I nailed the hottest girl in school….

I nailed the hottest girl in school….

I nailed the hottest girl in school…. After she got fat.

You can never say emphatically that there was or is a hottest girl at a school of over 2,000 students. There is, however, certainly a cutoff for where girls go from hot because they’re attainable, to hot because they could be a celebrity, to hot because just thinking about not being with them makes you cry while masturbating to them (that process is called Cry-sterbating.)

Steph was firmly in the crysterbating camp.

She was tall, legs athletic from swimming with an ass like the dot of an upside exclamation point at the end of them. Breasts bigger than a handful, but not big enough to pull her down; good posture makes them seem bigger. Her hair was cut short and blonde, the androgyny somehow accentuating the femininity. Facial features sharp and sarcastic, with eyes that didn’t believe your bullshit for a second. Steph was the punker chick that the jocks, preps, and everyone else couldn’t have. And, she was awesome.

Due to a classic case of being held back a grade for stupidity, I reaped the benefits of my failed public education, as I was the first person in my grade to get a car. Overnight, I went from the awkward nerd without a definite clique or social strata, to the go to man for everyone. I was straightedge before that was thing, but I never let that stop me from hanging with the punkers and wiggers who wanted a ride someplace to do that stuff. I had badass friends doing cool things… plus, sometimes I had Steph in the car.

Occasionally she’d be dating this or that friend, and when this or that friend needed a ride, she’d be right in my back seat. I’d find a way bring her into whatever the hell nerd conversation I was having, doing whatever gymnastics it took.

“Did you ever see Monty Python and the Holy Grail?”

“Nah, I don’t watch movies.”

“Oh that’s cool, that’s cool. Its like… do you watch Beavis and Butthead?”

“Nah, I’m not huge on MTV. Sometimes its fun to get stoned and watch the Xgames though. Its fun to watch the skateboard kids wipeout.”

“Totally, that’s just like Monty Python and the Holy Grail!”

School life goes on sadly (or thankfully in most cases), and sooner or later everyone else had their own cars and the reasons to keep hanging with me were prohibitively low. I saw Steph less and less, each viewing somehow making her grow more and more attractive. By graduation she was just another lost cause, a pretty girl I was afraid to ask out. By the middle of college, she was a name that had resonant boner associated with it but not much else. By the time I graduated and was living with my college girlfriend, Steph was finally relegated to a ‘Hey, what ever happened to Steph?’

Then, a funny thing happened. I broke up with my college girlfriend, found myself back in my hometown, and discovered social networking. Suddenly, any stray curiosity I had about any person I’d ever considered was right at my fingertips.

Growing up as the nerd that I was, I had a few lingering regrets about the ones that got away because they never knew that they were being pursued. Steph was one. THE one.

Nuance was never my strong suit, so I decided to not beat around the bush. I friended her and then I sent her a personal message. It went exactly like this:

Hey Steph,


This is going to be a bit out of left field but bear with me.


So, I’m leaving the Philadelphia area at the end of the summer to try the indie filmmaker/aspiring comedian life in NYC, basically giving myself a new life to start in pursuit of the dream.


But, before I leave the area (not that NYC is exactly the other side of the world, but you know what I mean) I have decided to throw caution away and am now trying to rectify any regrets I may have.





One of those regrets is that I never asked you out.


So, I’m doing that now:



Hey Steph! Would you like together this weekend for maybe a drink or something in Philly?



The way I view it its win/win. Either we have a good time, or you get a free meal, some drinks, and some decent gossip for the rest of the week.



Okay, that’s what I got for ya. Looking forward to hearing from you.



I watched when the message went from being listed as ‘sent’ to ‘read.’ And I waited the wait of the condemned. I might have had more confidence than I did in high school, but that pessimistic attitude of the perennial single dies much harder.

Still, despite my poor outlook, it happened. She said YES!

It was the joy of joys. Steph and I were going out! The hottest girl in the school and me!

I did notice one thing though…

The correspondence and subsequent date took a rather long time to set up. There were pauses and last minute engagements and bad weather to beat the band. I was planning on moving to another city by the end of the summer and it was already July without us having met up. I thought she was ducking me; hot girl buyers remorse, I supposed. That was until we set a date and she mentioned a caveat. This, I’ll paraphrase.

“I feel compelled to tell you that I don’t look the same way I did in school.”

I told her I appreciated her honesty, and that I still wanted to go out with her. I know that time changes people, and but a few pounds wasn’t going to change my resolve. The date was on and we went.

Then I saw her.


