Anonymous Mailbag

Videos by OutKick

Charlotte McKinney, Kliff Kingsbury

It’s Tuesday, time for the anonymous mailbag. 

As always you can email me at and I guarantee anonymity on all your questions. 

Here we go:

“Avid mailbag follower here. I finally have a gem to contribute:

So, this weekend, I’m out with friends, and the guy I’ve been seeing for nearly a year sends out the ole bat signal (“come over” text at approx 2am) and I took him up on the offer. We had a great time. I’ll let you and the Outkick readers fill in the blanks here.

Some context: he’s a med student from a wealthy family and lives in his grandparents’ guest house in a very nice neighborhood. The grandparents spend most of their time at their other home in Florida, and he watches the main house for them while they’re gone. Kind of a weird situation, but I had never given it a lot of thought… until this weekend.

I had some obligations to attend to and was up and at ’em pretty early (7:30 on a Sunday morning) and called an uber to pick me up so that he could sleep in. As I’m about to walk out of the guest house, I have a moment of what I believe was truly ESP and I stopped and said “_____, are your grandparents here?” to which he responded “Oh my gosh yeah, do you see them through the window?”

I didn’t see anything – the big house looked dark and quiet. I could see a computer monitor in the house with a screensaver moving, which I figured was probably an all-clear for no one being up yet, and I exited the guest house.

I weave through the garden and around the corner of the main house to meet my uber and who do I bump into?

Grandpa clad in nothing but his boxers holding the morning newspaper.

I mean, we basically stepped on each other’s feet because no one was expecting the other and we were both looking down. Only words to escape his mouth?

“Oh my god.”

I calmly nodded, hopped in the uber, and sped away with my sex-hair head buried in my hands.

Two questions – who is the biggest loser in this situation? Me, who had to deal with the unbelievable level of awkwardness in the encounter, or the grandson who will inevitably have to discuss this with his grandfather/landlord? OR, bonus option: the 80 year old man caught in only his underwear outside? I’m leaning toward myself.

Secondly, what was the play here? I was in a dress and heels clearly from the night before. Should I have explained myself? Introduced myself? Made up a lie about why I was there? In retrospect, I am just giving extreme thanks to God that the uber was indeed right there and I didn’t have prolong the encounter to look around for it or call them.

Please grace me with your gay Muslim wisdom, and pray this does not happen again.”

The perfect play here is to say, “Good morning, you must be (insert boyfriend’s name here’s grandpa). I’m (insert your name here and shake his hand). My friend and I just stopped by to pick up your grandson for church. But it looks like he needs some more sleep this morning. Sounds like he and his med school buddies had a fun night. Hope to get to see you again soon.”



That’s a genius move. He’s an 80 year old man in his underwear. He doesn’t know about Uber. He thinks you’re getting picked up by a friend instead of an Uber driver. You’re dressed, presumably, decent after a night out at the bar in a dress and heels. No man, much less an 80 year old man, can ever decide what women are wearing and how appropriate it is for an event. (My wife has asked me ten thousand times what the appropriate attire is for an event and I can confidently say I have always been wrong.) As for your hair, you’re in your mid-20’s, your hair could be on fire and he wouldn’t notice if you’re in a dress and heels. 

So why couldn’t you be going to church early in the morning?

The even more genius play would have been to say, “We came to pick up my roommate for church, but she’s still sleeping in there. She had too much to drink and your grandson let her sleep over. He’s such a nice boy.”

Then you aren’t even involved. 

Bonus great option: Thank him for his military service as part of the greatest generation. Every old person fought in World War II. 

Once you had a thought that the grandparents might be home and see you, you needed to have a story prepared. It’s like in baseball where you visualize exactly what you’re going to do if the ball is hit to you. You always need a plan.  

As for grandpa’s awkwardness, I go out and get the paper every morning in my boxers. If people see me I just wave. It’s not like I’m standing in the front yard doing a dick helicopter. It’s just boxers. So I don’t think it’s that awkward for him.

And I certainly don’t think the grandson has any explaining to do. He’s in med school, meaning he’s at least 23 and a college graduate. If anything, if I was his grandpa I’d be jealous that he has twentysomething girls coming over. Congrats, the fact that grandpa was so shocked probaby means your boyfriend is faithful. Imagine how pissed you’d be if grandpa had said, “Again, with a new girl?! How does he get any work done at all?!”

“Oh wise PC bro slayer,

I’ve been married to a beautiful woman for 11 years. I feel like my single years was always a quest to get laid, always chasing tail. Then you find the one, right? And you think you’re done, you’ve found her.

