Anonymous Mailbag

Videos by OutKick

Charlotte McKinney, Kliff Kingsbury

It’s Tuesday, time for the anonymous mailbag. 

Here is yesterday’s Outkick the Show with my interview of former Tennessee coach Phil Fulmer and our discussion of Peyton Manning’s retirement. 

On to the mailbag:

“Longtime reader of Outkick, way before the Fox Sports days, used to listen to 3HL everyday when I was in high school in Nashville. I’m even a member of your political party, “The Radical Moderates.” Now I’m a freshman at Oklahoma. Our spring break is next week. I’m in a fraternity and we have recently come across a very serious problem. Our chaperone — we need someone over 25 to sign for the keys to our house — for the trip bailed because he is having back surgery. We’ve pretty much run out of options for a chaperone. While thinking about who could possibly chaperone a group of 20 college freshmen, I thought about none-other than the Steeplechase king, Clay Travis. We have even gone as far as posting on Craigslist. While I think that is an okay idea, I would rather not sleep with one eye open in fear of a random 33-year-old Northwest Floridian man sneaking in my bed. We would like to make a proposition to you. We will pay for all your food and alcohol for the week if you come on the trip. We would love to have you join us in our conquest to #SaveOurSpringBreak.

See you in Destin.”

I love this idea because writing about being the 36 year old Spring Break chaperone for twenty college freshmen in a fraternity pledge class would be an incredible article for Outkick. Just a daily diary on the site would kill. In fact, every single one of you reading this right now is thinking that I have to do this.

There’s only one problem — I’ll be in Las Vegas for the opening week of the NCAA Tourney next weekend. So I can’t make it.


(But for Outkick readers who will be in Vegas, we’re going to do a meet up at some point over the opening weekend of the tournament. I’ll send out a Tweet and write about it next week on Outkick).

“I’m a college student at an SEC school. But I’m a virgin. I know. I’m shameful. I’ve been social since freshman year. Been the wingman to all my friends. But it hasn’t happened for me. I’m a 5th year senior who hasn’t missed a football or basketball game in my college career. I’m not antisocial. So what do I do? I graduate in May. Do I have a chance?”

If you’re a fifth year senior in college and still a virgin — and not by choice — I feel like you have to have really high standards or be very socially awkward, potentially both. So the first thing I’d suggest here is knowing your game, that is, what are you good at that you can use to be attractive to girls? More than anything else girls like guys who are good at something. It doesn’t matter what it is, playing the guitar, sports, painting, writing poetry, being a math genius, find your skill and magnify it. The only reason music exists is because guys get laid for playing music. The dude who invented the harp probably got so much cavegirl ass. 

If you don’t have a solid talent, that’s fine, then move on to more basic level talents: are you funny, are you nice, are you rich, are you smart, are you good at making conversation — you probably aren’t ridiculously good looking or you would have stumbled into sex at some point — basically what is your asset? You need to be self aware and assess yourself relative to other guys. Why are your friends having success and you aren’t? Basically, you need to sit down and pretend you’re about to go to the NFL Draft, make a list of pros and cons. Emphasize your pros and limit your cons. (Honestly, girls have this down to a science. Every girl knows how to emphasize her physical attributes and minimize her flaws. That’s why every girl on earth has an incredible social media profile pic. It’s literally the greatest photo ever taken of them in the history of their lives. Meanwhile most guys are total idiots about this sort of thing. It’s why so many grown men have social media profile pics in jerseys.)     

Once you’ve figured out what you’re good at, I would advise thinking about how to maximize the social situation to take advantage of what you’re good at. That is, find the social scene that magnifies your good attributes and spend time there. Finding the right scene for you will help to lower your social awkwardness. 

Finally, lower your standards.

If you haven’t had success in five years, it’s probably not the fault of the women, it’s you.

Good luck.   

“Since you were a prophet predicting Trump talking about his dick and the godfather of the term ‘good dick day’, I figured I’d tell you a legendary good dick day story to share with everyone.

There was a guy in my high school who was rumored to have a massive schlong. It was a small country high school and rumors like that get around. He played football and teammates who claimed to have caught a glimpse backed up the rumor but there were still skeptics. So one night at a field party, the schlong was brought up which proceeded into a gambling event. The over/under was set at 9.5 inches. After some convincing the guy was going to whip it out to end the bets. Being a country area, of course someone ran to their toolbox in their truck and grabbed a tape measure.

Everyone gathered around the hood of a car where the event was going to take place. It was getting fairly rowdy in anticipation for the reveal. The dude whipped it out, plopped it on the hood of the car and everyone went silent.

