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Val is Moses Herzog's best friend in the whole world—or at least he used to be, back before he ran off with Herzog's wife. Unlike Herzog, Val is a pure extrovert who's confident about his looks and loud with his opinions. As the narrator tells us:
Valentine, furthermore, was exquisitely confident of his appearance. You could see it. He knew he was a terribly handsome man. He expected women—all women—to be mad about him. (1.121)
Herzog will never have Val's kind of bold confidence, which makes it all the harder for him to realize that Madeleine loves Val more than him.
In some sense, Val sounds like an okay guy. But it's hard to forgive him for lying to Herzog's face while he was having an affair with Madeleine. When things go south in Herzog's marriage, Val manages to give him relationship advice with a straight face, saying tender things like,
"You and she—it's no secret from anybody—are the two people I love most." (2.215)
And Herzog is totally charmed by Val's words even in the worst of times, thinking,
He spoke of death majestically—there was no other word for it—his eyes amazingly spirited, large, rich, keen, or, though Herzog, like the broth of his soul, hot and shining. (2.238)
This is where Herzog's masochism comes in: he's obsessed with how hot, dashing and charming Val is, especially when compared to him. He does the 1960s equivalent of Facebook stalking an ex's new significant other… except that he compulsively scrolls through memories of Val rather than pictures of him.