To quote on oldie but goodie from my father, Steph had sat on an air hose.  The sharp features had been filed down to VW roundness. The breasts that had protruded proud from her tall frame now hung as albatrosses under their own girth. She still had the ass, but plenty more of it and thighs to boot. The androgynous hair was still there too, but the childbearing hips that had borne no children betrayed its effects.

This was what the warning was about.

In full disclosure, I had been told by various friends that Steph had gone through a rough patch and didn’t quite come out the same. The term ‘hot mess’ had been bandied about with relative abandon.

My friends had not steered me wrong. Steph had had it rough.

The drug culture of the punkers drove her to work at a pharmacy specifically to bring home discount party favors. Addiction bred addiction to various pills and powders ill gotten from work, or ill gotten from the ill gotten. At some point, she dropped her boyfriend of a few years with whom she seemingly had settled down, and went on a tear with who could get her what. STD rumors abounded but none were verified (or true). And just when things seemed they couldn’t get bleaker: her father died. He was always the one she was closest to, so of course, he was the one who took his own life when he found out that her mother was cheating on him.

All the habits she had before shot a dose of steroids, doped their blood and took off for the Tour de France. She was accessible to anyone who was interested for the right price. Never an official handshake agreement, but it was understood by anyone who knew her how to go about it. Steph, despite her snowballing failings, was never stupid. In a misguided defense, she took to fast food for protection. All the boys who had lusted after her were now being faced with the dilemma of her own concoction: who wants to fuck her now that she’s not the hot chick anymore? Unfortunately, with loss of looks goes loss of self esteem, whatever might have been remaining. Her bar for validating her looks lowered to who ever might be willing. Plus, the guys who were willing before stayed surprisingly willing still. Apparently those who bribe chicks into sleeping with them with drugs aren’t the pickiest lot.

By the time Steph sat herself down at my table for a drink, she was on the other side of a year of therapy, a stint in rehab, and reconciliation with her mother. She still had issues aplenty, but at least she had far fewer habits.

After her life story, she wondered if I asked her out, out of pity. She knew I had a reputation for being nice. Frankly, at times I also wondered the same.

That’s not how the date felt though. That’s still not how it feels.

What it felt like was the hottest girl in the school was going out with me. ME!

I felt like I was lucky to be there, and I brought that feeling to the table where we shared drinks and talked about our lives since days gone by. I brought my school boy crush along with me.  When I fell for her the first time, I didn’t know much of Steph, beyond the gorgeous and the sarcastic. That part was ingrained in me, and that’s all I saw when I looked at her. Under the extra marble was the statue, still the masterpiece it ever was for those wanting to look. Now with her story, I was seeing the art take on new meaning. A meaning with troubles and demons, but a meaning with strength and will to battle.

She was the unattainable. She was the awkward conversations in the car. She was the tearful sessions  spent alone hoping for what might never be. And here she was.

And she could see it in my face.

She saw herself through my eager but nervous smile. She saw herself through all the jokes I was catering just to make her laugh. She saw herself when I was too nervous to kiss her at the end of the first date.

I hadn’t followed Steph’s reputation. I only knew the girl I knew. That was the girl I longed for and missed. Steph missed that girl, too.

For a few dates, she was that girl again.

Steph knew I was moving away, and we talked about how we were going in different life directions. We were adults and knew where things were headed.

On the third date, things came together physically. We only did it once. It was affectionate and slow. I looked her in the eyes the whole time. She was embarrassed by the looking, but enthusiastic. When it was over, I smiled from ear to ear. So did she.

I moved away shortly thereafter, and she moved on. We’ve stayed in touch and hang out when back home for the holidays. Sometimes we talk about our current loves and sometimes we giggle about our one time affair. In a peculiar quirk of fate, its made our genuine friendship that much stronger.

I’m not a blind man or saint. I sometimes wonder how much better it would have been if this had happened back in high school: She at the peak of her hot, and me at the valley of my awkward. Though, I think ‘better’ is the wrong word. It would have been a victory for me, for sure. It would have been future masturbation fodder without a doubt. It might have been just the confidence booster I needed to carry on to a more successful future, but that’s pure speculation.

The fact is, for us to happen in the glory days, I would have needed to be a different person or she would have too. Instead, it happened when we were different people. We were grown ups. But, for a brief moment, I finally got to be the nerd that got the girl, and she got to be the sought after hot chick everyone wanted again.

Fair enough.

About Jake Serlen

Jake Serlen once published an essay about oral sex in National Lampoon's. He received $50 for his efforts and was happy to get it. He lives in New York City.


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