Anonymous Mailbag

Charlotte McKinney, Kliff Kingsbury

It’s Tuesday, time for the anonymous mailbag.

As always, send your anonymous mailbag questions to, anonymity guaranteed.

(Make sure you read all the way to the end for the final question and answer).

The anonymous mailbag is brought to you by my friends at 30A cottages, why stay in a tiny hotel room or a condo when you can stay in a mansion on the beach? Go check out their offerings here.

On to the mailbag:

“My teammates and I are big fans of yours and you’re about the only reason I keep checking Twitter! It’s refreshing that there are still people out there who aren’t afraid to speak their minds in this PC culture we live in today.

I have always wanted to submit something to the mailbag and I finally have something:

My girlfriend and I have been dating for several months now. This is not a relatively long time, but it is enough to know that this girl is an absolute catch and that she is wife material. She has also expressed to me that she would want to marry me down the road. For the past two months, we have been doing the long distance relationship deal which is new for both of us. I play football at a SEC school and she is in a sorority at a Big 12 school.

Her sorority does a formal later in the year that I will not be able to attend since my team will have our spring game on that day. She was telling me that it was socially acceptable to ask a different guy to this formal if your boyfriend is not able to attend. Now I am obviously not a fan of this idea. I have lightly expressed my dislike of this idea to her, but she insists that there is nothing to worry about. She has done nothing so far to make me not trust her. She has a flirtatious personality and I know how college guys work (especially when alcohol is involved). I don’t want to make this a big deal and come off as a controlling dick to have her make me the bad guy in this situation. At the same time, I don’t want to be passive and not say anything to let this slide (#dbap).

How do I talk her out of taking another guy without coming off as the bad guy? Is it naive of me to just trust her with another guy? What’s my play here?”

First of all, if you play football at an SEC school and you have a girlfriend at another school the only thing I can think is that this girl must be the smokeshow of all smokeshows. 

But I’d still advise you, like I advise all college guys, not to have a serious girlfriend in college because when you’re 36 years old and married you’re going to be thinking back on all the girls in college you wish you’d hooked up with, but didn’t. But that’s for you to discover in the future. I’m just the old dude here guaranteeing that at some point in time you will be where all married guys are, thinking back on the girls you wish you’d hooked up with when you were single. 

Selfishly I want a top SEC athlete to make the decision that he wants to have as much crazy sex on campus as possible and then write a tell all book about the experience. Like, for instance, what if Matthew Stafford was a total poonhound, was funny, and wrote an incredible tell all book about all the sex he had while quarterback at Georgia. Tell me you wouldn’t drop everything to read that book. How about the time Jamal Lewis had sex with nine different girls at the same time? (I just made up this story, but I’m convinced it happened). That’s the SEC Storied I want to watch or read. 

By the way, I’ve totally pitched Matt Leinart on writing this book. His stories are incredible. Can you imagine being a good looking dude at the helm of the USC dynasty in LA when they had no NFL team and then getting drafted top ten and moving to freaking Scottsdale, Arizona? You can make a strong argument that Leinart was surrounded by more hot ass than any quarterback in football history.

Okay, back to your question: if your girlfriend is really hot and she takes a guy to her sorority formal there is a 100% chance that the guy will be wanting to hook up with her. You know this, I know this, every guy reading this knows this. Moreover that guy’s already thinking about hooking up with her even when he’s playing the, “Of course, we’re just friends!” angle. Now chances are the kind of guy who goes to a sorority formal with a girl he’s friends with when that girl has a boyfriend is kind of a pussy, but toss in alcohol, your girlfriend being dressed up hotter than normal and the usual sorority formal shenanigans and it’s totally feasible that she could hook up with this dude.

I’m not saying she will do it, but I’m saying it’s perfectly normal for you to think she might and the guy she is going with will definitely hook up with her if he gets the chance. So this is entirely her call.    

Now hot girls are different than dudes because guys are always trying to hook up with them all day long every day. The only male comparison has to be what it’s like to be a starting quarterback at a football school or what Ryan Gosling’s life is like in Hollywood today. There are like .001% of dudes who have any clue what this feeling would be like, for women trying to be banging you everywhere you go. So whereas virtually all men have to work pretty hard for sex, hot girls live with an ever present reality — they can pretty much have sex whenever they want with whomever they want.

So here’s what I would request — does your girlfriend have a gay friend she could go to the formal with? This is the perfect occasion for you to champion a gay friend date. Then he gets to dress up and party and you have no worries whatsoever that she’s going to get drunk and hook up with him. As an added bonus you seem really gallant and progressive for making the suggestion.

If she doesn’t have a gay friend, why can’t you bring her to town for the spring game? Wouldn’t most girls rather watch their boyfriends play in an SEC spring game than go to a sorority formal?

If she doesn’t have a gay friend and she doesn’t want to come to the spring game, I don’t think you have many options left. You have to be cool with her going to her formal without you and trust her not to hook up with the dude she’s going with. Yes, the dude you know is definitely hoping the girl will hook up with him.

