Anonymous Mailbag

Charlotte McKinney, Kliff Kingsbury

It’s Tuesday and as soon as I click publish on the anonymous mailbag I’ll be heading over to the SEC spring meetings in Sandestin. I’m not sure exactly what our Outkick the Show schedule will be, so be prepared for just a couple of minutes notice before we go live on Facebook and Periscope. 

As always you can send an anonymous mailbag question to me at

Okay, on to the mailbag. 

“My story is one mostly of a “Did I miss my chance at having a threesome/turning my wife and I into swingers”?

So it was New Year’s Eve a few years back, we went out to eat with my best friend and his wife and planned to stay at their house because we planned to get very drunk. I think we may have pre-gamed a little before dinner, had a few at dinner and came back to their house and were going to stay in the rest of the night drinking. Eventually just drinking and talking got boring so we started to play some board games.

The first one was some Awkward Family Photos game where you made up captions to the photos. Not awful, more fun since we were drinking but we decided to switch to a game called Dirty Minds. In Dirty Minds it takes every day objects and sexualizes them. This game was a hit, we’re all having fun and then my wife of all people says “Hey, let’s play this strip poker style. Get your answer wrong and lose clothes.” No one disagrees and we proceed.

My wife’s not a prude by any means but it was a little surprising that she’d suggest it. So we start playing and I think my wife ended up “winning” because the rest of us were naked where she still had her panties on but by then the game ended because we were all drunk and horny as hell so I dragged my wife upstairs and we broke in my best friend’s guest room.

I’d also like to say I am a grower not a shower so playing strip poker is nerve wracking. Are you supposed to be hard? You’re probably seeing some tits or maybe more so it’s not out of the question to get hard, or are you supposed to be under control so you’re not seen as some dude who pops a boner at the sight of a nipple? Well if you’re a grower, you almost have to be hard because if you’re not, they’ll think you got a small dick when you really don’t.

Anyways, after awhile I had to go piss and my friend and his wife had apparently decided to just fuck down on their couch instead of in their room upstairs next to the guest room. They must have been done because there wasn’t a whole lot of movement going on but as I headed back to the guest room, I did get a thumbs up from my buddy.

I guess my only angle of this to where there’d be a chance of cross pollinating is they obviously felt fine with banging out on their couch when we could have walked out at any time (like I did) to catch them in the act. I think my friend has always been a bit of a voyeur type because he used to pull down an ex-girlfriend’s top when swimming when I’d be around and find it funny so I don’t think he would every have much of a jealousy issue. The issue then becomes the wives. It’s one thing to play a game of strip poker when very drunk, it’s another to bang another person.

We haven’t had anything like this come up again between the 4 of us. My wife in college had her chances to make out with friends of hers but always thought kissing another girl was gross whereas my buddy’s wife has no issue kissing other girls. The nail in the coffin to me though is that my buddy and his wife have only had sex with each other, both were virgins when they got married and my wife has only had one other person besides me.

So there’s my story. There was never a real shot at this thing happening right?”

First, I love the dilemma of how much penis blood flow a grower needs to have while playing strip poker. Tough question here. Because once the blood flow starts, it’s hard to control. You go from a good dick day to awkwardly standing there with a full on erection pretty quickly. But the worst case scenario here, clearly, is you’re naked and your shriveled limp penis makes you look like a ten year old boy. You pretty much have to bang your wife in front of the other couple then just so they don’t start a whisper campaign about you having a tiny, baby dick. 

So how do you balance this out?

I think you just have to risk the erection. If it happens I’d make a joke and say, “Sorry, I didn’t know (other dude) was going to look this good naked.”

Now, as for whether you could have had group sex or swinging that night, the answer here is, as always, it doesn’t depend on what you or your friend want it depends on what the girls want. They control everything here. Your wife had the strip poker idea and the other girl was fine with it. The most you could do to orchestrate an orgy was to suggest, once nudity happened, a game of truth or dare. Then, like straight men everywhere, you could have immediately dared your naked wives to make out. I’m no expert, but if two naked women make out, that’s a one way ticket to orgy town.

Of course, the challenge here is these are your friends. Let’s say you all get drunk and have an orgy. Is it awkward in the morning? If I were going to have an orgy, I’d never want to see the people again. My ideal orgy would be like in “Eyes Wide Shut,” you walk in and there’s a ton of hot naked people in masks and then you leave and never see the people again.

