Anonymous Mailbag

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Charlotte McKinney, Kliff Kingsbury


It’s Tuesday, welcome in to the anonymous mailbag — the most popular weekly column on the Internet today. (I’m not 100% sure this is true, but I think it might be. Who else shows up for 52 straight weeks a year of columns on the Internet? No one.) We’re here to make work or school pass as quickly as possible.  

Schedule update: I’m headed to Houston to speak to a group tonight at River Oaks Country Club and next week I’ll be in Tuscaloosa on Wednesday. So if you’re an Alabama student or you happen to live in Tuscaloosa, we’ll have an Outkick meet up that evening. We’re also doing Outkick the Show live from Alabama’s campus on Wednesday before we head to speak to the class on campus. So that should be fun. 

Related: I’m getting quite a few requests of late to speak to groups. So if you want to try and book me to speak you can email (Warning: I’m not cheap. Especially if I have to travel. But I do have great hair and I’m incredibly entertaining.* 

*Compared to most other people you could hire to speak.) 

Yesterday’s Outkick Show was pretty spectacular. Especially the open where we discussed Steve McNair’s unique skill set. Here it is. 

Okay, here we go with the anonymous mailbag.

“While reading about the proper way for a man to wipe his ass in your Tuesday mailbag (fortunately, I have always employed the proper technique), I was reminded of a wiping quirk of my own. Back in the day, I noticed that whenever I would take a piss, I would notice some excess leakage as I had a drop or two of piss running down my leg – even after doing the “shake shake” for so long anyone who is around probably thinks I am jerking off. After putting up with the leakage for a while, I decided I would “wipe my willy” to get rid of the excess urine. Whenever I am able to employ this technique (it obviously isn’t an option when taking a leak in a urinal or outside), I never have leakage issues. However, when I have mentioned that I do this to my buddies, I get laughed out of the room. So I have the following questions – is my leaky dick an abnormality or is this common for most men? Is this something most men just deal with and are cool with having drops of piss leak down their leg? And, lastly, am I a freak for wiping my dick off after I pee?”

I think if you wipe your dick off with toilet paper after you pee, you’re a freak. 

I’m sorry. 

I mean, think about this, which would be weirder, you accidentally open a public bathroom stall and see a guy jerking off or see a guy wiping the tip of his penis with toilet paper? I honestly think the toilet paper pee wiper would be more of a shock. That’s how much of a freak the pee wiper is. 

“Question for the fabulous Clay Travis. I have been married over 10 years now and dated a 1-1/2 years before then. Love my wife, have 2 beautiful daughters, no complaints there. Well her parents live north of Nashville in a very prominent city, they have a nice size brick home on a few acres just off the main highway. We have a close relationship with them, see them a lot and we don’t live far away. 

Yet I have never once been inside their home. Not one foot. I’ve been on the property several times and stayed outside, but have never gone in. For the first few years we were together I thought it was just really strange, but after almost 12 years now, should I try and go in there at some point soon or just go for a Guinness World Record of longest a son-in-law has not gone in the in-laws house?”

This is beyond weird. So weird, in fact, that I don’t think your in-law’s actually live in this “nice size brick home on a few acres just off the main highway.” I think they’re faking you out and they actually live in a much worse place — potentially a trailer or crappy apartment — but either they or your wife are ashamed of where they actually live so they’re faking you out. Otherwise this makes zero sense. I can’t imagine a situation where someone has been married for over a decade, has a decent relationship with their in-laws — as well as grandchildren — and has never been in their in-law’s house. Never for Thanksgiving or Christmas? Hell, not for a single meal with your wife and kids? 

You have to ask to go inside to use the bathroom next time you’re in the front yard.  

I’m convinced it’s a fake house, they don’t really live there.


“As I was driving today I had an important question: What is the female equivalent of a good dick day?

I recently got a new hairstyle that has made my hair a lot more manageable and I’m able to style it much better, so my confidence has lifted. So as I was driving down the road thinking about how great my hair day was I wondered if this was the female good dick day? Both leave the person with extra confidence and a pep in their step (I’m assuming). The only difference is a good hair day is obvious to other people, and a good dick day is only enjoyed by the male and whoever he chooses to share the excitement with. 

Females can have good boob days I suppose – mine are the same all the time – but if that was a thing, it would also more than likely be obvious to others as well since size of breasts are kind of out there in general (unless added padding covers up the truth). So, I circle back around: What is the female equivalent of a good dick day? Inquiring minds want to know.”

