Welcome back to another addition of times I’ve failed at life. Yesterday we discussed spotting, my incessant sweat stains, and the best way to use human hair as currency. Without further adieu, here is Part 2 of my most memorable fuckups. Enjoy!
Suck it Trebeck
So, two of my biggest character flaws are: 1) always having to be right and 2) talking way too much. Both of those came to light in 2008 during an episode of Jeopardy. The girl I was dating at the time and I had a nightly routine of watching jeopardy and keeping score. Ya know, because it was college and I was apparently a middle aged retiree with shitty hobbies.
Anyway, I’m super competitive, and I didn’t like losing to her. One night we’re watching an episode, got distracted, and started to hook up. I guess the combination of Daily Doubles and useless knowledge was a fetish.
Fast forward, one thing led to another, and next thing I know I was getting a blowjob. On my penis. From a girl! Boom!
Guys, I don’t know anything about the Karma Sutra, but I can’t imagine anything better than 3rd base during a Potent Potables round.
Shockingly though I ruined the moment because mid-fallatio I actually answered a fucking question.
Gentleman, want to know my 2nd favorite way to ruin a romantic moment (if she’s not spotting of course)? Yell, out an answer to a fucking TV game show while a girl is begrudgingly going down on you. Nothing says, “I appreciate oral and effort like an outburst of “What is Great Britain!”
Get Outta Here Ball!
I mentioned yesterday that I played college baseball. Remember? It was when you were reading my article and were like, “Oh shit. I’m totally impressed. This guy seems cool AF.”
We’ll keep this short, but in 2007 we were playing some bullshit game in middle Georgia against a Junior College. Naturally, I was batting 3rd because I was the best hitter on the team/ conference/ Earth. And you knew that every time I came to the plate because my walkout song was “Bossy” from Kelis (not a joke).
Full disclosure, it was a “JV game” our head coach set up so he could recruit. Whatever, let me have my fucking moment. Anyway, my first at bat the pitcher threw a 91 mph fastball down the middle, and I fucking hit it a mile. Listen, I’m not just saying this, I have never been as confident about anything in my life as much as I was about this ball landing roughly a mile past the right field fence. How confident was I? Let me tell you.
Confident enough to yell, “Get outta here ball!” and awkwardly fumble a bat flip down the first base line…
Then the ball hit the top of the fence, and I had to hustle out a double.
Everyone had a pretty good laugh at yet another underachievement of mine. The only person who didn’t was the next hitter who was hit in the ribs with a fastball on the next pitch out of retaliation because his “teammate” decided to pimp a double like he was Babe fucking Ruth calling his shot.
Also, here’s the worst picture I’ve ever taken in a baseball uniform or life…
Balls Deep in Ignorance
Remember, that whole late bloomer theme from yesterday? Yeah, we’re gonna ride the fuck out of that train. Not only was I a late bloomer in regards to sex, but I was also a late bloomer in regards to knowing literally ANYTHING about sex. Case in point – When I found out what “balls deep” meant…at the age of 27.
So, sometime in 2012 I’m at a bar with a group of friends. Guys, girls, alcohol, etc. It’s basically a perfect storm for me to embarrass myself.
At some point during the conversation, there was a reference to someone or something being “balls deep.” And, everyone laughed. Then, I panic laughed to fit in despite not understand a fucking thing they were talking about. However, I didn’t stop there. I awkwardly mumbled aloud, “Ow. Sounds like a stomach ache.”
And, of fucking course I said it as soon as the everyone had stopped laughing and the entire table fell into silence. After a series of awkward looks someone finally said, “Wait. What did you say about a stomach ache?”
Naturally I played it off, and no one was the wiser about my ignorance.
I’m fucking with you. Jeff, and my buddy Justin Wilson, called me out immediately and said, “Wait, what do you think that means?” And, then I said OUT LOUD TO AN AUDIENCE OF NORMAL PEOPLE that I thought it meant a guy was having sex and he ACTUALLY put his testicles into the vagina along with his penis. To my defense, that would definitely cause a stomach ache.