There was no need to measure and a measurement didn’t take place. Easily over.”

Dick. Mic. Drop. 

I love this, the excitement of all the party goers, some dude standing in a random country field taking bets on the dick over/under and then this dude throws his dick on the hood of the car and no one even bothers to measure.

It’s a literal dick mic drop.  

This should be a scene in a movie. 

“Please keep my anonymous, obviously. I’ve been seeing a girl for a little more than a month and had been debating whether to ask her to officially be my girlfriend, and was sort of freaking out about it to the point that I drafted (but did not send) you an anonbag question last week. She stayed over at my apartment this weekend for the first time, and I thought you’d appreciate the following exchange when she gave me a morning hand job:

Girl: “Blow jobs are reserved for… [doesn’t finish sentence]”
Me: “I want you to be my girlfriend.”
Girl: “What took you so long?” And then immediately gave me a blow job.”

Ah, romance. 

In five years this girl will be saying, “Blowjobs are reserved for my fiance.” And then she’ll get married and never blow that dude again. 

“I have a situation where I need advise from an old guy. One of my best friends has been married for around a year and half now, his wife was really cool before they got married, but now she sucks. She does not let him ever hangout with our friend group, and if she does she insists she needs to come too. Then when we do let her come she only wants to stay for around 30 mins then he has to leave.  

She gives him list of weekend jobs where he is having to do crap around his house from sun up till sundown, while she doesn’t do anything. I know my friend really well and I don’t think he is happy, but he is someone who would never say anything. All of our friends have talked about wanting to talk with him about it, and they want me to do it. I feel like would either go really well, or he would get really pissed. Should I talk to him? Is this what marriage is about or is my friend getting the shaft?”

This is what marriage is like. 

In all seriousness, this is a delicate issue, he may be miserable, but you don’t know for sure. And if he’s miserable and doesn’t want to admit it, he may tell his wife about you talking to him about being miserable and then she’s going to hate you until they get divorced. Or, worse, for the rest of their miserable married lives together.  

The one thing I would say to every single person who is married right now — and may be miserable and looking to save your marriage — DO NOT HAVE CHILDREN BECAUSE YOU THINK IT WILL MAKE YOUR MARRIAGE STRONGER. 

Having kids to make your marriage stronger is like lighting your house on fire to stay warm on a cold night.

Kids don’t make weak marriages stronger, they make it infinitely more difficult.  

“A buddy and I have been put in charge with planning a bachelor party for a friend. The catch is that two of his brothers will be ages 18 and 20, respectively. Some friends (not in the wedding party) suggested Windsor, Canada, but I’m not a huge fan of taking this thing across the border for what I’ve heard is a very ordinary scene. My co-pilot and I have discussed getting a lake house somewhere in Tennessee or the Carolinas and making it a great guys weekend with golf, booze, boating and potentially a shitty strip club nearby. I have no doubt this would be a great time and would be easy to coordinate, but don’t want to settle on this without some other ideas. I know this is right up the alley of the Outkick audience so I figured I would get your thoughts or hear any other ideas I may be looking past.”

If you’re going across the border, go to Montreal instead of Windsor. 

I’ve been to strip clubs in both cities and there is no comparison.  

But the lake house is probably a safer bet. Bachelor parties and passports is a potentially bad combination. 

“We used to have a roommate in college that was a little douchey, and became a complete ass once he started drinking. This roommate was very frugal and went as far as keeping a set of plastic silverware (spoon, fork, knife) that he would wash and re-use….plastic silverware. He kept this silverware on top of the desk in his room. After a night of his douchiness, we would often take this silverware and wipe it all over our butt holes or ball sacks. The joy in all of this was watching him slurp and suck on this silverware that night as he enjoyed his bowl of Ramen noodles.

This roommate to this day has no idea that he was eating our ball and ass sweat for two years. He is a huge Minnesota sports fan and the rest of us are Wisconsin fans. There are usually insults exchanged during Packers/Vikings match-ups. I have come close to telling him this after the recent Vikings victory over the Packers. He is also a huge fan of Chris Kluwe…

My question is, is this something we should take to the grave, or should we expose it to him when the time is right? Looking for advice from someone who is used to putting things in their butt hole like the gay Muslim you are.”

Save it until the perfect moment.

Also, be careful, PC bros will argue you should be charged with sexual assault for this. 

“My wife was sick the other day so naturally my sex request that night was shot down.

Her “Leave me alone. I’m sick.”

