I read something today in The Independent about a gentleman who purchased a pair of leather pants at the urging of a woman he wanted very desperately to French, and later sold them on eBay to great critical and public acclaim. Honestly, the outpouring of affection for his eBay ad struck me as a little disproportionate, but many things that wildly spread across the web – including things of my own invention – feel much smaller than the reactions they garner.

But the story reminded me of the ridiculously stupid things I've done to casually earn the attention of some woman or another when I was younger. The earliest example I can remember is when I, in the summer between my junior and senior years in high school, had a tremendous crush on an outgoing senior who was headed off to college in the fall. She worked in a book/greeting card/Gund®/delicate ceramic animal store that failed on pretty much every one of those fronts. (And, not surprisingly, no longer exists. I'm sure there's a mobile phone store in its place now.) I sometimes popped in on my way back from purchasing Cinnamon Softees at the drug store next door. My visits generally lasted for about five minutes, during which I'd thumb through the latest humor books, like Generation Ecch or Son of Sniglets, or one of the many Bloom County anthologies. I wasn't much for reading.

But at the time I was very much for trying to make out with tiny, withdrawn, cynical, slightly older women, and one of those women worked the register during a few weekdays. My crush on her brought me into the store more and more, and significantly changed my browsing habits. Instead of reaching for Billy and the Boingers, I started blankly staring at the three or four rows of "important" fiction classics, desperately hoping she'd notice.

One day I decided the only way I'd summon enough nerve to speak with this girl would be through a completely transactional relationship; I was going to buy something in order to break the ice. (In hindsight, it has occurred to me there were several easier, more honest, and less costly ways to start a conversation with a girl from my high school working behind the counter of a lousy shop. It gets boring back there, and most people welcome interesting small talk, providing the person initiating that small talk isn't fumbling around lustfully in his front jeans pocket.) However, if I were going to do this, I wanted to make sure I dazzled her with a purchase that was not only solid in its literary merit, but also telegraphed itself as slightly offbeat and uncommon. A classic, but not necessarily one we'd had pounded into our skulls in high school. In other words, A Brave New World and Hammer of the Gods were both out of the question, even though each contained many interesting discussion points. ("Do you think that's a comment on the post-Freudian self-prescription of our society?" "Do you think that stuff about the baby shark is true?" etc.) A Clockwork Orange was out as well – nicely masculine but, for the purposes of courtship, the novel might come across as a little too "rapey."

There was also my budget to think about. On the salary of a part-time public library employee, anthologies and hardcovers were strictly out of the question. Finally, I didn't want to seem braggy by dropping an 800-page tome on the counter. That meant my first choice – and a genius one, as far as I was concerned – of The Tin Drum did not make the cut. Nor did The Unbearable Lightness of Being because that would sort of be like passing a note that read, "DO YOU LIKE TO MAKE FUCK?" Plus, I'd never heard of that book. Like I said, I wasn't a big reader.

I settled on Sir Thomas More's Utopia, for reasons that still remain completely unknown to me. I guess it just seemed pretentious enough (SIR Thomas!), short enough (about 112 pages or so), and upbeat enough (Not dystopia – UTOPIA!) to impress upon this woman that A) I enjoy reading and B) I am in pursuit of high ideals, that may include but are not limited to creating an ideal society, and touching you over your bra. The truth was, I knew nothing about this book. I'd heard it lumped into a general discussion about dystopian/utopian texts, and I thought it would be an interesting choice.

I brought the book to the counter, a little too proud of myself. Here is the conversation that followed:

ME: "Y-y-you know this book?"
HER: "Nope."
ME: "Cool."
HER: "That's six twenty three..."
ME: "Oh! I don't n-need a bag." (POINTS FOR ENVIRONMENTAL ACTIVISM!) HER: "Got it. Out of seven...thanks."
ME: "OK. Oh, um...bye. Thanks. Bye."
HER: "..."

We really connected.

[Full disclosure: After growing unnecessarily obsessive about my crush, I made a power-move a few weeks later. Drove to her house and left some flowers for her. Can't say why, exactly. I left my phone number and name, too, and she called me back. Soon after, we spent a long evening of late-night conversation on her living room couch. I kissed her goodbye, quickly, and then she left for college. My senior year started, I met someone just as all people meet someone in their senior year. I never kissed that book/greeting card/Gund/delicate ceramic animal store clerk again, a fact that did not come without a bit of disappointment and backpedaling. Also, I never got past page 14 of Thomas More's Utopia. I hope Utopia turned out well.]

That wasn't the last wasted expenditure I made in the name of crushdom. Just ask my copy of David Gray's "A Century Ends" CD. (Purchased at the polite insistence of the record store clerk I was moon-eyed for and listened to exactly almost once. Doesn't matter; I would have agreed to buy anything, even an album by Stone Temple Pilots or Toad the Wet Sprocket, for that woman.) I still have More's Utopia and, despite many better albums that have ended up in used record bins or on stoop sale blankets, I think I might still have that David Gray album. You can't throw that kind of stuff away; it would be like burning a love letter, written by yourself.