What fears/insecurities would stop single men from asking out a single woman they wanted a relationship with?

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I think most guys end up building something like a business plan once they get serious about finding a relationship. My old roommate built a “sales funnel” using Tinder as his “lead generator.” His primary goal is to get girls he’s attracted to into bed, and then once he’s done that he shoots for a relationship. He’s successful at the first goal but not necessarily the second. But generally there’s no room left over in his method for approaching women. They all come through the app.

I personally have found that approaching women out of context, like, say, at the gym or the grocery store, just does not work very well at all. You just don’t get a lot of time to build a connection on that initial meet and if you just ask for digits, even if you get them, good luck getting them on the phone.

I made a connection with a lady at a work happy hour a few weeks ago. She made a big show out of putting her number in my phone and all of that. We talked for like two hours, then I had to go. Tried texting later, nothing. Women simply don’t act predictably enough for random approaches to get anywhere unless you make a lot of them. Even warm approaches usually don’t get anywhere. I’m not afraid to approach women but I have to be in a certain mood before I’ll think to do it.

If you already know the girl, that almost makes it tougher. Asking a girl out isn’t really ‘free’, you can’t just go back to the way things were before you asked them out. If you’ve known them a long time, forget it.

Personally for me, I get a lot more out of it when I let the lady choose her pace. IMO, dating culture is in the process of shifting from guys making all the moves to ladies controlling the direction. I used to think that if I wanted to get anywhere with a girl, I had to make a move. I’ve mostly moved to, “if she’s into me, she’ll let me know.” Anything else seems to get perceived as me trying to be controlling.

My understanding from all this is that attractive, desirable women just aren’t relationship-minded at this time. They might say they are, but their actions indicate otherwise. Maybe the culture will change in a few years or so, but right now this is where we’re at.

I think I know a great way for you to meet guys. Go to a neighborhood bar, alone, during happy hour and stay until around 8 or 9. You’ll draw the barflies, but if you shut them down and stay unattached, eventually the eligible bachelors you want to meet will say something to you. All you’ll have to do is reel them in.