Warning: A whole lot of navel-gazing follows. This is, to paraphrase my friend Jon, your front-row seat to my psychotherapy. If you don’t want to be witness to that, c’mon back another time.

I was seeing someone for a couple of months and we broke up a couple of weeks ago.

This likely comes as a surprise to some of you. Not that I broke up with someone — that’s happened in every single relationship thus far in my 51 years; it’s such a common occurrence now that my buddy Dave just sing-songs every time it happens, “Another one bites the dust” — but rather that I was seeing someone. That might have been surprising. We were only about two months in so we hadn’t done enough to where my relationship status was visible, on Facebook or, you know, in real life. But yeah, I was dating someone and it was good.

But going through another (apparently inevitable) break-up leads me to the question: What the hell is wrong with me?!

She and I met this summer when we were both participants in our local bicycle shop’s weekly group ride. In this era of online dating, it was especially awesome to meet someone organically and to hit it off right away. I’ve been online dating for so long now — going back to the days when my company, Citysearch, was under the same IAC umbrella with Match.com — that I can’t remember the last time I dated someone I’d met in everyday life.

So this was particularly exciting. And maybe that was part of the problem: I set my expectations too high. But part of the problem was definitely timing: I was so of the mind that I was in some fashion taking off to travel after the summer ended that when my dream of a sailboat began to take concrete shape, I went so all-in on making that dream happen that I didn’t invest enough in the potential relationship that was taking shape at the same time. For that lack of investment I’m sorry. But I’m not sorry that I invested in the pursuit of my dream.

And that’s why this failure of mine has prompted in me the questioning of why, when I dream, is it never of a happy, successful relationship but rather of another “thing” on my to-do list?

In 2004, I opted for my dream of a life in Alaska over a truly great love. It wasn’t a simple relationship-or-Alaska quandary; there were other factors, of course. But at its simplest level, do I regret that choice? I don’t know. I always say that while I might have done some things differently in my life, I don’t do regrets because my life as it has been constituted thus far has shaped what I feel has become a pretty good, pretty fun life. But as good and fun as it is, there’s still a huge hole in it. And while to this day I am deeply saddened at the ending of that relationship, I am deeply pleased I went to Alaska. I got so much out of my time in the Great Land that achieving that lifelong dream — even though I was in the city in Anchorage and not out in a cabin in the Bush — is one of the greatest satisfactions of my life, something I’ll take to my grave. But I sure would have liked to have taken that relationship with me as well.

And there have been others. In 2011, I chose to sail the extreme North Atlantic over what was shaping up to be a great relationship in Alaska. I could (the therapist would say “should”) have relocated with the woman I lived with in 2005 as her career went gangbusters. And way back in 1996 I chose to stay in Montana rather than return to Utah and make an effort to save what might have been the great relationship of my life. Again, do I regret those choices? No. And yes.

So now another relationship has come to an end. And it’s not a case of forgetting the past and having to relive it. I’m in full grasp of my abysmal track record when it comes to relationships. That track record has me wondering if I’m just incapable of being in love, of being involved with someone. If so, boy oh boy, that’s a shitty way to go through life. And if not, why do I keep failing at so important a part of life?

In the eulogy I did when my mother passed I described myself as “an emotional cripple.” I repeated that assertion in the therapy I finally got into several months later. After a few sessions, the therapist refuted my assertion and said instead that I’d never had relationships properly modeled for me. I won’t go into the details of his theory and while I appreciate the pass he gave me, I’m not buying the excuse. I’ve had too many opportunities to make a relationship work and I’m still 0-for. And that, to put it bluntly, sucks.

So what am I going to do about all this? I don’t know. I really don’t know. I’ll keep self-analyzing, I know that. And hopefully I’ll find some kernel inside of me that leads me to find a feeling of love for another human being, a feeling that inspires me to open myself and my heart so that loving that other person becomes the top dream on my list and we live happily ever after.

Yes, the fairy-tale ending. Hopefully it’s not too late for me. Through it all, I remain a romantic at heart. Ever hopeful.