Anonymous Mailbag

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Charlotte McKinney, Kliff Kingsbury

It’s Tuesday, time for the anonymous mailbag. 

The questions have been great lately, but for new readers, I guarantee anonymity on all emails to the anonymous mailbag. So send your questions to

Here we go:

“The date was January 12, 2016. Alabama met Clemson for the National Championship of college football. Myself (an Auburn fan) along with several other Auburn fans gathered together at my place to watch possibly our two most hated teams battle it out.

Halftime rolls around and we are completely disinterested in the game, so we are thinking of things to do that could entertain us more than the football game. If you remember, by this time the Tennessee Lottery Powerball had climbed north of a BILLION dollars. So we did what anyone would do and headed just past the state line to buy lottery tickets (Alabama does not currently have a lottery).

On the way we all shared with each other what we would do with the winnings if we somehow hit it big. Once we got to Randy’s Quick Mart we left the girls in the car and me and my friend went in to handle the business. We bought several tickets and then decided to do a few scratch-offs just for fun. Of course we didn’t win anything, so we started to head back to the car when I said to my buddy, “Hey lets do one more scratch-off apiece.” I scratched mine off and didn’t win. I look over and my bleeping bleeper of a friend hit 200 thousand on a 5 dollar scratch off. 200 GRAND. I was in disbelief. Still am actually.

On the way home he offered to take all of us to the Auburn opener against Clemson with part of his winnings. Football season is soon upon us and my friend hasn’t mentioned the game once.

So I have a few questions. Do I ask him about paying up on his promise of taking me to the game or just let it go? Should I feel entitled to at least some small payout since he wouldn’t have won it without me pushing him to buy one more in the first place? Oh and one more thing… HE’S A PREACHER!”

He’s 100% obligated to take you to Clemson-Auburn.

He won $200k on a scratch off lottery ticket because of your suggestions and then he told everyone with him, while still overwhelmed by his good fortune, that he was taking all of you to Clemson-Auburn.

Preacher or not, he’s a real asshole if he doesn’t do it.  

Tickets right now aren’t even that expensive. You can get in for $150.

I wouldn’t expect him to pay for hotel rooms or anything, but he should definitely buy you guys tickets and go celebrate his winnings with all of you. 

Keep us updated on how that conversation goes. 

Don’t let him welch on this. 

“A few months ago I was coming home from a business trip in Thailand. Sounds terrible, right? It wasn’t. Anyways, I had gotten a few massages while I was over there and absolutely fell in love with them. And the price. Seriously, $5 for a massage? Sign me up every damn day.

Fast forward to when I come home. I decide one afternoon to go to a local establishment that’s offering Asian Massages. I walk in, pay the lady and then head back to the room where my massage is going to be happening. My provider comes in — very attractive middle aged woman — and she begins to talk and give me my massage. Everything was good, not touching or anything too unprofessional. Until it’s over. I stand up, thank her, and she walks over and proceeds to tell me she missed a spot. We can all guess what happens from there — I’m a guy and if an attractive woman is going to grab me by the balls — literally — I’m going to let it fly. And it did.

Fast forward again to this past week where it’s been about a month and a half since my massage spa experience. I’ve been dating a new girl, Asian, and she wants me to come and meet her family before we head out on a mini vacation. As we talk about it she shows me a picture of her family and they look great…especially her mom…WHO WHEN I LOOK CLOSER IS THE WOMAN FROM THE MASSAGE SPA.

So, what’s the play here? Do I pretend it never happened and act like everything is cool when I meet my girl’s parents? Will she even remember me? How do I shake her father’s hand?”

If true, this should definitely be in a movie. 

How would I handle this? I would make an excuse not to meet her parents right now. If you’ve only been dating for a little while, why do you need to meet her parents this soon? Push it to around six months before you meet her family. Assuming her mom gives happy endings to lots of guys, the odds of her definitively remembering you six months later are low. 

I’d also contemplate adding a beard — or taking one off if you already have one — in an effort to disguise yourself. Totally changing your hair style isn’t a bad move either. Basically, you have to treat this meet the parents moment like you’re an escaped prisoner. 

Working in your favor, who’s the mom going to tell about this? 

Just don’t go back there ever again, clearly. 

Good luck. 

“I am a faithful follower of the mailbag and I really need your advice. I am a happily married man and father of 2 beautiful young kids. Last night I really messed up. I was out with a group of friends and we were all pretty buzzed and to make a long story short I ended up in the backseat with a lady that I know just a little bit and getting a blow job from her. I don’t know what got into me, it was like I just lost my mind for a couple of minutes.

What is my play here? I feel very guilty about it, but if I tell my wife it could destroy our marriage. Do I learn to deal with the guilt and make sure it never happens again?

