Barstool Chicago Awkward Moments Draft Grades

Round 1 Pick 1: Sending a Text Screenshot to the Person, Eddie

Very good, extremely awkward. It is something that is impossible to cover up and it is just terrible. Luckily I've never done this, but I know how awkward it can be. 

Grade: A

Round 1 Pick 2: Thinking Someone is Saying Hi to You, Tommy

Eh, this isn't that awkward to me. So someone accidentally says hi to you, it's awkward for five seconds but you just walk away and move on. I think it has a spot in the draft but was taken a bit too early. 

Grade: B

Round 1 Pick 3: Handshake/Fist-Bump Mixup, Carl

Very similar to the pick before it. Yeah, it's awkward, but unless you're Jake Marsh hugging Eric Musselman, it is something that you forget twenty minutes later. It also isn't really that awkward to me, you can just laugh it off and move on. 

Grade: C

Round 1 Pick 4: Asking for a Plunger, Chief

Yup, insanely awkward. Once you do this everyone knows you took a massive dump and that it is just sitting there as you scramble around to fix your mess. Then just plunging the toilet is awkward by itself. I think this was a very good pick from Chief. 

Grade: A+

Round 1 Pick 5: Watching a Sex Scene with your Parents, Dave

Yeah, this is pretty awkward. I would say it is even worse when it is a noisy sex scene. It isn't too often, but sometimes there is a little bit of a noisier sex scene and not just one with music in the background, which is extra awkward. Great pick from Dave.

Grade: A

Round 2 Pick 1: Walking side-by-side with a Stranger, Dave

This is like a little awkward, but not worthy of being sixth overall. It is very easy to get out of this situation too, so I don't love the pick right here.

Grade: B

Round 2 Pick 2: Someone Getting a Card Declined, Chief

Yup, great pick from Chief. Getting your card declined is incredibly deflating. You know you have enough money, but the reader just doesn't work. Everyone in the whole store thinks you have no money and you just have to sit there like a shmuck. Great pick.

Grade: A

Round 2 Pick 3: Asking a Non-Pregnant Lady when she is Due, Carl

Great pick. I really don't have a lot of commentary on this, it is just an incredibly awkward situation. 

Grade: A

Round 2 Pick 4: Someone Making you watch an Unfunny Video, Tommy

Underrated awkward moment. When someone shows you a "funny video" you trust them. It is most likely your friend who you trust to be funny. So you start watching the video, you stand there and wait for the funny part. They watch you, continually becoming more and more disappointed. You then try to cover it up with a smile and you say "oh yeah that was funny". But you both know. Great pick. 

Grade: A+

Round 2 Pick 5: Being at a Friend's House when their Parents are Fighting, Eddie

Yup it's awkward. Both you and your friend are trying to ignore it as they begin to yell. When it's finally over, your friend starts to apologize and you kinda just say "oh it's ok". You just don't know what to do. Very awkward. 

Grade: A

Round 3 Pick 1: Walking in on Someone's Stall, Eddie

This is pretty awkward but largely avoidable. You can usually see if a person is in the stall. However, if it does accidentally it is certainly awkward. I would rank it higher if it wasn't so rare. 

Grade: B

Round 3 Pick 2: Untimely Boner, Tommy

I don't understand why this was given so much shit, it is an incredible pick. The guys act like you just stop getting boners as you grow older. While you obviously get fewer boners as you get older, they still happen. So having a boner at the wrong time is incredibly awkward and very hard to cover up.

Grade: A

Round 3 Pick 3: Walking in on Parents Having Sex, Carl

Yeah it is awkward, definitely, But I feel like this never really happens. Most parents either don't have sex with their kids around or just don't have sex at all. It's a good pick, but for some reason, I just don't think it should be graded too highly. I mean idk. Whatever.

Grade: B

Round 3 Pick 4: Saying Goodbye and Walking in the Same Direction, Chief

Good pick. You kinda have to make a little bit of small talk on the way out, but like you've already done it. It is also weird to not talk because you know the person. It is just a hard situation to avoid. 

Grade: A

Round 3 Pick 5: Accidentally Farting in Class, Dave

Yeah, I like the pick from Dave. It is just awkward and really hard to make excuses for. 

Grade: A

Round 4 Pick 1: Guessing Baby's Wrong Gender, Dave

Eh this isn't super awkward. You just kinda apologize and go on with your day. 

Grade: A

Round 4 Pick 2: Accidentally Liking an old Instagram Picture, Chief

This is one where you have no way of hiding it. You just do it and live with it. It is so awkward and you will have a persistent fear if you do it. IDK if I've ever done it, but I may have once or twice. It is just so stressful and awkward. 

Grade: A

Round 4 Pick 3: Diarrhea at your GF's parent's house, Carl

This isn't terribly awkward. It happens to everyone and most people understand. I think the sound is really the awkward part, but overall isn't terrible. 

Grade: C

Round 4 Pick 4: Loitering Between Conversations at Parties, Tommy

Underrated pick. I'm not the most social guy, so if I am out and just in between convos it is awkward. You are either on your phone or just looking around for someone to talk to. I think this is so awkward because you are singled out and vulnerable. It seems like everyone is looking at you. Great pick. 

Grade: A+

Round 4 Pick 5: Watching a Stand-Up Comic Bomb, Eddie

This is a very different kind of awkward to the rest of the list. It is a second-hand embarrassment. You want to laugh, you really do. But there gets to a point where you are almost mocking the person if you try to laugh. I've thought about doing some open-mic night sort of things before, but this is one of my biggest fears. Very awkward and a very unique pick.

Grade: A

Round 5 Pick 1: The Day the Cut-List is Posted for Sports, Eddie

I like the pick. It really sucks, especially when your friend makes it and you don't or vice versa. If you don't make it, it sucks, everyone starts to say "oh maybe next year" or "Man you were the next guy to make it" and the pity is just so awkward because you know they don't mean it. I really think this is a strong pick. 

Grade: A

Round 5 Pick 2: Asking Someone for Money that they owe You, Tommy

I actually don't think this is that awkward. They owe you money, that is your money, just go and ask for it. It isn't awkward to me at least. 

Grade: D

Round 5 Pick 3: Leaving Porn Open on your Computer, Carl

This isn't awkward but more a dumb move. I mean yes it's awkward to do it, but like how dumb can you be? Just close out the tab. Either way, it is awkward but I don't love the pick because it is so easy to avoid.

Grade: C+

Round 5 Pick 4: Coughing during COVID, Chief

Yup. Yup. Yup. My school just lifted our mask mandate I guess three weeks ago and on my first day at the library, I had to cough really bad. I wasn't sick, some water just went down the wrong pipe, you guys know the deal, it's whatever. But, I was acting like I was diffusing bombs here trying to time my coughs and mask them, it was so awkward and difficult. Love this pick.

Grade: A+

Round 5 Pick 5: Joking about a Sore Subject, Dave

This just feels like a punching the clock kind of pick. He couldn't think of a pick so he just went really broad. I mean it is awkward, but I would've liked something a bit better from Dave here.

Grade: B

This is gonna be a close draft, Chief and Eddie have very good ones filled with heavy hitters, but I think Chief will be the king of awkward this week.

Predicted Winner: Chief

Predicted Loser: Carl