The art of conversation for a man can be daunting if he believes the woman is physically attractive and "out of his league." That belief is psychosomatic.

What do most really offer besides appealing to the eyes?

Do they have stimulating thoughts and profound character traits that are hard to find?

Can they share something unique about themselves such as their favorite food to cook? Favorite book they've read? Instrument they play?

Do they know their credit score?

Can they talk about current politics and world events? Or are they typically used to being asked their name, just to turn down the guy who's making a failed attempt at her affection?

Do they have fascinating college or grad school memories? Did they even expand their knowledge base beyond a high school diploma?

Do they own a passport? Where have they traveled?

Can they talk about their diversified investment portfolios and its current allocation? Do they even know what a 401k is and the employer's matching percentage?

Do they have their own place, or living with roommates?

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No? Then why they hell do you think they're out of YOUR league?!?!?!

Keep that in perspective and your interactions with the other sex will be very different.