It was another moment of romantic desperation.

I can’t remember what brought it on. Maybe it was yet another conversation with a friend about how horrid the dating scene seems? Or exposure to someone in a seemingly happy, functioning relationship and I thought, “Why can’t I have that?” Maybe it was someone’s wedding photos? Whatever it was, it turned me into a giant mushball of seeming desperation.

I wanted to get married. I wanted to have a kid. I wanted to be in love.

Or did I?

Since one of my friends is a professional matchmaker (you probably know him as “The Modern-Day Matchmaker,” life coach and TV personality Paul Carrick Brunson), I decided to go, “Hey, let me just ask him for advice!” And so I did.

Paul makes an excellent point – both in person and in his book – that you don’t know really how you feel about dating until you actually start to apply yourself to the real work of finding a partner. For me, he suggested branching out of my intimate, immediate circle of friends and going for secondary and tertiary friends I didn’t see as often in order to meet people outside of my circle who could, in turn, become potential mates.

As he was talking, I thought this was a great idea that became less and less sounding like a great idea as I thought about all the other things I’d rather do that go hang out with people and try to meet strangers who I may or may not be interested in. After all, I had a much neglected book to write and a much neglected web site to work on and I had freelance assignments to attend to. Basically everything sounded more interesting than doing what Paul had advised me to even though it was pretty good advice.

In essence, he was telling me you can’t win the game if you don’t play. And here I was, decidedly sitting on the sidelines watching HBO Go and trying to find new exciting recipes for my elaborate dinners for one. Find a man? Sure, I wanted a man. But I didn’t want to “look” for one. Why couldn’t things just happen like they did for my dad, like my future spouse simply showing up at my front door one day?

(Seriously. That’s how my parents met. My mom showed up at my father’s apartment with a friend and now they’ve been together for more than 40 years. If only we all could be so lucky.)

But that’s not realistic. Realistically, you have to get out there and meet people and I wasn’t. And I knew better. That’s not how I live the rest of my life.

“You have to play to win” is the rule I’ve applied to my education, my career, my happiness. I believe that you can’t get where you want to go in life if you’re not willing to be a full participant. To deal with the ups and downs. To take in all the setbacks and complexities, ridiculousness, pain and pleasure. And so I’ve attacked life with a certain ferocity, never afraid of a risk or a change, trying something new or potentially failing. Move cross country? Not a problem. Start my career over from scratch? I’ve done it twice now. Take a leap of faith and invest in myself? I’m all for it because I know I will not let myself down. My ego is too big. My heart is too strong. I’ll battle through and rally back from any challenge.

Except when it comes to one thing.

I really stink at dating.

It would be easy to blame my lack of a date on “society”  or how there are “no good men out there” or whatever clichéd thing people say when they don’t date, but the reality is, I stink at dating because of me and only me. Because unlike my education, career and happiness, I’m not willing to put in the work. Unlike with those things, I’m too afraid of failure.

Naturally I didn’t come to this revelation the first five, ten or fifteen times I tried “getting back out there.” For the last five years, I sincerely thought I wanted to meet someone. I would create online dating profiles, go to events, network with people, but the same thing seemed to come up every time. I’d reach out, I’d start talking to folks, sometimes I even exchanged phone numbers or scheduled a date. But I would run into the same brick wall each time. The things they had to say would annoy me, the little jokes or the poorly written poetry. Or sometimes, they did nothing to annoy me at all, I’d simply forget to write back or follow through and respond. Dates would be planned, but I would cancel them. Requests for attention would go without reply. And then months would go by without me checking up on the dating site.

The same went for men I met in the real world. Every man I found myself the most attracted to were the ones most likely to either not be interested or not be available. At first I thought I was just unlucky. Obviously all the good ones were taken, like there’d been some “Awesome Guys to Date” sale and I was a day late and many, many dollars short. But I knew, in my heart, that couldn’t be the case. And, of course, I did have that little problem of the men who were the most interested in me were all ones I didn’t necessarily want. Most were nice enough. Others not-so-nice. But nothing that ever made it seem worth taking the risk and putting myself out there emotionally.

And that was ultimately the issue.

I could see the great “risk versus reward” in every part of my life except romantic relationships because in those relationships you have to give up a certain amount of control. You have to trust. You have to give a part of yourself and you have to open up in a way that I didn’t have to open up for anything else. And while I’d easily bounced back from crappy, dysfunctional friendships, nightmare workplaces and the horror that was public school in St. Louis County, my previous experiences with serious romantic relationships revolved around divorce and a mental breakdown. Sure, I was sad when things didn’t work out in other facets of my life, but when things didn’t work out in my love life I was completely paralyzed and devastated. It didn’t seem worth it unless I was getting into something I was sure I wanted.

And I’ll be honest, I don’t know how “sure”  I am that I want a relationship like how I was “sure” about my career.

Now, I know that not all dating relationships have to be serious, so you could argue I’ve been dating, non-seriously, random guys for whom I have inconsistent interest in, for about six years now. But after talking to Paul and forgetting I had an OKCupid profile for about the fifth time in so many years I realize that, right now, I don’t actually want to be in a relationship. Or, rather I should say, I don’t want to do the work that it takes to find a good relationship. I don’t want to go out on first dates. I don’t want to “try.” I’m in no rush to make new friends and go through all that work of hunting through those new friends for even more people to date. But ultimately, if my goal is to eventually settle down, I have to get back in the game I’ve so far avoided for many, many years. So, there’s a good chance I will take Paul’s advice … eventually.

Like maybe next week. Or next month. Or next year. I mean, I’ll eventually do it. But I’m owning my ambivalence this time around. My being single is no one’s fault but my own.

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