If you surrender to a dating-profile makeover and give a few of these women a better look at who you are and what you have to say, who knows where it might lead
What do you have to offer a partner if you’re already unwilling to share the most basic details about yourself so someone can get a real sense of you? What actually makes you a catch? So far, all I know about you is that you’re employed and you’ve done okay for yourself. Which makes you equal to a decent percentage of the population. Who are you beyond your go-to labels of “private” and “entrepreneur”?
Really think about these questions, Discreet. I’m not messing around, and the ladies aren’t either. Your honest and open 
take on yourself matters, and that info is exactly the kind of thing good women want to know straight out of the gate. Forget about what YOU want in a woman, and start thinking about what you have to give.
That guarantees you’ll be meeting like-minded souls, face to facemunity service is another great route for more reserved people to find each other, with no pretense (or ridiculous sex questions) to harsh your mellow
You built your business by breaking rules. That’s groovy. Has anyone ever told you that building a business is not the best template to use when it comes to forging relationships?
But you didn’t get to be an outstanding entrepreneur by just breaking a lot of rules. I’d venture a guess that-outside of love, maybe-you also possess a modicum of flexibility, good judgment, and the ability to switch gears when one business tactic isn’t working. Are you willing to switch gears to win a shot at meeting someone special?
Because if you’re honestly looking for strong, smart women, it sounds like you’ve already found them: they’re the ones refusing your approach. They’re cautious. They know their limits. They stand up for their boundaries. And that’s smart.
Do you know how bad it is out there for women on dating sites? Take a look at this to get an idea of the hostility and shaming and danger that women face online. Those are real dudes, Discreet, and they are real angry. You may be a harmless-enough chap, but if you really want to be respectful to the women you want to meet, you need to honor the fact that it’s a jungle out there.
I’ve been focusing on the difficulties and very real dating dangers that women face in hopes that you’ll understand better how women feel when a faceless stranger reaches out. But online dating-or any dating, really-is no picnic for straight men either, I know. (My LGBT readers, I don’t presume to know your experience, but I’d love to, so write soon). Now, if you’re still writhing at the thought of completing your dating profile, Discreet, maybe online dating just isn’t for you and never will be. The on-the-ground approach, although also challenging, may actually serve you better. Maybe it’s time to suit up and hit the conference circuit in whatever field your business is in.
You tell me, Discreet. What’s your next move? Are you sure you don’t want to give it the old college try for six months?
I really hope you’ll stay in touch. And I hope that you will take some comfort (and find some humor) in learning that you’re not that special. I say that with great benevolence. NONE of us-not the extroverts, not the introverts, not the ambiverts-are that special, and what a relief that is. Because not being special means this big and wonderful secret: nobody really cares that much about what anyone else is up to because each of us is busy worrying about our own messy, hopelessly hopeful hearts-and how to keep them intact. That’s what I think this privacy thing is all about. You say very little about your divorce, Discreet, but I can’t imagine you went through it unscathed. Love is magic, but heartbreak is lousy.