I just don’t think you can forbid her from taking a date if everyone else has a date. 

I know it seems like a really tough spot right now because you’re in college and you think this girl is the one for you, but trust me on this — you really don’t have much to lose here. If she hooks up with him then you break up with her and are a single football player on an SEC campus. If she doesn’t hook up with him, then you have even more evidence that she might be the right girl for you.  

Good luck. 

“I am a 50 year old lawyer and father of two. My youngest is a high school sophomore. I am pretty liberal on social issues and believe pot should be legal. I also recognize high school kids will drink and smoke pot, though they probably shouldn’t. 

This week my 15 year old told us that some 14 to 16 year old friends are regularly taking Adderall, Xanax and smoking pot at school, drinking hard liquor to the point of blacking out on the weekends, and driving while high. Most 16 years can’t drive well at all, let alone with a little weed in their system. Indeed, the school apparently received an anonymous tip (not from me) and have now suspended 10-15 freshman and sophomores for possession at school.

However, my 15 year old advised that one girl who was not caught is “one of the worst.” Upon being cross examined, my 15 year old bases the information on social media observations and from what other kids have said. No first hand knowledge. 

Notwithstanding the unreliability of the information, should I reach out to the father of the daughter and pass along what I have heard? I have known the dad for 10 years but not very well. We say hi to each other when we see each other a few times a year, and talked for an hour over beers this past summer at an outdoor concert. 

I am torn between being a snitch, and being a parent who would want to know if my kid was engaging in potentially dangerous behavior. And, candidly, I don’t know anything about the safety of taking unprescribed Adderall and Xanax. 

Since you are a young, gay, hard partying Muslim, I am looking for “you’re” advice as to what I should do?” 

I don’t think your info is reliable enough to share with the dad, honestly. You probably remember how easy it was for rumors to spread about kids at school, even if those rumors were not based on factual information. That could be what’s happening here too. I think you need concrete knowledge to talk to him about an allegation like this and your daughter doesn’t have that concrete knowledge. 

If 10-15 kids just got suspended at school, I do think you can talk to the dad the next time you see him and discuss the drug issue in general, potentially even mentioning your own kids and fears or concerns surrounding them. If that many kids got suspended it’s something that I would imagine all parents are discussing. And, honestly, if I heard that happened at one of my kid’s schools I would certainly sit down with them, even if they weren’t suspended, and discuss this issue with them.

So I’d have a generalized discussion with the dad. Because chances are he’s already talking with his daughter about the suspensions. But I’d stop there.  

“I played D1 baseball and was recently the best man in one of my teammates weddings. Most of the wedding party were also former teammates of ours and all of us are 23-27. His now wife is very religious and not a fan of some of our ‘single lifestyles’. He is by no means a great looking guy and has definitely outkicked his coverage.

Anyways we get a beach house for the bachelor party on a pretty nice beach also where there is a pretty decent night life. She makes me promise her that I won’t take him to a strip club, obviously I tell her what she wants to hear knowing that we’re definitely going to one. The first night there was great but we end up getting too drunk and forgetting all about going to the strip club.

So the next night we go to a few bars and as we’re walking to find another one, we come across a strip club. We stand outside that place for at least 45 minutes trying to convince him to go in but he is so scared of his wife finding out he refuses. He ends up passing out on the way back to the beach house and gets 45 MISSED CALLS from his soon to be wife. We get back and he calls her back and apparently they share their locations with each other and she is pissed that he didn’t tell her we were going to a bar.

In trying to defend himself he tells her we tried to get him to go to a strip club but he refused. That ends up pissing her off even more and now she is also mad at me. Well the wedding goes on and they now have been married almost 2 months. So this is where my problem comes into play. One of our teammates who was also a groomsmen at his wedding and present at the bachelor party just got engaged. Much of the same group are going to be groomsmen in his wedding including myself and the newlywed. We have all just started talking about bachelor party ideas for this wedding but Mr. Newlywed has already said he won’t be attending because his wife won’t let him because she doesn’t trust myself and a few others in the wedding party. So my question is how much of that is bullshit and she is just insecure as fuck? And also how do I get him to come to the bachelor party? Because this might be the only time I ever get to hangout with him again.” 

Your buddy is either going to get divorced or be miserable for the rest of his life. 

I see no other options for him. 

Because your buddy’s wife may well be psycho.

First of all, 45 MISSED CALLS!


If anyone ever calls you 45 straight times you need to break up with that person immediately. I don’t care what the reason is, that’s indefensible. What made her think that after 20 the calls were going to work? 

Second, they share phone locations with each other and she was tracking his movements on his bachelor party? Holy fuck, she’s psycho. Am I the only person who doesn’t share his physical location with people on his phone? The only way I can see this making sense is if you’re a parent and your kids are underage and you want to keep tabs on them when they’re out at night. The idea that two grown people would do it is terrifying to me. 

