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Unexpected lessons from a book on dating


About a week ago, I was struggling with what I saw as typical inaction when it came to getting to know women that I might be interested in. Whether its at the grocery store and someone catches my eye or out at a bar the thought is always, "what do I do?" And with great consistency if I may say, my response is almost always nothing. What else did I need to know from a knowledge or inspiration side to step up to the plate?

After searching around the interwebs for a bit, I decided to try The Dating Playbook for Men. With a title like that sleaze is likely the first thing that comes to mind. But what I've found thus far is intriguing and unexpected. Two observations:

  1. The first two chapters (of seven), have little to do with dating. Instead they cover: knowing who you are, what you value in life and acknowledging your life is great now as it is. Dating, relationships and love are great but the author drives home that if you can't be happy on your own, you almost certainly never will be a couple. As a yoga practitioner, I must say much of what the author writes, would fit well in a yoga class.

  2. The second chapter is about mindset. After exploring personal values and self-worth, the author encourages the reader to feel good about those things before and while you approach someone. You are a good person looking to meet other good people. You are a good human being that believes in creating value for others (plutonic and romantic) and thus put yourself out there regularly to find people worth meeting. When I read this chapter, it was easy to draw a corollary to business networking events. In such settings, I often hold back on walking up to people and rather wait to be introduced or have a specific reason to approach because I second-guess my worth. But if I choose to see myself as a professional with purpose and value, "why would't I walk up to people at the event?" We might find something interesting to discuss, a connection we should make or even a cause to do business. If I approach with those intentions, why would anyone be insulted or feel bothered?

After that is when the book moves into a more focused discussion around approaching women authentically and committing to the fact you're going to fail often. They're not looking for anyone to chat with, they're already with someone else or you're just not the right fit. But if you wait for the perfect moment to jump in - which rarely happens - you're never likely to know at all. A woman I'd find interesting conversation and chemistry with might be in the room I'm in right now but if I don't take action, I will never know. So it is important to take action from the position and mindset of being a good, fun and confident person who takes risks and then allows the chips fall where they may. It reminds me a lot of an entrepreneur pitching a customer or investor. You won't know if someone is interested in your business until you speak with them about it. You will learn far less by guessing if they're interested or waiting for their attention rather than by giving it a go.

The girl I see at the bar, the park, the grocery store or charity function probably isn't interested or available. But how will I know unless I try? And if I try in a way that is non-threatening, respectful, fun, and grounded, am I doing harm? The answer in almost every case will be 'probably not'. There may be a couple bizarre stories but on a number of occasions I will at least find myself in the middle of fun conversations and I can take solace in knowing that I put myself out there and didn't let the right opportunity pass me by.

Here is to the adventure and working hard to be myself and share that with others.

Go Forth Boldly


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