Stop buying drinks for women as a way to break the ice! A woman goes into a bar, and guys buy her drinks all night and then she leaves with her friends without spending a dime. This happens every night. Stop contributing to this stupid method of finding out if a woman is interested in you. If you find there's a mutual interest and you want to take a shot then yeah you can offer her one. Just don't buy her more than one drink! I repeat, STOP buying every woman a drink! It doesn't work often enough to pay off in the end.
Your approach from this day moving forward will change when it comes to women. Do you want to spend the remainder of your life chasing women like you have been? Or, do you want to be the one that women chase? Let me give you a little insight into this theory. You have to first act like you're interested but not really not certain about her. Hell, even tell her that she seems really cool but you're just not too sure about her yet. Please say this in a joking manner and smile.
You want to give her just enough that she's the one wondering if you really think she is girlfriend material. This is what I call flipping it. You want to flip it on her so that you are no longer the one wondering if she is attracted to you but she is. This isn't something that most women aren't used to. If she is attractive, which I hope she is and you haven't been hitting those tequila shots all night, then she has heard it all before. Guys tell her she's beautiful and buy her drinks every night. They throw themselves at her and want to do everything for her and buy all her drinks and talk to her the whole night. Say something that no other guy has said to her. Nothing creepy though. What is the first thing most guys say to a woman. "Hey I'm blah blah blah" "What's your name". LAME. Stop being like everyone else! Go tell her that you and your friend are out tonight because he broke up with his girl last week. Ask her how long he should wait to start dating again. When she gives you her answer laugh and tell her thanks for the opinion. Then walk your ass back to where you came from. If she makes eye contact, smiles at you, positions herself toward you or any other sign then you can get an idea that she may be showing interest in you. If you don't see any of these signs then don't pursue her. If she is interested she will let you know even if she doesn't want to through her body language.
Never, I repeat, never, show any interest until you see signs that she is interested. If you don't follow that golden rule then you might as well shoot yourself in the dick because you've just handed all the power over to them. Whatever you do.... please stop buying drinks! It's not being a "gentleman" it's being stupid. I will cover what being a gentleman is all about at a later time. For now.... remember the golden rule and start flipping it on every woman you come in contact with.
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