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Sexual prowess and masculinity are often closely intertwined. We see it in literature (like Love in the Time of Cholera) and in films (umm, Deuce Bigelow: Male Gigolo?)—and we see it in Everything is Illuminated. Alex, who is Ukrainian, also believes that it's important to be sexually promiscuous in order to be seen as masculine. This must run deep in the culture, because in the story Jonathan crafts about his Grandfather, Safran sleeps with pretty much everyone who moves. It must skip a generation (or two), though: the sexiest thing we see Jonathan do is peer down a waitress's blouse.
Alex thinks that being sexually promiscuous makes him a more "premium" person; however, he ironically thinks that Safran should settle down and love just one woman. At heart, he believes in love more than sex.
In Everything is Illuminated, love matters more than sex. That's why Safran can't orgasm during sex—he doesn't love anyone he has sex with.