I’m with you here — the thing about a good dick day is no one else really knows you’re having a good dick day. If a woman has a great hair day or wears the right bra, she can have a great boob day and everyone knows about it. (We’ve undergone a Manhattan Project of bras in the past twenty years. I’m pretty sure if I wore the right Victoria’s Secret bra every guy reading this right now would think I had perfect boobs. And that’s just not the case, my boobs are just okay.)

So here’s the answer: it’s a great vagina wax job. You get done with the wax treatment and you take a shower and when you get out and stand in front of the mirror you think, “Damn, my vagina looks really good today.”

Now most people won’t know this, but you will. You may even put on your bikini and go to the pool and lay out just because you feel so confident that you’ve got the perfect wax job going on. 

Bang, great vagina day. 


“So my buddies and I were having a debate about something via text. We all agreed with each other but we like to get outside opinions. Then one buddy texted “Mailbag that shit” so here we are.

The place where I work has a pretty lax dress code policy. Some people like to take advantage of this incredible policy more than others. One guy especially who sits next to me likes to wear a polo, khaki shorts, and beach flip flops. It’s so weird and shitty. I texted my dudes and they both agreed that this is weird af. Wearing flip flops in general can be questionable. Let alone wearing them to work with a polo and khakis. 

What is your overall take on flip flops? Is there ever a scenario where it’s not super weird to wear them to work? Has anyone ever thought someone was immediately a badass cause they were wearing flip flops? I’m hoping you absolutely shit on them and he somehow reads this and re-evaluates his life so I don’t have to deal with his flip flop bullshit anymore.”

You’re out of luck because I am incredibly pro flip flops. In fact, I used to wear flip flops into my law office and then switch to actual shoes — which I kept under my desk — once I was inside the office. That’s how much I love flip flops.

In my ideal world — which is, thankfully, most of my life — I wear as few clothes as possible all day long. 

For instance right now I’m wearing a tshirt and boxer briefs as I write at my desk. That’s it. That’s not abnormal for me at all. 

When we hired our nanny, my wife had all these detailed questions she asked about child-rearing philosophies and schedule flexibility and diet and then she turned to me to ask my questions and I said I just have one question: “How are you going to feel if I spend most of the day wearing my underwear around the house?”

Some of you think I’m making this up for comedic effect, but if you talked to our nanny now — who is fantastic and has been with us for a couple of years — she would say, “Yes, he asked me that question and, yes, he walks around in his underwear most of the day inside the house.”

One of the first things I do when I come home from a work event is take my pants off. 

So I gotta say, I don’t blame your coworker at all. If I had the option to wear shorts and flip flops to work, I would totally do it. To be honest, the fact that he’s going polo is probably more than I’d do, I’d go tshirt. That’s because I believe that any day you can wear a tshirt, shorts, and flip flops is a good day.   

My question I’d ask you, if you can wear flip flops and shorts to work, why aren’t you doing it? (Are you anti-shorts guy? Beccause I think anti-wearing shorts guy can go straight to hell).

“About 2 months ago, I was caught slipping and left a spank bank porn site open on my phones browser.  When my wife used my phone to check her Pinterest page, she was instead viewing a college orgy.  She was pretty pissed.  She said that it wasn’t the fact that I masturbate that made her so mad, but that I did so while staring at a bunch of girls that look nothing like her.  My wife is in her lower 30’s, has had 2 kids, but works out regularly and has a great body.  All that said, of course I jerk it to women that don’t look like her.  That’s what all men do, right?  

Anyway, this isn’t the first time this argument has come up.  Porn bothers her a lot.  She states how it makes her feel bad about herself and is very demeaning to women, etc, etc.  Couple of days later, I read an article in Men’s Health, about giving up masturbation.  I didn’t think it was possible, but the story told about how he had stopped masturbating for a decade, and how it had improved his relationship and overall life.  I thought about this for a couple of days and made the decision to give it a try.  At the very least it would be a test of will power. (Since my glory days of sports are over, I get my competitive juices flowing however possible)  I sent the article to my wife and let her read it.  I told her I would give it a try.  I think she was touched by the sentiment.  She pretty much jumped me then and there, and pretty much every other day since then.  Prior to this little experiment, we were having sex as much as 3 times a week and as few as once or twice a month.  Lack of sex had been a source of many arguments in the past, not anymore.  Shower sex, different positions, we are even having quickies while the kids are upstairs (hasn’t happened since before we had kids), afterward she will just give me a wink and tell me that was to keep me motivated.  I think giving up masturbation has been the best move of my post monogamy life.  I wonder if anyone else has ever tried this.”

