Jessica's Attempt to Win Someone's Heart: A Short Story

I used to love this one boy. I mean, really love him. So much that I was willing to push aside my natural tendency to treat all boys like "buddies," especially boys that I Like. (It's a defense mechanism because I'm lame.) I was determined to win this boy's heart, so after establishing a friendship, I began to take measures some might classify as a little desperate to try and get him to date me.

I wrote him a love poem. One of the lines in the poem stated that he had "the cutest derriere." (For those of you who don't know what that is, it's his butt. He didn't know what it meant either, which made what should have been a cute moment really awkward.) The poem won his laughter, but not his heart.

I invited him over to my empty apartment to watch a show we mutually enjoyed. I turned the lights down and wore my best lip gloss and glanced at him flirtatiously all throughout the show. I think he thought I had a fever or something.

I asked him on a date. I did so by writing my invite on a very long, VERY thin piece of paper, then wrapping that paper around the wheel of a dental-floss container that I had dissected. He read my message by pulling it out of the floss slot. He came on the date, and it was fun, but still no sparks.

I enlisted the help of my boy-crazy and bold roommate, Emily, to help me capture his attention. We all went out one night, and Emily succeeded in getting the boy to sit in the front seat of the car with me and she even planted the idea of he and I dating in the conversation in almost a subtle way. Just when I started to feel those wonderful butterflies that often signal MUTUAL attraction exists, my dear roommate asked the boy if lesbians turned him on and why. It killed the mood and the butterflies.

After all this, I probably should have just gotten the hint that He Just Wasn't That Into Me. But I really, really loved him, enough to sacrifice my pride over and over again. I was lamenting to a good friend named Megan one evening about how this boy wasn't coming around, and she convinced me to make one last grand gesture. She reminded me that the way to many boys' hearts is through their stomachs. With her help, I concocted a plan. We would wake up at the crack of dawn to make homemade cinnamon rolls. (Those of you who know my aversion to early mornings will recognize what a sacrifice this took on my part.) We would take the still-hot-from-the-oven pastries to his apartment, wake him from his slumber and then let the mixture of their deliciousness and my awesomeness finally open his eyes to his undeniable love for me and then he and I would live Happily Ever After.

The plan started off ok. I didn't wake up quite in time, so Megan (because she was so wonderful) started the cinnamon rolls without me. She accompanied me to the apartment complex where the boy lived and sent me to his door after bolstering my confidence that this plan was SURE to work! I excitedly marched up to his door, balanced the plate of cinnamon rolls on one arm, and rang his doorbell. Then I waited in giddy anticipation. A (long) minute passed...and nothing. I let out the breath I had been holding and rang the doorbell again, this time accompanied by a knock. ... still nothing. One last try, then I waited with my heart pounding and the steam from the cinnamon rolls wafting around me. Still nothing.

All that planning, and he wasn't even there to answer the door! I sadly tried to decide what to do. Should I come back that afternoon and give him the cold, but still delicious cinnamon rolls? Should I leave them on his doorstep with a note?

I probably should have done either one of those. Instead, I took the cinnamon rolls with me back to Megan's car and we took them to a friend's apartment and I ate most of them myself. (This type of reaction is why I'm chubby AND why I'm still single.)

My quest for the boy's heart ended that day. I drowned all my sorrows in a pan of cinnamon rolls and a tall glass of cold milk and then moved on. I guess an ending in which my grand gesture prompted exactly the reaction I wanted would have been nice, but it sure wouldn't have been as entertaining!