Nothing is more depressing than the articles of clothing I bought to impress a girl. Yes, I admit, I do it. Here are my sad purchases in no specific order:
My Abusive Boyfriend Jeans
My sister was nice enough to take me to shop for jeans at Diesel for my birthday. I tried on a lot of jeans until I somehow squeezed into a pair of Euro-tight kind of dark jeans. Very chic, very cool, very tight. When the super-hot little brunette girl told me I looked good in them, I suddenly forgot about the sling-like feeling enveloping my crotch.
I got home, and tucked the jeans away thinking I’d never wear them, and they lie coiled in my drawer waiting to strike my unsuspecting crotch. They were like an abusive boyfriend. When I did wear them, I felt a sense of satisfaction. They made me confident because they were just so good looking and hip. Maybe I could tame them, make them fit right, make them see things my way, and give way on this vice that was the button fly clamp annihilating my crotch.
Despite how beautiful they were they had to also make me feel bad about myself — they squeezed and squeezed telling me: “you’re fat, you’re worthless, you’re not good enough to look good with me, you embarrass me”. And like any good abused person, I kept going back to wearing them no matter how bad they made me feel. Well they didn’t make me feel bad. They made me feel good, I mean bad…I mean I DON’T KNOW!
The Pink Skull Belt
My office is located perilously close to tons of stores on Fifth Avenue. So, whenever there’s an event or possible chance for me to impress a certain girl, my co-workers and I make pilgrimages to the stores trying to figure out how to dress to impress. First I brought my friend Austin along from work to the Ralph Lauren store. I had grown attached to a pink belt punctuated all the way around by navy blue skull and cross bones, and three pairs of socks—one of which was polka dotted with skull and cross bones. Austin battled me: “You’re really going to show up there with skulls on your belt AND socks?” Kind of made sense, but I needed a second opinion. I fished my other friend Briana out to the store so she could come enable me to get both the socks and the belt. “OK, Rich…I think the skulls on the belt are enough,” Briana said.
The event I was going to was a beer pong tournament—the girl in question would be staring at the cups, and all I had to do was Elvis my hips into the picture! Perfect. At the beer pong tournament I strutted in with my abusive boyfriend jeans—we were at that point finally in a great relationship—held up by my pink skull belt. Things did not work out too well. The girl simply didn’t notice my belt. She wasn’t even looking at the cups. I knew it was bad when Briana finally said:
“Oh Rich, you wore your new belt today.”
She knew it had to be called out. To make matters worse, the girl looked at the belt, didn’t flinch, and turned to take her shot at our opponent’s cups.
My Halle Shirt
In college I became enamored of a really cute girl named Halle who lived a few dorms away from me. All of the dorms in our area used the same dining hall. Therefore, like any sane person, I staked out her times when she went to the dining hall and made a plan: I’d hunker up to her table in the dining hall, introduce myself, and ask her on a date. For the event, I would unveil a new shirt. I got this terrible yellow and brown striped thing from The Gap. I rounded up my boys—I needed some support and friends to make it look like I wasn’t psycho. I told them the plan and it immediately got too big. By the time we finally went to the dining hall, I had 17 friends cheering me on.
After we ate, it was time. I left the banquet table, grabbed a cup of coffee on my way and sidled up to Halle's table.
“How are you guys,” as I sat down across from her. I literally swooped in. Halle’s friend sat there with an expression that said half: “what the hell is he doing,” and half “who does this sly son-of-a-bitch think he is?” I don’t remember what was said, but I remember it being very smooth.
However, just as I was about to ask Halle to get together, disaster struck. My hand inexplicably had some sort of spasm (perhaps from all the un-smoothness that was building up due to my consecutive minutes of smoothness), and slammed down onto the spoon protruding from my coffee cup. The cup flipped into the air, turned completely upside down and (before I could wish that Isaac Newton never sat under that apple tree) it made its decent…physics, on this day, would not cut me a break. Everything seemed to slow down. I heard individual conversations from each cluster in the dining hall, I had epiphanies, somewhere in the Brazilian jungle a venomous snake snagged a plump frog as a meal. And, from my banquet table of supporters a slow motion echoing: “noooooooooooooooooooooooo!” But it was too late: the coffee cup landed, all over my new Halle Shirt. I was drenched…and burning.
I stood up: “I have to go…”
And, with that, it was over. On that same evening, the Halle Shirt was thrown in the trash…along with all the lessons I thought I was learning.
An interesting post script to this story—Halle and I eventually became good friends and made out right around graduation just to say we did it. After we made out, we looked at one another, laughed, and said: “well that kinda sucked, didn’t it?”
A smart, funny, attractive guy who not only admits to being clueless about women but is willing to share his dating diary? Tap your inner Bridget Jones by offering him your advice.
