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Chris' High School Experience & Why He Was Semi-Popular Senior Year (Includes Old Photos!)

Good Looking Loser
June 29, 2014

My High School Experience

I've talked a little bit about my teenage years in "About Good Looking Loser", but lets expand on this a little bit more.

I gave you advice if you are in high school and the experience hasn't been great -

I'll have to do some more posts but the above and subsequent discussion covers most of the surface.

The pictures below are mainly from 2001-2002. I'm 18 or 19 years young.


Chris' High School Experience

I went to Winston Churchill High School in Potomac, a small town in Montgomery Country Maryland.

Potomac is a extraordinarily wealthy town. An elitist place.

Something like ~40% of it's residents have graduate degrees and the median household income (after taxes) eclipses $100,000.

Some of Potomac's neighborhoods are among the most wealthy in North America.

Many years, per certain criteria, Potomac is routinely considered the wealthiest town in America. 

Some celebrities live there, (notable - Mike Tyson, Daniel Snyder (Redskins' billionaire owner), Patrick Ewing (NBA Hall-of-fame center) Richard Marriott (neighbor, Marriott Hotels & Properties), John Glenn (neighbor, 2nd man on the moon), politicians from all 50 states have a residence and the gas prices were over $4 long before the rest of the nation saw this absurd increase.

The public school system is also considered one of the very best in America.

Not a lot of wealthy families find it necessary to send their children to $55,000/year private preparatory high schools.

Some do however.

Darren Star, the executive producer of Beverly Hills 90210, Melrose Place, and Sex and the City is from Potomac, MD. He actually went to my high school (in the 70's).

The premise for the wildly popular 90's show "Beverly Hills 90210" was based on Winston Churchill High School and the town of Potomac (and Bethesda, MD.). 

A town where - 

Highly superficial kids in super-exclusive cliques that drive BMW's and have an allowance that is more than most of their public school teachers.

Social climbing is the meaning of life.

A survey was taken in the year 2000 (sorry, can't find it) about which high school would be most likely to have a mass-murder shooting incident similar to what happened at Columbine High School when unhappy unpopular teenagers lashed out at their more popular classmates and teachers. 

Winston Churchill High School in Potomac, MD. won. 

There was a significant amount of bullying at my high school and popular kids flexed their social status muscles to make other's lives miserable for pure amusement.

Girls were especially cruel to each other.

The endowed popular cheerleaders would make it a daily activity to remind the lesser blessed, lesser popular girls that were inferior and that no guys paid attention to them. They would laugh about it at sleepovers and relentlessly prank call the unpopular girls to remind them that they were genetic trash and in for a life of pain and rejection.  

I remember that one girl had her house and lawn covered in toilet paper and [supposedly] written in chalk on the driveway was the word - 


Even though I wasn't really popular, at times, even I took enjoyment in bullying those less popular than I.

As late as 11th grade, me (and some friends) made one kid so miserable that he transferred to another high school when he finally couldn't take any more of our terrorism. 

I deeply regret this and every other kid that I/we hurt.

The social system was brutal.

Kids took joy in hurting each other. 

Everyone I know got caught up in some form the bullying.

Some with physical violence, others with AOL Instant Messenger and other forms of 90's cutting-edge cyber-bullying.

I got bullied, I got picked on, I got fucked with (until 11th grade) and I gave it right back to some kids that weren't as popular as me.

It makes me sick how badly we treated some people and the lasting effect we probably had on their lives.

A small part of my motivation behind creating Good Looking Loser is to give back and help those guys grew up hard and without cool friends or female attention.

I quietly root for the kids I went to high school with that weren't popular.

I'm friends with a lot of my high school classmates (both popular and less-popular kids) on Facebook and the reality is - very few of them Get Laid or have hot girlfriends - most of the unpopular kids mostly all ended up as undersexed loners. 

It actually makes me mad because I know where their poor self-esteem began - the same place mine did. High school.

It's a shame and I honestly don't know why (God?) picked me to have a great life.

cellphone daytona2blog

The 20854 In-Crowd

I don't know if the situation I describe is different than any other high school in the United States but I will say this -

There was a distinct IN-CROWD.

For the most part, I was not a part of that crowd.

I was an outsider.

At best, I had a few popular friends that were willing to include me - even if it wasn't a super popular decision to be seen with me. Even though many of them later ditched me under social pressure from their more popular or older friends, I am grateful for the times we shared. I'm not bitter about it.