Sadly, I was wrong. Because 1) I’m an idiot and 2) that’s not even physically fucking possible.
“Every Kiss Begins With Cray”
I’m not even gonna get into this story, but just know that in 2010 I was in Nashville for a Garth Brooks concert with my then girlfriend. I don’t know what happened afterwards, but we apparently got into a huge fight.
And, instead of admitting wrong (because I’m sure I was) I decided to be dramatic AF and up the ante by FAKE PROPOSING IN THE PARKING LOT OF THE TENNESSEE TITANS STADIUM.
I don’t have friends in low places. I’m just literally the low places Garth/ Chris Gaines was talking about.
That being said, Gentleman, there is literally no reason to buy an engagement ring for a girl because you can literally get down on one knee with an imaginary one and still woo bae. You’re welcome.
Antacids and Bigotry
So one time in 2011, I was playing trivia at The Bucket Shop in Atlanta. They had a unique twist to their trivia where their Halftime round was just a series of 5-6 riddles you had to piece together. However, the host was super cool, and he would walk around to each team and give hints with one, and only one, riddle the team was confused about.
The entire round was themed about “Snacks” and the riddle was – “Richard Simmons prepares a joint.”
So, the host comes over, we tell him we’re confused, and he says verbatim, “Ok, so a lot of people think Richard Simmons is…” I yell out, “Gay!” Luckily several people felt the same and it was a chorus of bigotry instead of just me.
Then, he asked, “So when you’re ‘preparing a joint’ what do you do?” He then ACTED IT OUT and did a hand motion of rolling a joint.
Me being the team captain of this C’s get Degrees trivia team yelled out, “You Roll it! Roll! Aids! Rolaids!”
Nope. (To my defense…that is next level type shit thinking. Like Nasa level shit.)
Sadly I was greeted with a sea of silence and judgmental looks, as the host scoffed and said, “Fruit Roll Ups.” And slowly walked away in disgust.
So, in case you were wondering – a fun way to literally NEVER make friends in a crowd of strangers and sexual tolerance is to make a terrible incorrect assumption involving the worst disease in the world because you don’t understand snacks or how to filter yourself. Yikes.
Sophomore year of college we were on a baseball road trip to Valdosta. Now, let me first say that there is literally no way to preface this story where it will make it any less weird. At all.
Basically, we had a game rained out which left us with a lot of extra time in the hotel, and after hours of boredom and team building/ failed trust falls I decided to ask a very important question I was confused about.
“What/ Where is the clitoris, and how do you go down on a girl?”
Now, there are a lot of ways to go about answering this age old question. And literally ALL of those ways would sound healthier and less uncomfortable than how I found out…
We could’ve used google. They could’ve just given a vivid description that would’ve been burned into my memory for future reference. Any of those things could have happened. But, they didn’t.
Instead, Jeff and our catcher Nick Waldrip drew me a diagram and put on a tutorial…on Jeff’s nipple….using the nipple as a reference point and pseudo stand-in for a clitoris.
BECAUSE THAT’S WHAT FRIENDS DO.
No, I have no idea or explanation as to why this was accepted. Regardless, I learned a lot that day. And, while I still don’t necessarily believe female orgasms or the clitoris is a real thing, I’m thankful for that sex ed class about spelling the alphabet with your tongue at a Knight’s Inn in Valdosta.
You Booze (And Cruise) You Lose
In 2012, I somehow got hooked up with 2 free passes to a Bud Light booze cruise at Lake Lanier.
The party ended up not being a cruise bit instead was a trio of house boats tied together with a bunch of what I like to call “$30,000 millionaires” with great bodies and bad personalities “ballin out.” For whatever reason I didn’t really fit in.
That became very apparent when a petit Asian girl tried to jump from one boat to another and accidentally fell 3 stories in between the two docked mini yachts. There was not a lot of room for error during that fall. It could’ve easily been a very very tragic story.
