When I lived in Medellin in 2016-2017, I met several men I liked. I kept them in my “maybe-dating limbo land.”

When it comes to high-stakes / high-commitment stuff, sometimes I can be more comfortable keeping possibilities open, instead of addressing them. Maybe I’m afraid to find out an idea is a failure, whether for my long-term career or for a potential relationship. Because failure implies fewer open options. And that sounds bad. Keeping ideas in my limbo land is a comfort zone, because it feels more abundant. But I know it isn’t actually, and as I’ve seen, it doesn’t yield results.

So with my new 30d30d perspective, I see life as an opportunity to retake serious looks at former crushes, make yay/nay rulings, and move on. In the case of yay’s, I consider myself required to make a move. Here in Medellin again, concurrent with the Saga of Henry, 3 guys occupy my mind:

• First, there is my trainer George. Tall, fun, flirt, easy going. It is easy to develop a close physical comfort with your trainer, so they say. You tend to trust them a lot — from fitness plan design, to your very life when you’re lifting heavy weights and they’re your fail safe. I experienced such closeness and trust with George, even when we first met in Salt Lake. He pushed me like other trainers didn’t. He also coined a phrase I always try to keep alive: “sweetie, you need to stay open — open eyes, open mind, open heart.”
• Second is Frank, the owner of a local adventure tour company. My age, fun, fit, dynamic, entrepreneurial guy from the barrio. Spoke zero English, and had developed a very successful company. I went on many of his tours back in 2016. We had started getting lunches together, often ending with a motorcycle ride. I loved sharing our cultures, and the challenge of bonding in a foreign language. Very independent guy.
• Third, an engineer, Eric, who I had met at a coworking space. Somehow, his background and interests and ideas were so closely aligned to mine. We had long, interesting conversations about all aspects of life. He like cycling too, and in 2016 we did a couple of rides together. He was a bit of a flake as a friend, but when he was present I loved our time together. In 2016 I had told him I had feelings for him, but he was interested in someone else at the time. We remained friends.

Now back in Medellin, one by one, I’ve spent time with each of the three. The result: I realized each match wasn’t quite right. And I was able to let them go.

My trainer George’s attention was quickly diverted — specifically, to a younger friend I started bringing to training sessions with me. When his attention towards me diminished, so did his effectiveness as my trainer. Sigh! He also had a business idea that he wanted me to help him with, but his manner of pitching it and then dictating his plans for “our” business wasn’t compatible with my notion of collaboration and partnerships. I concluded we wouldn’t make terribly good partners. Still, George remains the best trainer I’ve ever trained with, and I gladly keep him as a caring friend.

Frank the entrepreneur was very independent indeed. I came to see we simply want different things in life. We met for lunch at one of my favorite spots — ‘Cafe Revolucion‘ owned by a cute, friendly, muscular, tattooed neighborhood Hungarian. Frank and I were very open with each other, even more so than before. He was quite flattering in telling me some of the things he loves most about me — my spirit, my openness, my ability to say yes to new things, my adventurousness. I really appreciated hearing this from him, and knowing that this part of me shines even in my nonnative Spanish. The language barrier got in the way a bit, but my Spanish was improved since 2016. Still, his dream future was to live isolated on a wild beach at the border to Panama, and to focus on his business. Mine is to be surrounded by community and nature and life, probably in the Northern Hemisphere, and use my career to help people. I really enjoyed his company though, and have a lot of respect for him as a friend.

Eric the engineer had gone through a long and complicated relationship history since 2016. He was newly single, and his life was complex. I went to visit him at his new apartment. It was great to see the inner side of him and play with his cats. But as we talked more, I noticed for the first time that our world views didn’t really match. Any desperation I had formerly felt for wanting to be with him started to melt away. I saw incompatibility; I also think I saw us the same way he sees us. We did do another long (and excruciatingly hard) bike ride together though!

Those were the main ones, but there were a couple others. One by one, I saw that by being open to evaluate a person’s compatibility to me, and let the idea either succeed or fail (without any judgment falling to either of us), I no longer felt a strong controlling urge to hold them in my “maybe limbo land.”

In love, like with startups, I’ve learned it’s best to ‘fail fast, fail early, fail often.’ It may feel uncomfortable at first, but it’s actually liberating, and it makes more space for better fits. The desperation to have potential options melts away, replaced by a desire to form new bonds.

I love this new approach. With a bit of luck, I’m confident that new people will enter my orbit to replace the old ideas.