Character Analysis
As you know, Oscar is obsessed with women. And until he meets Ybón, noneof them really reciprocate his interest. Except for his cute little childhood girlfriends. We've grouped all of Oscar's main crushes together here for your reading pleasure.
Jenni
Like a normal college kid looking for love, Oscar meets Jenni at Rutgers. As Yunior says, she was the "first hardcore goth I'd ever met—in 1990 us n*****s were having trouble wrapping our heads around goths, period—but a Puerto Rican goth, that was as strange to us as a black Nazi" (1.4.1.96). Jenni is really hot, too.
Even Yunior seems interested in her. But as is suggested by her nickname, La Jabesse, there's something devilish about Jenni.
You can guess what happens. Oscar begins to fall for her. They hang out together more, even go to the movies. Oscar starts ironing his shirts and jogging to stay fit. In the end, Oscar gets his heart broken when he finds Jenni in bed with a "tall punk kid" (1.4.1.118).
Then, Oscar goes a little crazy. In fact, La Jablesse is the one who sends Oscar over the edge. He tries to commit suicide not long after he finds her in bed with someone else.
We wish we could say that girls like Jenni are rare in Wao. They're not. Oscar has a knack for latching on to girls he adores but who treat him, at best, like a friend. Jenni may be the most extreme example, though.
Jenni's nickname adds a sense of diabolical intent to her relationship with Oscar. It makes us wonder if all of the other women in the novel lure Oscar to self-destruction.
Ana Obregón
Oscar meets Ana in an SAT prep class, of all places. She's Oscar's first real-life girl obsession. Why? She's hot, confident, funny, and irreverent, of course. When she reaches the Elizabeth exit off the highway in New Jersey, which smells terrible because of the industrial waste, Ana screams, "Elizabeth! [...]. Close your f***ing legs!" (1.1.5.30).
Ana also wears sexy underwear and is meticulous about her makeup. She's a little heavy but is super comfortable in her own skin. She even reads erotic books.
But she's kind of a walking contradiction. She strikes Oscar as innocent in some ways, too; she still has a pile of stuffed animals on her bed.
Oscar and Ana get close for a while, but then her ex-boyfriend Manny comes back from his stint in the army. By this point, Oscar is in way too deep with Ana. He even considers jumping Manny with his uncle's gun. (Manny does seem sketchy; he dates Ana when she's thirteen and he's twenty-four.)
Ana initiates Oscar into what will be a pattern for most of his (brief) life. He latches onto girls who don't return his affection. These girls usually go back to tough, abusive boyfriends, or to guys who seem cooler than Oscar. Oscar's always getting Friend Zoned.
But with the Ana episode in particular, we also learn the extent of Oscar's loneliness in his rejections. Some people talk about their first loves; Díaz seems to be sharing Oscar's first rejection, to set up this pattern in his life.
Maritza Chacón and Olga Polanco
Would you ever have guessed our man Oscar was a player? Well, he was. When he was, like, in elementary school. Maritza and Olga are Oscar's "golden age" girlfriends—he dates them during the years before he turned into a nerd (1.1.1.1).
Maritza hangs out with Lola and is prissy and pretty. Olga comes from the poorer end of the block, and sometimes smells bad. Oscar dates them both at the same time until Maritza confronts him about the situation. Oscar breaks up with Olga, but then Maritza dumps him anyway.
No one from this love triangle does well in their later years. Olga gains weight and starts drinking rum. Maritza takes up with scary dudes who like to hit her. And Oscar... well, you know how that story ends.