This brings us to a fascinating question: married guys, would you give up porn to have twice as much sex with your wives? How about three times as much?

Your wife going to check her Pinterest account and finding a college orgy on your phone sums up the difference between the two sexes perfectly. She’s thinking, “Oh, I wonder what people think of my easter basket doilys,” and you’ve got college girls ski poling random dudes in the middle of an orgy on your phone. 

Too perfect. 

Here’s my question: why couldn’t you claim you were giving up masturbation and then get all the sex and still be able to masturbate too? Is that too diabolical?


Anyway, congrats to you and anyone else who wants to try this. Personally, if I gave up masturbation I’m not sure I’d have anything left to live for. 

“I’m a junior at an SEC school and recently this topic has come up for conversation with me and my friends: who should be paying for dates? Given all the talk of gender equality, equal pay, and perhaps the death of chivalry, surely only a gay muslim such as yourself can decide. 

In this day and age, I suppose girls feel obliged to offer to split the bill when the check comes – but apparently it’s a huge turn off if the guy accepts this offer. Why offer to do something if you don’t really mean it? Kind of a shitty move in my opinion. 

I’ve been raised on the rule of thumb that whoever asks the other person on the date should pay, or at the very least you should split/go dutch. 

What are your thoughts on this issue given the fact that it’s 2016 and not the middle ages, and chivalry may have taken on a different definition sometime in between given the women’s rights movement?”

See, I don’t think women should be able to play both sides here — if you’re a feminist who thinks that patriarchy and misogyny is ruining the world then you shouldn’t get free food and drinks and movies and whatever else when you go out. You should have to pay for half of the bill. That’s only fair.   



But women want to have their cake and eat it too. They’re all for girl power when it’s to their advantage, but as soon as a patriarchal society benefits them, they want that too. That’s total bullshit.  

Having said that, let’s be honest, hot chicks can get whatever they want. No one talks about hot girl privilege, but it’s the most powerful privilege — other than maybe male pro athlete privilege — in America today. No one is more privileged than a hot chick in America today. And the crazy thing is, hot chicks don’t even realize how extremely privileged they are until they get old and people stop trying to bang them. 

Hot chicks can get away with anything. Walk up to the most exclusive restaurant or club in America without being on the list? They’re in. Want to go out to a bar all night with only your i.d. and not a single credit card or dollar to your name? You drink — and eat — for free all night. It’s unbelievable what hot chick privilege can do. Again, the only comparable experience is “pro athlete privilege.” Pro athletes — male pro athletes, anyway, I don’t think there’s a WNBA privilege — can pretty much do anything they want too.

That’s why it’s always funny when pro athletes talk about how hard they work. Stop. Every lawyer, doctor and investment banker in America would kill for your schedule. You work hard for a pro athlete, which isn’t very hard at all. I roll my eyes every time I see a pro athlete talk about how hard they work. Dude, most of you wouldn’t last a day at an investment bank.   

Anyway, I’d definitely watch a reality show where hot chicks got put in fat suits. Call it privilege check.

(By the way, since we’re talking about privilege, I still want to be a rapper and have my stage name be “White Privilege.” This is the greatest rap name of all time. I can’t even rap and I just want the name. So it’s mine, I’m “White Privilege.” We need tshirts.)  

“I banged my good friend/roommate’s girlfriend. But this was before they dated. It’s super weird but I just let it go they appear to be happy.

So here’s my question. What is the degree of separation on knowing someone who has banged someone who you would potentially date? I feel like if you have to ask you already know the answer but what would you say the threshold is? I mean as long as she’s not a virgin she’s had sex with someone, you just have to live with that. I definitely think my situation you can’t do it. Curious to hear your thoughts.”


One of my friends dated another of my friends and before he dated he pulled the other dude aside and said, “Did you go down on her? I can’t date her if you went down on her.”

Here the big question is, does he know you banged her? If he knows, that’s fine. If he doesn’t know, you need to tell him. I don’t think it will change anything, but he just needs to be prepared for when it inevitably gets thrown in his face during an inevitable marital argument about him spending too much time with his friends. “Oh, you want to spend so much time with your friends? Well I banged (your best friend.) Did he tell you that?” 

Otherwise, if you get married in your late twenties or thirties there are probably people who the bride and groom have both banged in the wedding audience. Hell, some of them are probably groomsmen or bridesmaids if the wedding party is big enough.

I also think there’s a distinction between dating each other and casual sex, how long ago it happened, how many respective partners each person has had since, these things all matter. It’s a balancing test. 