Your advice is greatly needed.”

You should keep your mouth shut about this and move on with your life. 

Seriously, just pretend it never happened. 

Right now some of you are jumping up and down screaming, “YOU HAVE TO TELL THE TRUTH!”

Not when you’re married, you have two kids, and you get a blow job from another woman in the backseat of a car, you don’t.

If you tell the truth the best case scenario here is your wife forgives you and for the next several years your life is miserable because she doesn’t trust you any time you leave her sight. (Which, to be honest, seems pretty fair.) Worst case scenario you get divorced over a drunken blow job in the backseat of a car.

I don’t like either of those situations.

This probably goes without saying, but when you got married you decided to give up blow jobs, from your wife or any other woman.

Sorry, that’s the deal.  

“Married mom of 2 under 5 with a serious life quandary.

Since everyone in Williamson County (Nashville, TN suburb) appears to have outdoor TVs in one shape/form/fashion nowadays what’s your stance on adult programming on these. Not just Skinamax level stuff, but, for example, I was sitting outside tonight and wanted to flip on “This is 40” and all of a sudden had a moment and thought maybe not a great idea. I just turned 40 and love this movie for all the truth it speaks to people that have been married for awhile and have kids and you know, survived. However, I also realize the retired couple next to me on one side and the young family on the other with like a 1 year old, while not in direct line of sight of the movie, could probably hear it. So, they may not appreciate some of the humor I find so relatable. We live in the land of 1/4 acre lots where you have to spend a small fortune in arborvitae (sp? – my landscaper does that stuff!) to get some privacy so while we have some privacy, it’s still for public consumption.

Now we already christened the deck and patio more than once after too much wine but should I be watching R, or worse, rated movies on the deck? I’m thinking the answer is no, but your wise counsel is always appreciated.

PS: I did go with the Olympics, for now :)”

I think R rated movies are fine, but I wouldn’t watch porn out there or soft core porn on Cinemax either. 

Sure, you can argue that it’s your home and you should be able to do anything you want on your property, but if your neighbors can easily see into your backyard you have to assume everything you do back there is public. Especially since a TV, with bright flickering images and sound, naturally draws the neighbor’s eyes.

Plus, if you’re watching porn, you’re planning on doing something sexual, right? (Would there be anything creepier than a dude who just watched porn with no intent to jerk off or have sex with his partner? Like who watches more than 15 minutes of a porno movie in one sitting? You can’t trust these people.)

So I’d move porn viewing and Skinimax films inside. 

As for casual nudity in R-rated films, I wouldn’t worry about that. We have an outdoor TV and I watch sports out there quite a bit because when the weather is good, it’s like having a tailgate at your own house. I’ve watched “Game of Thrones” out there too, but nothing any more risque than that. If someone really cares about the nudity that shows up in “Game of Thrones” that’s on them. 

An easy test is this, would you be comfortable watching this movie or show on an airplane? I’ve watched “Game of Thrones” episodes on an airplane and not thought twice about it. But there’s no way I’m watching a Skinimax film. 

I haven’t seen “This is 40,” but I’m confident it’s well within the bounds of acceptable viewing.  

“Looking for some career advice/perspective.

I’m a few years shy of 30, live in a major northeastern city, and have been working in sales since a week after I graduated college. After working for a small-ish, yet nationwide sales company for four years (I excelled and made between $100-150k between ages 23-25) I left about a year ago to start my own sales gig with a few guys, same industry. Overhead is low, about a 1k-1.5k per month to keep things going and to date this year I’ve already earned my highest annual income in my career. On the surface, things seem great. If I gave you a company spreadsheet, we’d be trending towards $1M in sales this year or a little less. All solid.

The problem? My income is based purely on my performance, no paycheck – and while I’ve earned to date in 2016 my highest annual income ever, just a few months ago when there was a dip in sales I had nearly no money to my name, about to be in the gutter. I turned it around like a machine, and literally within 120 days I have more money in my savings than I’ve ever had in my life. Mathematically, things look great. But can I continue to live like this where a bad quarter has me eating buttered pasta? I’m about to be engaged, responsibilities clearly to follow. If I went back to do my same job for a large corporation, I could make a similar income but the ceiling isn’t nearly as high. Running my own performance based company, my income has no potential ceiling. Scaling the business is the long term concept, hiring people and making money off of them and such.

Part of my gut says to explore alternatives, live safe, have a 401k and health benefits that you don’t have to pay for. The rest of me says to go for broke, build something and live the Clay Travis life, or bust. Best potential here is I can sit atop a sales company in ten years, coast and toast. The bottom is that I stall for a few years of the same $ range and eventually need to start a family and have the security needed, never reaching my potential.”

