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It's very frustrating to ask women out and get rejected time and again

It's very frustrating to ask women out and get rejected time and again. How can I lessen the risk of rejection?

Do you have the expectation that every woman you ask out will say yes? No one has 100% success in anything, and dating is certainly no exception to that. The easiest way to deal with the rejection is to live realistically. Not everyone will go out with you. There are women who don't believe Tom Cruise, Denzel Washington, and Brad Pitt are gorgeous or desirable and who wouldn't go out with them on a bet or a dare.
Don't place so much emotional investment in the act of seeking company. Say you're at a party and there are forty women there. Don't focus on that one woman and put all your emotional eggs in that basket. If you do and she says no, the rest of your evening is shot. Instead, look at all forty women with the idea that you're going to speak to all of them. You might find the one person you thought was hot is someone you don't want to spend time with. You might find the one person you would have avoided has a wicked sense of humor and thinks Peyton Manning deserves the MVP.
The point is to take the first step without getting so worked up over it. If someone tells you no, understand that's their right and their loss and move on to the next prospect. You won't lessen the risk of rejection, but you can lessen your reaction to it.
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