Here you have relationships with each other, which could be awkward. 

The easiest way to figure this out would be to ask your wife instead of the mailbag. Maybe she’s wilder than you are and thinks you’re a pussy because you’ve never brought up that night again with her.

Good luck.    

“So two years ago I’m just finishing up with my senior year of high school. I was a pitcher for my high school team in a Big 10 city that’s known for its corn. Anyways as a very tall lefty I could throw hard — 86 miles an hour — and my ball had tons of movement, people couldn’t hit me. My only problem was that I sometimes lacked control and I was not very strong. This lead to me not receiving much attention from colleges, except for one. A JUCO in South Carolina that fed SEC/ACC schools with their players. I took a visit there and was told by the coach and everyone I knew that I had the potential to succeed there. The only person who didn’t believe I could do it was me. I ended up calling the coach and told him I would play only to pussy out and reverse my decision a week later and I’ve regretted it since.

Fast forward two years and I’m just finishing up my sophomore year of college at my Big 10 school. Lately however, I cannot seem to get the idea of me repursuing my baseball career out of my head. I have been practicing a lot lately for fun and I’m stronger now, I throw harder — up to 88 miles an hour on the gun — and I have better control. People still tell me I could play baseball if I wanted to.

Is it even fathomable for me to even consider calling the coach at the JUCO and asking if I can have a second chance? Or am I just being delusional? I know you get tons of questions so I’m not even sure you’ll respond to this but I ask that if you do it be quickly because I need some help. I have not been able to get this out of my head. Clay, what should I do?”

No matter who you are or what age you are, I’m always going to encourage you guys to pursue your dreams. Imagine you’re fifty and never make an attempt to restart your baseball career, you’d always regret it, right?

You’re a lefty who can throw almost 90 miles an hour and has decent control? And you’re only twenty? That’s a really rare skill set. I’d contact your JUCO coach again, but I’d also show up for open tryouts for your college team. If what you say is true, then you can probably pitch at your school. Which would be the best of both worlds, right? You get to stay in school and play without having to go anywhere. 

If you trust my opinion at all, you 100% need to pursue this dream.

Make it happen.

DO. IT.  

“Okay me and a few of my buddies were talking about weddings in the fall a few days ago and we were discussing back and forth if it is appropriate or rude to schedule a wedding on a Saturday in the fall? A few of them were dead set on having it in the fall and said they didn’t care about having it during college football.

I came back and said that’s fine but I would be checking my phone for scores and updates. They went on to say that they would be pissed if I checked my phone at the wedding and I was very confused by this because I, for one, would not care if one of my buddies looked at their phones at the wedding. Am I wrong for wanting to check my phone and should I just keep it up for one day or should they not care if I check my phone if they so choose to have it in the fall? We need the famous gay muslim to figure this one out for us.”

If you are a single man discussing weddings with your single guy friends and some of those single guy friends think it’s okay to have fall weddings and would be upset at you for checking football scores during their as yet unplanned and unscheduled fall weddings, then you need new friends.


If you’re a single guy you should only talk about three things with your male friends: sex, sports, and schemes to make more money. Anything else and you are wasting your male friendships.  

“There is a girl who I have been head over heels for since the moment I saw her, however for the first two years we knew each other, she has dated a guy that played football at an SEC school. Obviously being a D-1 athlete and getting all the pussy he can get, he cheated on her multiple times and she found out so they broke up.

While they were still dating, her and I would go out and get drinks, go to dinner, pretty much doing what couples do minus the sex. I have pretty much come to terms with the fact that I am in the friend zone, but is there any way to get out of the friend zone?”

So you do all the relationship stuff and this big swinging dick former SEC football player does the banging — while cheating on his “girlfriend” and having no real relationship obligations?



Lesson: No attractive girl bangs the dude who is the pussy. 

And right now you’re the pussy.  

Next time you’re out drinking tell her you like her, want to date her, and that you understand if the feelings aren’t mutual, but you can’t be in a pseudo-relationship with someone that you actually like. If she doesn’t have feelings for you then end the pseudo-relationship and move on to dating someone new.

Being unavailable is often the best aphrodisiac.

Also, when women say they want the “nice guy” they are lying. The nice guy is typically boring and lacks self confidence. Women don’t want to be bored and they don’t want a guy without confidence.

You can be nice without being boring as hell.  

