The Best Time I Gave a Girl a Mixtape

When I was a sophomore in high school, I had a class with a girl who I will call Jen Carter. Jen was one grade above me in school, and six million grades above me in every other meaningful sense. In light of our differences in age, social standing, and progress up the ladder of puberty, I wasn’t ever going to have so much as a passing conversation with Jen, with two notable exceptions:

1. Situations that took place inside of my head. I am not ashamed to admit there were a few of these. Don’t worry: because at the age of 16 I was still five or six years away from hitting puberty, these daydreams were highly innocent. I don’t remember any one specific fantasy date between Jen and me, but if I had to guess, I’d say there was probably a lot of us walking down the beach holding hands while she lamented the fact that she’d had to wade through so many handsome, popular, post-pubescent guys before finding me. And in these daydreams I was probably dressed like Magnum P.I. and she was probably dressed like Magnum’s beautiful but ill-fated wife Michelle.

2. Situations where Jen sat by me in class. Because of the mandatory alphabetical seating chart.

And so it was that Jen and I became … two people who sat next to each other in class. Jen was always nice to me to when I attempted to engage her. I’d occasionally turn around and say something to her along the lines of, “Man. This teacher is so lame.” To which she would reply, “Yeah. So lame.” And that would be that. One time I gave some sort of class presentation and as part of it I played “Bridge Over Troubled Water” by Simon and Garfunkel. When I sat down Jen said to me, “That song was really pretty,” to which I replied, “As are you, fairest maiden.” Just kidding, I said, “Yeah. So pretty.”

Flying high on the fact that Jen liked “Bridge Over Troubled Water,” I decided to make her a Simon and Garfunkel mixtape. Folk rock from the '60s was what all the cool kids listened to in 1993. I’m not sure what my game plan was, exactly. She’d hear “Homeward Bound” and want to go to Homecoming with me? I really don’t know. But my heart breaks a little bit at my sincerity and naiveté as I remember myself handing the tape to her and saying, “Hey, here’s a mixtape.” Jen was actually pretty gracious as she accepted the tape, although it didn’t induce her to ask me to go to Homecoming. Our class ended along with the school year and we went our separate ways, I to a summer full of water ballooning, prank calls, and fishing, she to three months of parties and dates and boys.

But then one day during the summer my mom sent me to Mervyn’s to buy myself some new underwear. I went with some trepidation, as this was the first time I’d ever bought my own underwear. Still, I figured it was probably time for me to take this momentous step, and I was further motivated by the realization that this was my chance to switch from tighty whities, which were what little kids wore, to boxers, which were what the cool guys wore. Once there, though, I found myself daunted as I faced the entire Mervyn’s underwear department by myself, and I decided that now wasn’t the time to be getting fancy. I headed towards the tighty whities, and as I did I heard someone call out my name. Jen. Turns out she had a summer job working at Mervyn’s. In the men’s underwear department.

“Oh, hey, Jen. How are you?” (I reached in my pocket to see if I’d grabbed the keys that had a little Swiss Army knife on them so I could commit suicide on the floor of Mervyn’s.)

“Good. What are you up to?”

“Oh, just grabbing some stuff.” (Some underwear. Some little boy underwear.)

“Ah. Well, do you need help finding anything?” (Yes. I need some help buying underwear for the first time. Would you, Jen, one of the prettiest and most popular girls I know, mind helping me? Maybe I could even try on a few pairs for you while we listen to my Simon and Garfunkel mixtape? Tell me about the elastic band on these Hanes. Do they tend to be durable?)

“Oh, no, I found what I needed.” (It’s over there at Gart Brothers Sporting Goods. It’s a gun, for my face.)

I was desperate to get rid of her, so I glanced at the underwear on the rack, and figuring that underwear with an elastic band was essentially one size fits all, I grabbed a few packages of the nearest tighty whities and began to bolt to the other end of the store. Jen stopped me in my tracks, saying, “Hey, I can ring you up for those.” As I review these events from the remove of time, I am forced to conclude that Jen was either 1. Incredibly sweet, helpful, and a little oblivious, or 2. A sadistic monster. Either way, I was forced to walk with her to the register, my arms full of tighty whities and my heart burning with shame.

We made casual conversation while she rang me up, and then I headed to the roof of Mervyn’s and jumped off. It’s only two stories, though, so I lived. I went home and unwrapped my new underwear; as I unfolded it I noticed that it simply kept unfolding and unfolding. And unfolding. I don’t remember the exact size, but I think it was in the mid-40s. I believe I was at that time around a size 30. Because they were already open, I put a pair on just to see how they felt. They were pleasantly roomy, and, to my surprise, I liked them. Not as much as I would have liked Jen not seeing me buy size 46 tighty whities, but still, I liked them.

Davis B. photoshopped his picture to make it look like he is bald and chubby and wearing a bow tie so ladies wouldn't try to date him, since he is already married.

Photo via Flickr