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I don't think dating multiple girls really gives you "experience" everyone enjoys different things and acts different in relationships, you can never understand women and it is a scientific fact.
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It totally does. There's no way anyone is completely comfortable on their first date ever, or first relationship for that matter. Especially if you are an awkward/shy person, then you really need the experience of going on more dates so it can become a normal thing for you and won't be terrifying or difficult. And if you have trouble "understanding" a woman then generally that means a lack of communication, or not being very honest with eachother, or you may be socially disabled.