What has always left a bad taste in my mouth is how most of the formerly popular kids wouldn't ever want to be seen even talking to me.

Although I'm as "In-Crowd" (Hollywood) as someone can get these days (particularly my late 20's) -

I know what it's like to be an outsider.

I know what it's like to stand on the side at school dances with my head down hoping no one saw me.

I know what it's like to not get invited to parties by kids that I thought liked me.

I know what it's like to have nothing to do on the weekends.

I know what it's like to be teased when my brother died from cancer. (4th grade)

I know what it's like when popular kids would talk to me with the only intention of getting something from me or having me entertain them (I was a funny kid). 

I know what it's like to be scared to death of the popular girls and masturbate to them later in the day.

I know what it's like to be a unsuccessful follower.

All of these traumatic experiences built a mountain of social anxiety that would take years to overcome.


But in so many ways, however, my high school experience made me who I am today.

I was so deeply insecure that I turned to "self-improvement" as a way to get noticed/hide.

Somehow, it really worked out for me.

To set the context, it's important for you to know that I wasn't a total loser without friends.

I was never a total loser. 

I had friends and many of them were somewhat popular.

A lot of us were on the hockey team and we were pretty good too. We just weren't super popular and we didn't have access to the hot girls or access to the cool parties. I had slightly above-average popularity with guys and slightly below-average popularity with girls.

A lot of that completely changed toward the end of high school.

I got noticed and I became somewhat popular.

Most importantly - the hot girls now liked me.

weeksantaI was taking selfies long before you motherfuckers were.

So What Changed...?

There were a lot of little factors that played into my rise to popularity during my Senior year but much of it dates back to 11th grade when I all but quit my first love - ice hockey.

The sport that I thought I'd be playing professionally for a decade lasted only about 3 years. 

Let me tell you about ice hockey, it ended poorly but I'm still proud of some parts of it.

chrissugarrayChris' Short Ice Hockey Career
(this about ice hockey, my roller hockey career was a fairly big success)

In 8th grade, I wore hockey jerseys everyday to school.

I told people I was good at hockey, I was - Street/Roller Hockey.

When people asked me what ice hockey team I played for, I didn't have an answer for them.

I would lie and make up some vague answer.

The truth of the matter was - I didn't even know how to ice skate.

Toward the end of 8th grade, I started taking private ice skating lessons from an intense woman named Nancy Lucci.

As an 8th grader, I would skate around on figure skates in my tight tapered jeans on the little girl's rink while the high school hockey team was practicing on the big rink.

Playing real ice hockey seemed quite far away. I just wanted to stop falling down.

Since I was pretty skilled on rollerblades, I was able to pick up ice skating pretty quickly. 

Nancy was impressed and told me I had legitimate potential if I stuck with it.

In fact, hockey is the only thing I ever did well naturally.

All this other stuff - getting big/strong in the gym, sleeping with hot girls, having a big dick, getting into Law School, etc., etc. required a tremendous amount of hard work to even be slightly above-average.

But Hockey was easy for me.

Before I knew it, I was a high school Freshman and found myself at a 5 am tryout for Winston Churchill High School's Ice Hockey Team.

Even though I had only ~1 year of ice skating behind me, I made the varsity team which had some of the best players in the state.

I was big for a 9th grader (6-2, 160lbs), I could skate really fast, I had a good shot and most importantly - despite my inexperience, I could play with guys that had over 10 years of experience. 

Long story short, 9th grade was an incredible year for me athletically.

I had the respect of the veteran players and it seemed like I was headed for big things.

That summer, I was scouted by the Rochester Junior Americans to play in one of the more competitive leagues in North America.
(to be honest - on a skill level I had no business being pursued by the Junior Amerks, they just though I had potential since I had developed so quickly)

But I didn't move to Rochester.

Unfortunately, ~10-11th grade is when the dream started to go down the toilet.

My attitude changed.

I wasn't one of the best players on the Varsity Team (not even close) but I felt I should be getting more time and that the coaches were partial to the Jewish players.

I felt I had the highest potential of any player on the team (I did) and was wasting away on the bench with a coach that wasn't interested in developing me.

I started to regret not moving to Rochester.

My teammates were aware of my piss-poor attitude and some them were jealous that I received attention from the Junior A program. They made life hard on me.