Me: “Doesn’t bother me!”

She looked at me like I was insane.

That got me thinking….

How far would a normal late 20s-mid 40s married guy with a couple of kids go for consistent 3-4x a week sex?”

I have zero doubt that the average married man would pay his wife 20% of his take home income to guarantee sex four times a week. Some would pay more.  

The tough thing here is, of course, calculating how much the average married man is already paying for sex.

We asked this question a couple of weeks ago, without sex existing how many men ever get married? A tiny percentage, right? If you doubt me, think about what you would say if your buddy and his male roommate were great friends and they decided they wanted to room together forever and they were going to have an official ceremony that forever locked their financial status together. And if one roommate decided he didn’t want to live with that roommate anymore, he’d have to give him half of everything he owned. 

You’d say that was the dumbest financial decision you’d ever heard of, right?

Welcome to marriage. 

Every man is already risking half of his assets for sex. If anything, just paying for sex every time would be infinitely cheaper — and less risky — than getting married. Risking a little bit more than you’ve already risked for guaranteed sex four times a week? It’s a no brainer.    

“The multitude of monotonous and redundant Oscars Sunday night – plus the subsequent overnight ratings disaster – got me thinking, why isn’t there an Oscar category for “Best Topless Boobs in a Motion Picture?”

And when the inevitable PC Bro response comes, saying how degrading that would be to women, tell them we’d be happy to concede to a “Best Shirtless Man in a Motion Picture” category as well. What would PC Bros say then? After all, they’re all about gender equality, right?

The speculation and discussion leading up to the winner being announced would be enormous, which, of course, would be amazing for ratings. And how bout the unintentional comedy of the ensuing acceptance speech? “I’d like to thank my mother for passing on her glorious bosom to me and my husband for giving me the blessing to bare all!”

So because PC Bros would make the Oscars too big of pansies to embrace this, somebody, somewhere should hand out this award. And even though your gay, the Clay Travis Disney princess hotness rankings have made you just the person to do it! So who would be your pick for this year? What about all time?

And how much would fame go into your decision-making process? For example, if Jennifer Lawrence went topless and her boobs are a 7 and a B or C level actress went topless and her boobs are a 10, would the unknown actress win or would Jennifer Lawrence win because a topless scene with her would be a much bigger deal? Would considering fame destroy the integrity of this prestigious award? If not, what’s the lowest boob rating you’d go with for an A level actress to beat a lesser-known actress’s 10?”

Basically what you’re pointing out is the vast middle ground between the AVN awards and the Oscars. 

The AVNs give out awards for best blow job and best orgy and the like and the Oscars give out best actor and actress awards. But there’s a fertile middle ground here, right?

It’s making me think we should have a yearly Outkick Awards. We make up our own categories and give out an Outkick Award to the winners. It’s like the ESPYs for people who aren’t pussies.

I love the idea of creating our own board of voters and sending them movie clips to decide who had the best dick in a major motion picture in 2016. We’d have to retain our own accountants to keep the awards a secret. And then can you imagine who we could get to present the awards? 

To answer your question, Alexandra Daddario from “True Detective Season 1” has the best topless scene in the history of any movie or TV show.

This is non-negotiable. 

Send your anonymous mailbag questions to 

Written by Clay Travis

Clay Travis is the founder of the fastest growing national multimedia platform, OutKick, that produces and distributes engaging content across sports and pop culture to millions of fans across the country. OutKick was created by Travis in 2011 and sold to the Fox Corporation in 2021.

One of the most electrifying and outspoken personalities in the industry, Travis hosts OutKick The Show where he provides his unfiltered opinion on the most compelling headlines throughout sports, culture, and politics. He also makes regular appearances on FOX News Media as a contributor providing analysis on a variety of subjects ranging from sports news to the cultural landscape. Throughout the college football season, Travis is on Big Noon Kickoff for Fox Sports breaking down the game and the latest storylines.

Additionally, Travis serves as a co-host of The Clay Travis and Buck Sexton Show, a three-hour conservative radio talk program syndicated across Premiere Networks radio stations nationwide.

Previously, he launched OutKick The Coverage on Fox Sports Radio that included interviews and listener interactions and was on Fox Sports Bet for four years. Additionally, Travis started an iHeartRadio Original Podcast called Wins & Losses that featured in-depth conversations with the biggest names in sports.

Travis is a graduate of George Washington University as well as Vanderbilt Law School. Based in Nashville, he is the author of Dixieland Delight, On Rocky Top, and Republicans Buy Sneakers Too.