For just a buck, you get the name and number of your one true soul mate. For five bucks, you get your top five. (8.3)
People often have high expectations for Valentine's Day. Like the parties we talk about in "Setting," there's a lot of potential for disappointment if our expectations aren't met. Even if we don't have big dreams for the day, we don't want anything thing bad to happen. Things just hurt worse on a day that's supposed to be all about love.
The valentines are actually more symbolic to the characters than they are to the readers. For Hannah, the Oh My Dollar Valentines seem to symbolize a Valentine's Day gone terribly wrong. They represent the way things always seem to turn out badly when she puts her heart on the line.
For Clay, as he listens to Hannah's story, the Valentines come to symbolize yet another lost opportunity to connect with her. Unlike Hannah, Clay sees the Valentines as a joke, for entertainment purposes only. He fills his out using the persona of Holden Caulfield,the main character from J.D. Salinger's classic The Catcher In the Rye. He purposely doesn't describe Hannah when he fills out the part of the survey that asks for the kind of person he's looking for.
But as he listens to the tapes, he learns that she described him. If he'd taken the survey seriously, they probably would have ended up on each other's lists. He thinks:
If I had been smart, if I had been honest with my survey, I would have described Hannah. And maybe we would have talked. Seriously talked. (8.59)
Ouch. Once again Clay misses his chance. Until he hears Hannah's tapes, he probably never even thinks about those Valentines.