My attitude got increasing really sour and I stopped enjoying the game. I was feuding with my coach, teammates, friends and parents. I was crying myself to sleep. Due to a wrist injury and the nightmare of a coaching situation, I made the decision to step away from the game for a while. It proved to be a great decision - I never came back.
(I still continued to play roller hockey competitively, I was better at that and had a lot of fun)


My Next Total Obsession - The Gym

The gym was my next obsession.

My Dad bought me a Smith Machine and some dumbbells for our basement and I used to work out for 2 hours a day, 5 or 6 days a week, with my shirt off and music blaring.


It was so therapeutic, it was incredible.

I didn't miss ice hockey. 

I started to look REALLY good and people were starting to take notice.

Girls would want to touch my arms and take pictures with me. 

Guys respected me and would feed my ego.

I loved the newfound validation and would spend the next 10 years (until I was 26-27) completely obsessed with my appearance. This would prove to be a future problem.

In high school though, it was my ticket to above-average popularity and attention. 

My face started changing, my body started changing, I had abs, I had a nice butt and I even won "Best Body" during my Senior Year.

It was a silly award but something I worked incredibly hard for and absolutely secretly cherished because the majority of voters were girls.

To give you perspective - I was 6-2 170lbs at my best, full 8/10-pack of abs, my arms were probably 14.5 inches and I couldn't bench 225 or squat 225 even one time.

Hardly impressive numbers, but for a high school kid it was pretty good and I had the whole "model" look going. Tall, super low body fat and some muscle.


The Girls - The Ultimate Validation

The most incredible part of my gym obsession was the amount of girls that started to notice me.

Girls that hadn't even spoke to me were telling their friends that I was "hot".

I was mentioned among the best looking guys (who were a lot more popular than I) in our school and even given a scholarship by our church for my "bodybuilding" pursuits. 

Even the girl (Erin) who won "Best Looking" told all of her friends to vote for me. One group of guys that really disliked me nominated this obese kid in hopes that I wouldn't get the award. I beat him by a landslide.  

Girls would routinely try to take pictures with me and introduce themselves.

Random girls would yell out, "Chris/Number 59 is hot!" at my roller hockey games.

Girl from other schools considered me "that guy" and wanted me to notice them. 

The height of the experience was following Senior year when I briefly dated a girl who won Ms. Teen Maryland.

She was one of the main reasons I developed a ridiculous "Sense of Entitlement".

For a kid that didn't even have many girls as friends, this was just about the best thing that ever happened to me, even thought it lasted a very short time and I got my heart broken.
(fun fact - she and I are still friends today)

A lot of girls made themselves available to me but I really didn't know what to do about it. 


I also had an unhealthy attitude about it.

I loved that girls at my high school noticed me and talked about me.

It gave meaning to my life.

It made me insecure instead of COMPLETELY insecure. 

But a big part of me was more bitter than ever. Girls were only interested because I became good looking when years before - they wouldn't even speak to me.

I turned down a lot of girls with pride.

Some girls - right to their face.

I decided I was absolutely not going to hook up with any girls wouldn't give me the time of day just 1 year ago.

I told myself and my bewildered friends that "I WILL NEVER SELL OUT."

While this was a temporary absurd self-esteem boost, it cost me dearly.

I went to college with very little sexual experience and a huge ego.

It was probably the main reason I only had a average sex life in college.

I was scared and still terrified of rejection.

I remember was it felt like to be invisible.

To this very day - I remember it quite well.


My Advice to Unpopular High School Kids

If you are in high school and reading Good Looking Loser, chances are - you aren't part of the exclusive In-Crowd. 

I wasn't.

Chances are - you can relate to how I felt before my Senior year. Invisible. 

First off -

High school is simply an era.

There's no reason in the world that you can't have a killer social and sex life in college and for the rest of your life.

You might have to do a significant amount of emotional repair and develop your sex appeal and Swag Factor.

As I discuss in "What You High School Kids Need to Know" -

My advice is to become OBSESSED with your appearance.

It is your ticket to self-esteem, validation, friends and pussy at that age.

If you have never had a nice body (lean face, low body-fat), you have no idea how girls respond to it. Especially younger girls that prefer HOT over cool.

You might not even know how good looking you can be.

You will have to chance to rewrite your social/sex life in college.

Make sure you look incredible before your Freshman year of college.

Keep it natural and learn about nutrition.