“The other night we had some friends and their kids over. For the entire 2 hours before they arrived, we cleaned. Like clean as in a lot more than normal. Like my wife rolled a few towels perfectly and set them up neatly on the dryer along with a lit candle and fake flowers… As we were cleaning, the thought hit me – why do women do this and is there a male equivalent? I don’t wash and clean my truck if a buddy is hopping in to go somewhere, I merely grab whatever crap (toys, papers, books) is in the front seat and throw it in the back seat.

So what is the real logic behind all of this and what is the closest male equivalent?”

My wife cleans before the goddamn cleaning lady comes over. 

It’s the damnedest thing I’ve ever seen.

There is no male equivalent to this behavior.  

“Going to Disney World for a week in September with my wife and 4 year old son. We usually live like Clay Travis and stay in the suites which gives us a bedroom and him his own. Disney is so expensive my wife thought it would be fine to save some money and just get a regular room since we will not be in the room a lot.

Here is the issue, how do you have sex in a hotel room shared with your four year old? Are we perverts to do it while he’s asleep beside us? A friend suggested we sneak off to the bathroom but he’s sharp, he’ll be knocking on the door wanting to know whats going on. I don’t want our kid to grow up warped cause he saw mama and daddy having sex at the animal kingdom. This trip could be a sexually frustrated disaster. Any help?”

This email is peak dad. You’re going to Disney World in September and already thinking about how your vacation sex life is going to be impacted by the trip. Your wife is running around analyzing park schedules, park transportation issues and thinking about your son’s dietary and snack needs on this trip and you’re already worried about your sex life in four months. 

Great question for all the dads out there — what percentage of the money you spend on a suite is directly related to the amount it increases your sex odds with your wife? Why else do you need a suite if you only have one or two kids except for better chances for sex? (Once you get to three kids you do kind of need a suite if only because it gets hard to fit everybody into one regular hotel room.)

This gets into an interesting question, when is too old to have sex in front of your kid. You can clearly have sex when a kid is one, two, three or younger, I think. But somewhere around the age of three or above the kid might understand and remember seeing dad doggy style plowing mom and I think that could stunt his future development. (What if every serial killer saw his parents doggy styling at five years old? Like, we have all these trained psychologists trying to figure out what makes serial killers exist and it turns out it’s seeing dad reverse cowgirl mom when he was five?) 

Anyway, four years old is a tough age because it’s definitely possible he remembers mom and dad banging beside him in bed for the rest of his life. I don’t think you can risk that. Because then, at a minimum, he definitely grows up to like the freaky incest pornhub category.

And it will all be your fault.

I think the only play you have here is waiting for him to fall asleep and then having sex in the bathroom. Sure, he might wake up and come knock on the door, but what else can you do? You can’t bang outside the hotel room like 19 year olds on spring break. (Although I’ll be damned if any dad on a jury anywhere is convicting another dad for indecent exposure if you get on the witness stand and say, “We were just trying to avoid our son seeing us have sex and I didn’t think my wife would actually agree to it, but once she did what was I supposed to say?”)

So have fun in the bathroom. 

“So let’s just go ahead and state that this may be the most embarrassing mailbag from a girl, ever. I don’t even want to send it from e-mail, but anyways, here it is…I am a single 26 year old living in Nashville. About a year or so ago I met a guy in a bar in Midtown. We went on a date the next day, but I just wasn’t feeling it. However, I was feeling a friends with benefits type of thing (you know, to keep that number down).

So I had recently gone to the lady doctor and gotten a biopsy (which is hell FYI). Anyways, a few days go by and the weekend is here. I run into, lets call him Stan, at the bar and end up going home with him. We end up hooking up and afterwards I go to the bathroom to realize that I obviously had not healed from the biopsy… blood on my skin…the sheets and all. It was dark and he was drunk so he didn’t notice and passed out.

So once he was asleep, I snuck out at 3 AM. A few months later we run into each other again. I was super embarrassed but he kept insisting we go home together, so I thought maybe it wasn’t as bad as I thought…until we get home and he asks why I left and he had to wash the sheets the next day. Well it had been a while since I had been with someone, but we of course did the deed. Well once AGAIN I bled on the sheets due to lack of action (or should I say trying to keep some morals). First of all, HOW does this happen TWICE to someone?! Once again I let him go to sleep and booked it out of there…only to run into his roommate as I left.