You’re in your twenties with no kids and no wife. Why would you take the safe alternative right now? I swear to god I want to strangle every guy or girl who is their twenties and talkes about their 401k. Really? A fucking 401k? If you are 23, single and already thinking about retirement, you suck. 

The most fun years of your life are right now, while you’re young and single. When you’re 65 years old and finally get to hit that 401k money your life is going to be boring as hell. 

Right now you have a chance to develop true wealth. Worst case scenario you can always go back to the safe lifestyle of being an employee of a larger company. Best case scenario you could make millions. 

I just don’t see a downside here. 

You’re not going to go hungry, especially not now that you’ve been smart and put aside a decent sum of money to protect you in the event of a downturn. (If you own your own business I think it’s smart to have access to a year or even two years worth of your expenses that you can access. Not your full income, but just what you actually spend on your life. Once you’ve done that you have a decent amount of peace of mind.) 

If you could go two years without making a dime and you and your family would be fine, it’s hard to imagine a situation — absent a horrible injury or illness — where you’re unable to make money for two years. 

My number one piece of advice to you young guys and girl out there is take risks before you have kids. 

Sure, you can take risks after you have kids, but it gets much more stressful. Hell, I started Outkick with a 3 year old and a baby less than a year old, but that was much more stressful for me than stopping the practice of law for a fall to write “Dixieland Delight.” I was only 27 when I wrote “Dixieland,” and, while I was married, my wife worked and we didn’t have many expenses. If “Dixieland” hadn’t worked out, I could always go back to practicing law. (Hell, I could go back to practicing law now if I wanted to, a law degree is a nice safety net. I’m not going to do it, but I could). 

Now I’m 37 with an 8, 5, and 1 year old. There’s no way I’d abandon a stable career to take the chances I took when I was 27.

So, don’t be a pussy, take your risks now and get rich.

You’ll thank me later.    


I have been a loyal follower of Outkick since the beginning. In fact, your breakdown of the Alabama couple by the cowpond sealed my fandom forever.

I am writing you from work, which is generally not ok, but since I’m the boss, I will take some liberties this morning.

As with others from Anonymous mailbag, please keep my identity private, as my comments may not be universally welcomed.

I have been a superintendent of schools in (Big Ten state) for the past fifteen years. I have served very wealthy, suburban big city school districts, and rural poor districts.

I have almost always agreed with you and your opinions, but I felt compelled to write in on your take on the guy who was struggling with whether or not to move to a better public school or attend private school. I think, no, I know, you got it all wrong.

For all the readers out there, if you are worrying about your child’s academic career, please just know these two facts: the top two predictors of a child’s academic success are the mother’s level of education and the amount of books present in the home. If you have over 500 books in your home and your mother graduated from college, your child’s educational future is fine regardless of what school you attend.

I am often amazed that people don’t seem to see that when academically motivated parents move into the same neighborhoods, then those schools are academically successful. That success is then attributed to the school. Really? Are people that stupid? If Mike DuBose coached the AFC all-star team to a victory over New Mexico State, would he suddenly be a good coach? Of course not. But in schools, parents often assume that good test scores equals good schools. It has much more to do with the fact that that school is inhabited with students whose parents actually care what happens to their child.

Please take it from me. When looking for a school, understand that it almost doesn’t matter at all what elementary school your child attends. You, as parents, can help your child through school in elementary school. If you demand that your child is attentive, inquisitive and respectful, they will do just fine.

When looking at Junior High and HS, I would just look to see what types of elective courses and extra-curricular opportunities are available. This way, your child can find what interests them and have a happier educational experience.

My children went through school in both the affluent suburbs and poor downstate school systems. They did fine in both. In fact, my children were at the top of their class in both schools.

Clay, I am counting on your to help get out this message for me and all educators. Please stop this madness (of which you are currently afflicted). Parents…raise your children to be curious academic risk-takers who love to learn. Quit stressing so much about which school will help them get into college. It’s really your job anyway.”

I understand all of this, but I think peer group and culture of a school does matter a great deal.

Plus, if your kid is smart, it doesn’t take much to be a smart kid at most schools. I didn’t have to push myself at all from K-6, especially not fifth and sixth grade. And I was one of, if not the smartest, kids in my elementary school.

But when I got to 7th grade at Martin Luther King, my education got turbocharged.

I give a great deal of the credit for my success — college scholarship, law school, and the like — to MLK. I think my 7th-12th grade schooling mattered more than my college or law school did because I doubt I end up in my college or my law school if I hadn’t gone to MLK.

Your advice, coming from the educational system as it does, is definitely well appreciated.

My advice remains, get your kid in the best school you can afford.

Send your anonymous mailbag questions to, anonymity assured.  

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.