Sheesh, what is it with all these characters having relationships with people that are stalkerish, possessive freaks? Desi Collings, please join Amy Elliott Dunne and Andie Hardy in the Dysfunctional Significant Other Bullpen.
Desi was Amy's boyfriend at prep school, and while things between them went pretty well for about a year, he eventually started creeping her out—"He talked as if they were engaged, he knew the number and gender of their children" (11.126), Nick relates. Yikes.
It's also slightly creepy that Desi's slightly too adoring mom, Jacqueline, looks exactly like Amy. At one time, Amy claimed that after she broke up with Desi, she came back to her dorm to find him naked on her bed after a suicide attempt with pills. She later tells us that she made up the story to garner sympathy from people, but if the story had been real, in this case we wouldn't have been too shocked.
Seeing that Desi was—and still desires to be—Amy's boy, we shouldn't be shocked that he has a "craving for ruined women" (44.18), always ending up in relationships with troubled girls with eating disorders, histories of abuse, and related problems. This is why Amy initially calls him to help her after the Ozark Cabin People rob her blind—she knows he won't be able to resist her sob story.
He's also fabulously rich, and his suggestion of having Amy stay at the lake house fulfills "the ultimate white-knight fantasy: He steals the abuse princess from her squalid circumstances and places her under his gilded protection in a castle that no one can breach but him" (44.62). And, you know, for Amy's purposes it gets her a place to stay where no one can bother her.
Desi's "ultimate white-knight fantasy" is pretty close to what actually happens. When Amy gets to his house, it's obvious that he's been planning for awhile to bring her there—he's painted her would-be bedroom her favorite color and even built a greenhouse where tulips, the flower she loved in high school, will bloom year round. It's "'Your fairy tale,'" Desi tells her. "'I want you to see what life can be like'" (46.21). Hate to break it to you Desi, but this is more like a nightmare than a dream come true from where we're sitting.
Every girl might want her own Prince Charming, but Desi's more like Prince Creepy—especially after he refuses to let Amy leave the house for almost a month. Coupled with the fact that he's apparently had these rooms ready for Amy for months—maybe even years—and it's all kind of Jay Gatsby-ish when you think about it. You know—preparing a fabulously expensive house just to impress a chick. Desi's just a bit darker about the whole thing.
So at the end of the day, what do we make of Prince Creepy? He's probably one of the most ambiguous characters in the book. On one hand, he's overprotective and possessive and seems to have serious mommy issues, but on the other hand, Amy kind of kills him and pins her kidnapping on him, so we feel sort of bad for him despite said creepiness. She might say he raped and abused her, but that doesn't make it true, or even mean that he had bad intentions in keeping her there.
And this, we think, may be Flynn's point exactly with Desi's character: Because of Amy, the records will portray Desi as a criminal, and although we know the truth, we still regard him with suspicion. Amy's just that good at what she does.