I got texts the next day asking if I was okay and why did I leave. I have also gotten numerous late night drunk dials and texts asking why we don’t hook up anymore and if he wasn’t satisfying. Naturally the only option left was to block his number after these encounters. Yet somehow I still run into him all the time and he asks to hook up. I don’t know what my move is here. I am still mortified, yet if he’s into it should I keep it up? Is it super strange that he is not as freaked out as me? Should I run for my life? Stage 5 sex clinger or what?”  

Guys will forgive much worse flaws than bloody sheets if it leads to sex. 

He probably assumed you just happened to either be entering, on, or leaving your period both times you hooked up. I actually don’t think this story is that mortifying for you.

And if it makes you feel any better, he is probably texting 15 different girls when he texts you to see if you want to hook up again.

If you like him, third time’s the charm.  

“Hi Clay, first time mailbagger. My husband and I celebrated our 10 year anniversary this past spring. We splurged on our trip, and stayed at a very nice place somewhat out of our league (but it was our anniversary, so what the hell.) On our first day, while lounging by the pool, I began to notice a common scenario. There seemed to be an abnormal amount of couples consisting of extremely beautiful women paired with unattractive men. When I say unattractive men, I mean it.

Once I became aware of this scenario, I noticed it more and more during the course of the week. Now, I will say that personality can go a long way. None of these men seemed to have a lot going for them in the personality department. At least not that I could tell in my very brief observation. So, I came to the logical conclusion that these must be rich men. Really rich. I mean, several of them had children with them, so these beautiful women are sleeping with these not beautiful men. This leads me to my questions for you, oh wise one.

You don’t ever see this scenario reversed. Think about it, name one famous couple that consists of a really hot guy, with a not hot woman. So what is the equivalent of the hot woman/ugly man pairing, if the scenario is reversed? The only thing I can come up with is sometimes you see skinny dudes with “larger” women (sorry, that was so rude, I promise my pearls were clutched while I wrote that.) Is this an accurate scenario or can you come up with an equivalent for the hot woman/ugly man couple?

I think it would be extremely interesting to research exactly how much money it takes for women to decide that looks no longer matter. Is it $1 million or is it closer to $10 million? I think earning potential is important too, but that’s risky for the woman. I guess everyone has a different threshold, but I do think there is some sort of average out there that could be researched. What is your best guess to what that number is? And wouldn’t this be fascinating to chart – someone get Malcolm Gladwell on the phone.”

My theory: Start at a million dollars, with every million dollars a man has his average rating scale on a 1-10 basis increases by a point. So a guy who would be a five is a six if he’s a millionaire. 

Once a guy hits ten million dollars in net worth, his looks have zero impact on the women he can snag.

This is obviously on the east and west coast.

It takes even less money to snag a hot chick if you’re in a rural area. If you make $250k a year in most rural towns, you’re a ten.   

That’s because money and power attract women more than looks. This makes total sense when you think about it from a biological perspective. Every relationship is essentially about creating offspring. 

The more rich and/or powerful a man is the more likely his children are to survive. Women are biologically driven to pursue wealth and power while men are biologically driven to pursue young and attractive women. Why young women? Because they’re more fertile. Why attractive women? Because the more healthy a woman appears the more likely it is our offspring will survive. (The ancient cave man didn’t have DNA charts, he had his eyes. If a woman looks fertile and healthy, she probably was.) 

Pretty much everything we see in human mating behavior is directly connected to biology. It’s all about continuing the species. 

Want an easy analogy from modern day politics — think about the number of women who were — and even still are — willing to bang Bill Clinton, who has vast amounts of wealth and power, compared to the number of men who would be willing to bang Hillary Clinton, who is likely to be our next president.

The PC Bromanis out there would say this is a cultural construct, that society made men and women have these opinions and that the disparate treatment is an example of raging sexism.

That’s bullshit.

It’s biology, stupid. Women would sleep with Bill Clinton because he’s rich, powerful, still able to father children and their offspring would have a great chance to survive and thrive. Men would not sleep with Hillary Clinton because she can’t have children and so the sex isn’t attractive to them because it makes no biological sense.

Biology is so sexist!

I’m off to the SEC spring meetings.

As always, send your anonymous mailbag questions to

Anonymity assured.  

Written by Clay Travis

OutKick founder, host and author. He's presently banned from appearing on both CNN and ESPN because he’s too honest for both.