“Please keep this anonymous as my friends and I have a question regarding a fellow colleague. Our friend group consists of mid-twenties college graduates/graduate students and one member of our group (who is 25) has a habit of attempting to date/hook up with much younger women, most often barely-18 year olds. This has been going on for sometime, as he has had the trend of doing this when we were in high school as well (Dating freshmen as a high school senior, etc.). 

While I enjoyed and believe your take on married men wishing they had taken advantage of getting laid more when they were younger, myself and the rest of our group find this particular pattern weird. We’ve been thinking about addressing this with him, especially since quite a few of these barely-18 year olds are still in high school(!!!!). We wanted your take on it: In your opinion, what is an appropriate age differential for hooking up with younger women, without it being weird/borderline predator-like? We’re strictly talking about the young, under 30 crowd here, not including older guys who have mistresses and such.”

If you’re in your mid-20’s and you’re dating a high school girl, that’s pretty weird. And also potentially illegal. Plus, let’s be honest, YOU’RE IN YOUR MID-20’s! You are surrounded by hot girls everywhere you look. You can go five years younger and date a girl who’s 20, or you can go five years older and date a girl who is 30. It’s impossible to ever have better options as an adult. 

So why would you want to date someone that young? It’s strange. You should talk to him. Plus, think of the poor high school guys trying to date that girl. How can you compete with a 25 year old with an actual car and an actual job and an actual place of his own? When you’re 17 years old a 25 year old might as well be forty. It’s ancient to you.

As for a general rule, I would say if you’re 25 or younger you can date all the way down to college freshmen. Sure, it’s strange to be dating a girl who can’t legally drink, but, let’s be honest, if she’s dating a 25 year old she definitely has a fake id. Plus, if you’re 25 and dating a college freshman the only rule is that she has to be much hotter than the average 25 year old you could date. That’s the only reason you’re dating her.

If you’re 26 or older I think you need to make it girls who are 21 and up.

If you’ve over thirty, you take whatever you can get. If you’re over forty, there are no rules.    

“Clay, I am the average guy with a pretty good life. I have been married for 10 years and with the same girl for about 13.  She’s 9 years younger than me (I’m 42) and I really outkicked my coverage. Only issue is that sex has been so so. Kind of boring but still get it 1-2 times a week even with a small child. Very few blowjobs or any extras. Just plain sex. Not complaining. 

Well….. a few weeks ago a friend of hers suggested some romance novels to read.  It was like a light switched flip and I am now married to a different person. My super conservative wife has turned into the most sex craved woman I have ever known. Blowjobs, non stop. Crazy sex every single day, she doesn’t even give me a choice. It’s insane. I’m actually needing a timeout but there are none. My poor little boy is even having to go to bed 30 minutes early so she has more time for sex.

My question is, will this continue?  Do I need to just keep her a supply of books to read?  Was it really this easy? I mean, have I stumbled upon a secret that other guys have known about but I’m just now finding out about? What I’m getting daily would be $300-$500 a night minimum in Vegas and all it’s costing me is a $9.99 digitally downloaded book once a week. I hope by sharing this that others will have the same success.”


This week’s mailbag has now turned into another edition of ways for husbands to get their wives to sleep with them. This week’s hypotheses: either stop masturbating or buy your wife trashy novels. 

I get tons of emails every week from husbands complaining about lack of sex from their wives. 

So I reiterate my marital advice to women everywhere — just bang your husbands more often. It’s better advice than the vast majority of you will receive from marital counselors and it doesn’t cost you anything.

Just do it.  

“This past weekend my wife and I went down to one of my fraternity brother’s weddings. The wedding was short and sweet and the reception was spectacular. While at the reception all the other brothers and I were shooting the shit and the topic of who else could have gotten invited came up. Another brother didn’t show up because his best friend since elementary school was getting married, so a legit reason. Then we found out that another brother did get invited but was nowhere to be seen. When talking to the groom later we found out he had texted him Wednesday mid day saying he couldn’t come. His text was “Hey man I didn’t get to sleep till 1 am last night and didn’t sleep well so I don’t think I can make it to your wedding.” Is this the worst made up excuse of all time? Or do you think he actually thought this was a legitimate excuse?”

Guys are really dumb. 

Like, no hyperbole, the average guy is incredibly dumb.

It’s impossible to have a worst excuse than this, but the more emails like this I get the more I think we should start an Outkick spin off site where girls just post the texts they receive from guys.

The number of guys who can actually read and write in a coherent manner is like 28% of the population. The other 72% are borderline illterate.


I’m sorry, ladies.

Outkick’s anonymous mailbag runs every Tuesday. Send your anonymous 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.