The following submission received first runner-up in our Stories of Woe Valentine’s Day Giveaway. Tim’s story will be performed by local improvisers, filmed, and posted on our site in the weeks to come.
High-five for love
Let me set the scene for you. It’s a Sunday. Three girls, three guys – all of us freshmen dorks. We’re sitting outside our dorm marveling at how pitiful we are at attracting members of the opposite sex, when one of us observes that our chances might improve if we were to actually ask someone out. While we together struggle to refute this truth, someone offers a challenge: each of us has to convince a stranger to go on a date the upcoming Friday at El Arroyo. What the heck, we shrug, what’s the worst that could happen?
I set to work the next morning with a fervor borne of prolonged abstinence. I arrived early to my first class, sat in the back, and mentally checked-off classmates as they filed in. There was Cheryl, the lesbian. No good. Kristen, hairy Earth-woman. Yikes. Sienna, Type-A, overachieving, obsessive compulsive hand-raiser. Hell no. Then there was Katie. Blond, athletic, quiet to the point of mysterious. Compared to the others, she looked like Aphrodite. Bingo.
I spent the whole of classtime preparing an eloquent speech and gathering up the balls to make it. Class ended, I fumbled with notebooks, stuffed everything into my backpack, and followed her out. She was halfway down the stairs when I caught her.
After some initial static, I managed to invite her. She asked with disinterest whether it was to be a date. I said it was. She smiled and said OK. We exchanged phone numbers. I practically skipped home I was so pleased with myself.
We didn’t talk again that week until, on my way to pick her up that Friday night, I called from my car. She said she’d be waiting on the steps in front of Jester. As I turned down the street, I saw her waiting, only she wasn’t waiting alone. A curly-haired brunette with a mouth prone to opening stood next to her. As the passenger door to my single-cab truck opened, Katie asked rhetorically, “Is it cool if my roommate comes?” Cursed as I am with the nice guy gene, I couldn’t say no, so they both climbed in. Roommate sat next to me; Katie, the door.
The drive from campus to El Arroyo took about 15 minutes, but with Roommate yapping about where she was from and what she did in high school, I’m not sure I actually got a word in. Surely none were exchanged between Katie and me.
We arrived at the restaurant to find my friends and their dates waiting. The hostess showed us to our table for 12, but since I’d picked up an extra, we had to pile on a thirteenth chair. During the awkward shifting around and jostling for chairs, I managed to reserve three in a row, pulled out the one next mine, and motioned for Katie to sit. In a not-snotty-but-not-really-polite-either way, she pulled out the third chair herself and sat down. Roommate dived into the one next to me and I found myself the only person at the table still standing.
Feeling as though I’d endured enough of Katie’s pubescent antics, I forced Roommate to get up and move over. I sat down next to Katie, my date. For everyone else at the table, it was a feast of awkwardness. For me, what had started as embarrassment and turned into anger was beginning to feel more like a game.
I don’t remember what Katie ordered but I do remember watching with horror through the corner of my eye while she slopped up her enchiladas like Takeru Kobayashi. The fork went up; the fork went down. Up, down. Up down. It must have taken no more than three minutes from the time the waitress set down the plate in front of her that Katie was wiping her face with her napkin. Stunned, the waitress took the barren plate on her next pass. I looked around. No one said anything.
For the next hour, I ate the most leisurely meal of my life. After repeated attempts to draw Katie into the table’s many discussions, I gave up on entertaining the mute. Roommate was doing all the talking, more even than anyone else. When it came time to divvy up the check, and we took turns signaling to the waitress which dates were together on which checks, I announced most belligerently, “Just me.” I’d be damned if I was going to buy Katie and her uninvited roommate dinner.
We returned to campus and made our way to one of the dorm girls’ room, where the place had been stocked with bottles of vodka. It was party time. But just as we came walking up, Katie decided she felt tired and wanted to go home. More than happy to oblige, I walked her and Roommate across campus to Jester, where, standing in the lobby, we said our goodbyes.
My sense of good form told me a half-hug was the appropriate salutation. There’d be no thought of kissing goodnight, not after the way she woofed down those beans and rice. Plus, I wasn’t diggin’ the love triangle. Roommate wrapped me in a slightly-too-tight-to-breath hump hug. Katie, it seems, had something else in mind as well. When I stepped to offer her my right arm and torso, she hopped back two feet and raised her hand for a high five. I turned on my heel and walked out, totally leaving her hangin’.
More stories of woe
- Winner: Con man
- Second runner-up: Swingin’ surgeon
- Third runner-up: Breakup breakdown Honorable mention: Blind date –>













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