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Basically, what I am asking is dating always a huge numbers game?
Yes and no. Yes, it is a numbers game in the sense that you have to practice it and internalize it in order to learn anything. Experience gives you knowledge.
However, no. It's not a numbers game if you are thinking just approach as many women as possible. Sure, that might work a few times for you. More interactions does not mean more sex if they were all shit interactions. Get better each time.
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Are any of you guys so good with your social skills that you can see a hot girl somewhere and pretty much guarantee you can get a date with her (assuming she's not married/ engaged/etc...). What is your general closing percentage when you approach women in terms of getting a date?
No guy on this planet is that "good" that he can pull any woman he wants. It doesn't work like that. These are human beings we are talking about. For starters, there is this little thing called "sexual chemistry" that's important/required between two people having sex. This is not a science dude. Not everyone is gonna like you.
However, learning how to interact with women better does give you the ability to swing things in your favor a little bit. Not 100% obviously. But accept that this is a skill and the more you practice it, the better you will get.
Which brings me to... Don't worry about what your "closing percentage" is. There is no monthly bonus if you have a higher close rate. Go out and talk to girls because its fun.