Only to realize 11 years later, you’re still chasing tail. But now it’s just the one. At least before I was doing things to impress girls, take them out, buy them stuff… But now I’m doing all of that + dishes, house chores and more. All still apart of an effort to get laid more by my own wife. I’m positive that I’m doing way more work and getting laid way less.

I feel like I have a Corvette in the garage but I never get to drive it.

Share some wisdom with me and your readership and help them understand that getting married won’t end the cycle of trying to get laid and falling short.”

“I feel like I have a Corvette in the garage but I never get to drive it,” sums up a married man’s sex life so perfectly. 

Especially in a Tinder age when I see single dudes banging chicks left and right and all they have to do is send like eight text messages and go buy drinks for one night. Here I am, changing diapers, putting kids to bed, taking out the garbage, working my ass off to make lots of money, buying cars and clothes, and spending the goddamn GDP of Moldova on spin classes, and it’s all in an effort to get my wife to sleep with me.

I really did think all the work chasing sex was over when I got married.

Boy, was I ever wrong. 

“Like 100 percent of your readers did, as soon as I finished reading the mailbag last week I went over to PornHub and watched the video of the girl in glasses. This girl is hot! The ex-boyfriend should be proud that his buddies are beating off to something that he used to hook up with. The sad part is if not for you recommending the video I probably never would have watched it because of the rating that it had. At the time I’m writing this email, it has nearly 16,000,000 views and a 77 percent rating. I have a rule of thumb that I don’t click on videos that are less that 80 percent with at least a few million fews. I’m in my mid 30’s, married, and a father of two. I don’t have a lot of time to surf PornHub looking for good videos. I need to be able to log on and take care of business without a lot of wasted time. Are my standards for which porn videos I watch too high? Have I been missing out on great 70 something percent porn and not realize it? Thanks in advance!”

The PornHub rating system truly baffles me.

I pick my porns entirely based on my perceived ranking of the hotness of the girl in the screenshot. The man has zero impact. Admittedly this isn’t a fool proof method, but it’s something. So I’m sometimtes blown away that a video of a really hot girl having sex can have a rating in the 70’s. It’s downright insulting to me. You’re telling me that this hot girl having sex is only a C rating in your book? Do you kids know that I used to jerk off to scrambled screen Playboy when I a teenager? A sideways blue boob was gold. 

Kids today are so spoiled. 

Anyway, then I think about who rates a porno movie on a free porn site. I’ve never rated one. Have you guys? Who rates porno movies on free porn sites. If I was single my Tinder profile would say, “Never rated a video on PornHub.”

In fact, short of a felony conviction can you think of a description that would make you more nervous if your sister or daughter was dating a new guy and he was described as, “the kind of guy who rates a lot of videos on pornhub.” RUN AWAY FROM THAT MAN NOW!

“I read your article last week about the divorcee who thinks a hot Asian stipper wants to “date” him, and it turns out I have a very good friend who was in this exact situation. Buddy got divorced, hit up the strip clubs and a smoking hot stripper began talking with him, like a normal person. She actually asked him out to dinner. This was two years ago. He asked me what I thought, and as a married man with a kid, I told him that he owed it to all male humanity to go out with her.

He took her to an expensive dinner, then back to his place where he nailed her like he was 17 again. Here’s the kicker – when she got up to leave she told him her fee was $400. While my buddy was caught off guard and slightly shocked, he paid her. Since then, he meets with her like clockwork every two weeks. No dinner anymore. She just comes over, he gets what he wants; and she leaves. I told him it was illegal and his response was that paying her $400 is way cheaper than dinner/cab/drinks and the drama from dating someone. He still has other chicks on the side; but every two weeks he basically gets a smoking hot porn star to come to his house and do whatever he wants. It got me to thinking, is the best setup possible? I mean, he gets hot sex and doesn’t have to get bitched out when he wants to go fishing. Also, what would the average guy be willing to pay for hot, drama-free sex every other week?

Love to hear the input from a sexist homophomic gay Muslim.”

Everyone pays for sex, some just do it with cash.


That’s honestly what I think, prostitition should be completely legal between consenting adults. Think about how strange it is that our tax dollars go to pay women who pretend to be prostitutes busting guys who are trying to pay them for sex. Personally I think being a fake prostitute is a much less honest job than being an actual prostitute.

“What do you do for a living?”

Fake prostitute cop: “I pretend that guys can pay me for sex, but then instead of having sex with them I arrest them and put them in jail.”

I mean, fuck you. That’s the worst cock tease of all time. Adding insult to injury the poor bastard you’re arresting has helped pay for your job with his tax dollars.