Eat lean protein and avoid those sugar-filled drinks that your friends are drowning themselves in.

Let them tease you about your diet and how much less body fat you have.

Make sure you have awesome abdominal muscles, decent legs and good arms.

Low body fat and ripped abs are the most important

At some point you'll need to develop your "game", other areas of your life and become legitimately secure with yourself.

But your #1 Goal should be to look absolutely incredible and get reminded of it on a daily basis.

There's a lot worse situations than being a timid high school kid with a killer face and body. 

That's right -

The gym (sex appeal) should be your #1 Goal if you aren't popular in high school.
(or even if you are popular)

Get your ass into the gym and become sexy.

Use all the insecurity in a healthy way and get an incredible body (abs matter most) and a lean face.

The validation will come, respect/hate from guys will come, attention from girls will come and later real confidence will come.

Don't turn down many girls that are interested.

Be thankful that you are coming up in the world.

Don't be an arrogant fuck like I was.

Don't end up an inexperienced arrogant fuck like I was.

A "Good Looking Loser".

Go to the parties you get invited to, even if you just talk to the kids you know.



Forget about cold approaching girls and trying to be like your favorite "pick up artist".

You would probably trade places with him if you knew how sexually active he actually is (or isn't). 

Cold approach, though super productive for some, is usually a "last resort" for most guys in search of something that even resembles a sex life.

I can't overstate how big of a deal this high school upperclassman period was for my entire life.

I left high school as a "big deal" and it undid the vast majority of traumatic experiences I suffered in the previous 11 years.

I'm not a fan of living in the future but if you aren't popular, just know - better days are ahead if you can make yourself look good.

parismt runVintage Good Looking Loser (2003)

My Attitude Toward My High School Experience 

I truly love my life today.

I do.

I can get hot girls (I also have a beautiful long-term/sometimes long-distance girlfriend), I'm wealthy, I have all the free time in the world and I have a "career" (Good Looking Loser) that I love.

I don't even like talking about it because I don't feel like I don't deserve half of it.

Talking publicly about success is something I have never done well with. 

I've been given so many 2nd and 3rd chances - it's fucking ridiculous and embarrassing. 

I'm proud of all of my decisions to relentlessly pursue my goals.

I'm proud of my decisions to quit certain things and never look back.

Still, I remember high school like it was yesterday.

Every once in a while, I'll have a dream where I'm back in high school.

In the dream (often a reoccurring dream) -

I remember the exact feelings and emotions I felt when I was a relative outsider. Hoping not to be seen. Earning temporary status points with popular kids for a funny joke or some impression that I did.

I remember how sick I was of everyone, including myself, most of the time.

Hoping my future would be better but feeling absolutely powerless most of the time.

As much as I wish I had been popular in my early teenage years, I'm happy that I got to be somewhat popular during my Senior year so the entire experience didn't leave an awful taste in my mouth.

Still, as absurd as it sounds, there's still a part of me that probably wants praise and respect from the kids in high school that considered me a loser 15 years ago.

I don't think that will ever change, even if I've been with more women, have more money, or are become more popular than all of them combined. 

Michael Jordan feels the same way about the high school coach that cut him.

Aaron Rodgers shares similar sentiments about a college professor that told him that he'd never play professional football.

Even Kobe Bryant refers back to certain kids from his childhood that doubted him or teased him.

I don't consider that kind of attitude an unhealthy "grudge" if it doesn't keep you up at night.

It can be motivation.

Once every 6 or 7 months, I'll see an update or picture on my Facebook news feed about some washed up popular kid getting married to a beached whale or wearing outdated clothing while partying with hideous girls that aren't interested in.

I can't help but laugh to myself. 

Yet at the same time, I realize it's totally pathetic that I even somewhat still feel this way about my high school experience.

But at least I admit it?

Overall though, I acknowledge that the deep insecurities I developed in high school were my primary fuel to really start working on myself and become an independent, successful man.

In that respect, I would absolutely do it all over again if I had to.

If one song I've heard in the past few months sums up 90's music (the best decade of music), it's this one -

TheRedArchive is an archive of Red Pill content, including various subreddits and blogs. This post has been archived from the blog Good Looking Loser.

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Title Chris' High School Experience & Why He Was Semi-Popular Senior Year (Includes Old Photos!)
Author Good Looking Loser
Date June 29, 2014 12:00 AM UTC (8 years ago)
Blog Good Looking Loser
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