JESS: Find someone who vaguely resembles me. Take him. Just don’t kiss him goodnight.
RORY: That’s not going to work.
JESS: Andy Warhol did it all the time.
Andy Warhol, born Andrew Warhola Jr (1928-1987), artist, film director, and producer who was a leading figure in the art movement known as Pop Art. His works explore the relationship between artistic expression, advertising, and celebrity culture that flourished by the 1960s, and span a variety of media.
I’m not completely sure what Jess is referring to here, except that Andy Warhol did have something of a “type” when it came to his lovers and muses, both male and female. If anyone has any more specific ideas, please write in!
The Annotated Gilmore Girls 
I think he’s referring to the practice of gay men bringing female dates, or “beards”, to functions while still in the closet to ward off rumors. It was a more common practice when the consequences for homosexuality in the West were more serious.
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That doesn’t really tally with Andy Warhol, who was open about his sexuality. When he did date women, it was because he wanted to, not as some sort of cover. Whether Jess understands this is uncertain though.
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“In 1967, when Andy Warhol hired the actor Allen Midgette to impersonate him on a lecture tour of America, he effectuated one of the great Dadaist acts of the twentieth century.” Source: http://www.Gagosian.com
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