And, that’s why it was not okay for me to yell out, “It’s fine! It’s fine! Sometimes you have to let go and let God am I right?!” Then I proceeded to literally tip my entire wallet to the blonde behind the bar. Because nothing says, “Hey I’m impressive please date me!” like yelling out inspirational Facebook quotes during a near death experience and then tipping $11 and an expired Student ID card.
I dated a girl in college that was only able to be “satisfied” (I mean have an orgasm y’all LOLOLOL) by dry humping. Yep. You read that right. Worse, it was only pleasurable for her with clothes on. Specifically, her wearing jeans, and me in khaki shorts.
Now, I want to honestly preface this by saying I was ok with it because I was legit in love with this girl, and chivalry’s not dead. No, it’s alive and well in friction induced sparks from a pair of Mudd Jeans and Dockers.
That being said, no matter what my love and commitment level was for this girl it doesn’t make this situation any less funny today. Especially when you think about how that conversation had to go down.
You’re making out, some heavy petting immediately follows, and then you let the mood take over and start going at it when she says those magical words…”Let me slip into something a little LESS comfortable.” Jesus.
Anyway, one afternoon in 2008, we are going Ham on some preteen dry hump session shit. Then, her roommate came home, so we had to move to the floor. Now, this is shitty apartment/ student housing in college. So, the carpet on the floor was thinner than a bulimic and less forgiving than a Southern Baptist father with a gay son.
My (almost) pleasure turned into immense pain, and I spent the next 8-10 minutes gutting out a miserable ass chafing that no amount of Gold Bond would heal.
Finally it ended. I immediately ran into the bathroom because the pain was so bad I was worried I was bleeding. Now, that seems crazy. Why? Because 1) It is. And, 2) no self respecting man should ever dry hump so vigorously to the point of drawing blood.
I looked in the mirror, and have never felt so disappointed in myself. I didn’t know what to do. So, naturally I ran from building 2 to building 10 at The Grove in Milledgeville to consult and confide with my mentor, you guessed it, Jeff.
Sadly, all he saw was a man literally scarred from confusion and commitment. He opened the door and said, “Are you ok?” I never said a word and walked 2 steps directly past him and I pulled down my shorts/ sex pants.
That’s when I revealed 2 mirrored/ parallel bloody skid marks on my ass cheeks from an afternoon of not delight.
He immediately started laughing and said, “You’re a fucking loser Chris.” Haha. And, he wasn’t wrong.
Mmmbops and Cock Blocks
We’ll close out Part 2, and I will leave you with this story. Honestly, this is one of my favorite stories of all time, and it is literally something I close with in a majority of my standup comedy sets. However, tomorrow and Part 3 is gonna be ridiculous, so strap in.
January of 2013. Again, this is my worst year I’ve ever had. I was fucking pathetic. I had just broken up with my girlfriend. A few weeks later I was drunk and sad and started texting her. One thing leads to another, and next thing I know we’re sexting. Background, if you haven’t already noticed, I’m extremely awkward with women.
Now the reason this story is so sad is because it’s so so true. So 15 minutes in she sends me a naked pic. And, for whatever reason I decided to switch up my response from the “Oh yeah?!” I had sent like 27 straight times.
Sadly, for some reason, I decided to text, “Mmmmmmm.” Ya know, so she knew her vagina was like Campbell’s Soup good.
However, it did not go to plan because my cock block of an iPhone autocorrected…to “Mmmbop.”
Yep. We’re fucking 8 minutes in and you default to a fucking Hanson lyric?!
You wanna talk about a vaginal sham wow…
Other Fun Facts about me for Day 2 –
My mother is a pastor
I was kicked out of Catholic School
And, I have paid actual money to see Creed and Ke$ha in concert.
I once showed up to an exes apartment hammered drunk at 3 am singing Cher’s “If I could turn back time” to win her back. It didn’t work.
That’s all I have for Part 2 of my 30 for 30. I hope you enjoyed it, and I appreciate all the reads and laughs from all of you up until now. I will say this though…tomorrow will be my 30th birthday, and I am going to share my most amazingly horrific stories and mishaps such as: hooking up with a cancer patient, shaming an elderly woman after she fell, and how I lost my virginity. Get excited.