, but I’d like someone who’s maintained some athleticism. At our age, if you haven’t, it’s hard to pick it back up.

Financially Secure vs. Still Working On It

I am definitely still working on it. I’ve reached a nice balance in my life, at the moment, but I’ve been in relationships where our historical relationship to money has played a counterproductive role. Money is something that has to be mastered in order to move on to higher things. Struggling at a day job you hate is a hard place to be. I’ve done that. I’ve been with someone in that position. In both cases the imbalance caused friction. Get your own money house in order and then see if you can find someone who has their relationship to money figured out as well.

Optimistic vs. Pragmatic

I am driven daily by my optimistic and positive outlook. Sometimes it’s a fault. But I know I need someone who approaches the world in the same way. “What can I do today to make a difference?” Sure, I will sometimes go off on a whim and spend time on a project that doesn’t pan out. But, it was a learning experience. I am definitely looking for an optimist. I am listening for their inner joy. These are qualities that are innate and very hard to change.

Beautiful vs. Pretty

I was about to skip this one altogether, knowing this is a lightning rod subject. But, I would’ve been missing one of my own Achilles heals. I fall too quickly for beautiful women. I can see that I would also be happy with a pretty woman. I have been with pretty women and was quite satisfied. But beauty is a slipping point for me. And, at some level, I don’t trust a woman who is too pretty. I’m afraid she’s going to be weighing her options (since she has so many options) and eventually will choose someone other than me. And yet, I aspire to beauty. I write poems to beauty. I court women on dating apps who are beautiful. But I wonder, am I batting out of my league? Or, does a beautiful woman have a different, somewhat entitled, take on the world? I have not been very successful with beautiful women. I seem to be much happier with women who are pretty but not glamour pretty.

In wrapping up this idea, do you know what your best case relationship looks like? Can you envision the things that you will be doing together? Maybe you should start doing those things now, before you meet the right person, and see if they (this potential date) is also already engaged in this activity. Church, bike riding, rock climbing, live music concerts, whatever it is, get out there and start doing what you’d love to be doing with a partner. Perhaps that’s where they are right now. Maybe not looking for you, but just climbing the rock because it makes them happy.

What does it look like when you are happy? What are you doing? If your best case scenario involves continuing to do that (play tennis, in my case) then perhaps you need to look into participating more. The apps are okay for spreading your reach and resetting your ambition, but you need to be doing your dream first, then the right person might come along beside you on a bike ride and say, “Hello.”

Let’s get back out there and start doing what we love and the lover will follow.


John McElhenney – life coach austin texas
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