Last week, we asked our readers for their stories about taking big risks. When presented with this challenge,  when given the task of recounting moments of conquered fear, 99% of the responses were about asking girls out on a date. Don't get me wrong, I understand ("what if they laugh at me" has broken more psyches than any Eldritch nightmare) but it doesn't change the fact that the most daunting moment of our lives ended in dinner and a movie



If you have a moment so nerdy that you need to tell the Internet about it, we want you to send your submissions to dorklypwnup at gmail


Pwn Up: Risky Business


Back in the day, my friends and I were obsessed with Tony Hawk Pro Skater for the N64.  Despite my amazing skills at high-scoring combos and hidden tape discovery, I am massively uncoordinated when it comes to anything with wheels, especially skateboards.  Fast forward to my freshman year of college.  There's a cute girl in my area that I have a huge crush on, and I can tell that she likes me back.  She just so happens to confide in me one day that she thinks guys on skateboards are hot.  So, instead of doing the logical thing and inviting her to my place for dinner, I ask my best friend, an avid skater, to teach me how to skate.

Two weeks later, a few of us (Cute Girl included) are all skating together when we come by a massive hill on our campus.  Despite having made zero progress on my skating abilities, I look at Cute Girl and immediately flash back to playing Tony Hawk, and think, "What would TH do?  How easy would it be to take this hill and impress the hell out of her?" So I attempted the hill.

Long story short, I ended up with a mass of cuts, bruises, and my collarbone broken into three pieces.  It took two surgeries, three years, and a small metal refinery of surgical plates and screws to fix.  Cute Girl stayed with me in the hospital.  I asked her out under the influence of morphine, and she said yes.

Three months later, we broke up.

Damn you, Tony Hawk.








Pwn Up: Risky Business


During my last semester of college I had a huge crush on this girl I met through a mutual friend. We hung out a few times and I struggled to act cool around her but didn't really get anywhere. Then one night I decided to take a leap of faith and reveal my nerd side. She asked me to tell her something about me no one really knew and I said that I play MMORPG games and that i'm kind of a big geek, but didn't talk about it with anyone. As it turns out, she had been a closet gamer since middle school when she used to play Runescape on a dial-up connection. We launched into conversation about a ton of different games that lasted till we both fell asleep. After that night, we developed a lot of inside jokes and connected so well that I asked her out. There's nothing like a girlfriend who can own you in Age of Empires 2, go questing with a maxed out toon online, or be your co-op in Portal 2, so don't be afraid to mention it!

- Danny
Pwn Up: Risky Business
imgage via
The biggest risk I ever took was cooking a cake for a girl I liked. She was a nerd like me so i thought it was good to make a Legend of Zelda cake. I accidently turned Link into Dark Link. I ended up just buying her Ocarina instead.
Pwn Up: Risky Business
Sorry if my English isn't good, it isn't my first language.
Two years ago, my class was on a graduation trip that I couldn't afford,  so I still had to go to school. The first day was okay, there was a few of us stuck in school together, but there was also a girl I'd never noticed before. Later she started instant-messaging me, just saying "Hi". At that time, people only talked to me to ask for homework, so I just answered "What do you want?" and after a weird start we began to talk about other things, and I had the best conversation of my life.
We debated about religion, media, differences between people, philosophy, and of course hobbies and interests.
The next few days were amazing, never had so much fun. The people I barely knew were amazing people. But after one week the class came back from the trip. Everything should've gone back to normal, but before we had to go on with the rest of our lives, we all split a pot of Nutella together. It was very fun. The next day, summer break had begun. I wanted to actually ask her out, but I could never find the right moment ( I was dumb, I know. ) and kept delaying untill we started to talk less, just once in a while.
Back to school last year, I thought I had lost the chance, and since she went to another school. I just tried to forget that. In the middle of year, we started to talk again, and I finally took the chance and asked her out. She said yes, and I hadn't experienced that much anxiety and anticipation since they first announced "The Avengers" movie.
We went to the cinema to watch World War Z, (okay movie), and I was really nervous, but as the date went on I started to have fun. I didn't make a move, but we talked a lot, laughed a lot, it was fun. After the date, for some reason she didn't seem to want to talk to me. I couldn't believe that I lost the chance with that amazing person. 
Yesterday one of her friends (and friend of mine) said that she liked the date, the only problem was that I didn't go for a kiss, I didn't ask her out again, I didn't take the risk. 
If you've a chance, don't hesitate it can make you regret the lost opportunity for a long time... After I send this message i'll try to ask her out again, if there's a chance that she still likes me, I'm taking it.
Love, it turns out, is the riskiest undertaking of them all (take THAT "snake handling"). For next week's topic, let's go back to the past. We want you to send your embarrassing creations. Still have that old fanfic lying around? Send us an excerpt. Still have the password to your Xanga account? What about the failed webcomic you and your best friend wrote in high school? It's all for a segment we'll call Pwn Up: What Have I Done? 
Send them all to DorklyPwnUp (at)