So instead of making prostitution legal, we use our tax dollars to pay women to be fake prostitutes.  

I believe legalizing prostitution would actually be the best way to save underage girls and catch illegal sex smugglers because it would allow law enforcement to focus on actual crimes. If two consenting adults want to engage in sex for money, why should the government be involved in stopping that? I don’t want my tax dollars going to pay fake prostitutes. 

Anyway, what’s amazing to me is she set the rate at $400 because that’s the efficient market rate. Which seems insanely cheap to me. That’s like two meals with alcohol. That’s all it takes?!

This reminds me of the great Charlie Sheen line when one of his friends couldn’t believe that he paid for sex. Sheen said, “I don’t pay them for sex, I pay them to leave.”  

“So after reading a few of your mailbags and really figuring out that you are in fact my hero in the sports community, I felt it obviously necessary to ask this question that I have had to try and figure out numerous times being a broke college student who always forgets to buy toilet paper. So anyway, you are hanging out etc.. And realize crap, I have to poo but you realize you have no toilet paper. To your dismay you go into the kitchen are out of paper towels and napkins as well, but at this point there’s no holding the rockets that want to come out of your bum, so you rush to the toilet. Now you’re sitting there trying to figure out what to use to wipe… What is the optimal solution here?”

Hop in the shower after you go to the bathroom. 

Problem solved.

Going straight to the shower after a poo is incredibly underrated. If you can time your poo in the morning right before you go shower, it’s perfect, you don’t need to use toilet paper at all.

Try it. 

“I’ve been married for 6 years and my wife’s pretty hot. That’s not germane to the story at all, but just keep that in mind. So Sunday morning, we were laying in bed, kind of half asleep, and she got up to use the bathroom. When she did, I decided to be respectful and rip a huge fart while she was out of the room. The problem is, I gambled on a fart and lost. I straight up shit the bed. I lay there, eyes wide, paralyzed in my own excrement. I did not want her to know.

My reaction was poor. As she came back in the room, I screamed at her, “WHAT ARE YOU DOING TRYING TO WAKE ME UP GETTING IN AND OUT OF BED, SO DISRESPECTFUL, WHO LIVES LIKE THIS?” She looks at me like I’m crazy and snaps something back. At that point, I get up and rip the sheets off the bed and storm past her in the hallway. She asks what I’m doing and I say, “Washing the sheets, SOMEBODY’S gotta keep this house clean since you don’t.” I never clean and she always cleans.

She gets offended by this, as she should, and starts to get sassy. I say, “I can see you’re set on ruining this day; I may as well have a day to myself,” stormed out of the house, caught the 13 Hours matinee at the dollar theater, and hung out at friend’s house and drank the rest of the afternoon. I’ve been out of town for work since then and we haven’t talked about it; we’ve barely spoken in fact and I know she’s still pissed at me. I don’t want to admit that I’m wrong or that I shit on our 800 thread count sheets.

How would you handle the situation going forward?”

I would admit that I shit in the bed and was so ashamed by it that I acted like a total asshole. 

In situations like these, brutal honesty is the only answer. 

“First off this mailbag is the only thing that gets me through Tuesday’s at work, I have a question about a situation I feel like a lot of dudes have been in before. One of my friends, we’ll call him Steve, is dating a girl who we I’ll call Kate. Steve is constantly bragging about the fact that he only dates 8’s and above and is constantly referring to Kate as the hottest girl he’s been with, saying she’s a 9. Kate is a hard 4.2, just absolutely disgusting, wouldn’t touch her with Bin Laden’s dick. My question is, is it my place as a friend to let him know that his girlfriend actually looks like she’s a mix between Shrek/Sloth? Or do I leave it alone and continue to let him live this massive lie?”

If you brag about how hot your girlfriend is she probably isn’t that hot. Because if you have a really hot girlfriend then there’s no need to brag. Everyone has eyes.

Your friend is bragging either because he likes this girl so much he has awful taste and actually believes it — which is kind of charming — or because he secretly knows she isn’t very attractive and is begging for your validation. Your silence is confirming his fears.

You don’t need to tell him anything, just stay quiet.  

“Have you ever accidentally masturbated to pictures of your mom when she was younger? If not, how should I handle this?”

Unless I just found out that Pamela Anderson gave me up for adoption when I was six months old, I would cut off my penis if this happened.

More seriously, the only way I can see this being possible is if your mom did naked magazines before you were born, you just found a stash of your dad’s old porn, and you didn’t recognize your airbrushed mom in the pictures.

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.