Third, and I keep having to say this, if you’re worried about your fiance hooking up with someone at his bachelor party, it’s much easier to hook up with regular girls than it is strippers. If you’ve got a bunch of guys out at a bar, chances are they’re going to meet girls and those girls are more likely to end up sleeping with your fiance than the strippers are. Women who are terrified of strippers have likely never been in a strip club. That’s a commodity based business, the strippers aren’t looking for hook up partners, they’re looking to get paid.

Unless you’re paying for sex — which is a whole different ball game — then strip clubs are where you should want your fiance and his friends to be spending time. 

If you’re worried about your fiance seeing boobs, wouldn’t you rather him see pro boobs rather than amateur boobs? 

“Well damnit Clay I did it. I wasnt happy and called off the wedding 6 months before it was supposed to go down. Things weren’t good, neither happy, but no cheating. She hasnt given the ring back yet, but we have talked about it so I know she knows it’s the right thing to do. 

But that leads me to my question – How soon is too soon to get back out there and chase beautiful women here in Austin where I live? 6 months? 3? Can I bang a random at the bar this weekend as long as I pour a beer out first in honor of my ex? Do I bang a cougar or a 23 year old chick fresh from UT first? Maybe a hippie with piercings in all the right places?” 

Once you call off the wedding I think you’re totally within your rights to start chasing girls immediately. 

Having said that, I’d be discreet about it. I wouldn’t go on social media and post pictures doing body shots off girls in the Austin bars. (Incidentally, this happened to a buddy of mine. The girl he was madly in love with broke up with him after multiple years of dating and the next thing she posted on Facebook was dudes doing body shots off her on a yacht during spring break.) You also have to assume that your ex-fiancee’s friends are going to be watching you and reporting back.  

The big question here is how much do you want the ring back? Because the more aggressive you are in broadcasting your availability on the open market the more likely it is that she keeps the ring out of spite. 

As for who you should hook up with first, I have no idea how anyone’s first choice isn’t a recent college grad. If you can hook up with a 22 year old college girl, you hook up with a 22 year old college girl.

You’ll be able to bang cougars and hippies for the rest of your life.   

“I’m in desperate need of some gay Muslim wisdom regarding the penis of my unborn son. I currently have two daughters (ages 7 and 3), and we just found out that we’re expecting our third who will be a boy. The topic (and surrounding debate) of circumcision has arisen, and so I would surely benefit from some guidance. Bottom line is that I’m circumcised, and just always assumed that any son I sired would be the same. My wife doesn’t necessarily disagree, but feels like it should be a discussion and a decision instead of an automatic assumption. For what it’s worth, she grew up with no brothers and has allegedly dated very few adult men.

My guy friends are useless. Actually, they’re more than useless. When I even brought this topic up, it turned very weird, like this was almost taboo to discuss. Somehow we can raucously debate even inch of female anatomy, but everyone gets strange when we talk about our own foreskin or lack thereof? Without addressing which is better, they all say that the son should be like the dad.

I understand that most white American males are circumcised, but I know there’s plenty of exceptions to this. I’ve spent plenty of time in lacrosse locker rooms (Syracuse ’01!!) and seen my fair share of penises, so I have a pretty good idea of the breakdown. Religion doesn’t really factor into this for myself or my wife, but she’s being extremely stubborn. She insists that while the bulk of women prefer circumcised men, we’re not giving the decision its fair weight by just going with what everyone seems to be used to.

So my question to you is this… does the almighty Imam have any strong opinions on the specifics (cut versus uncut)? Do you feel like there’s benefit to Sonny looking like Daddy, or should Sonny’s schlong get considered on its own merits? Do you think that the average male will be facing any real locker-room or dating discrimination 18 years from now?”

I’ve got three boys and I’m circumcised so I think it makes total sense to also circumcise them so they look like dad. 

If your wife wants a medical benefit, circumcision appears to substantially decrease the rate of HIV for heterosexual men. By a whopping 60 percent. It also decreases the odds of herpes by 30 percent. That seems pretty valuable. I’d also just give her this wikipedia page and tell to read it about herself.

91% of white men are circumcised — including 77% overall in the country. You are white and circumcised, doing the same thing for your son is the smart decision. 

“My husband introduced me to you and your website a few months ago. I’m a fan. I appreciate your blunt but honest reflection and commentary on sports and the news. I listen to your shows and read outkick.

This leads me to my question. How many female fans do you think have sex dreams about you? I had a very graphic sex dream about you last night. I woke up blushing. Have you considered this side of fame and notoriety?

For the record you didn’t finish (sorry) but it was still a crazy way to wake up…with an odd sense of guilt. I imagine other readers have had this experience?! I feel like a dirty slut.”

Happy Valentine’s Day!

I don’t think that many women have sex dreams about me — including my own wife — but if it adds some spice to your life, I’m happy to offer my pulse pounding good looks to your dreams (or nightmares).

This, by the way, would be incredible to see, I’d love to know everyone’s all time masturbation meter. That is, not the number of times you’ve jerked off yourself, but what if everyone on earth knew the number of times guys or girls had masturbated while thinking about them? It was like your batting average. Obviously women’s numbers would skew way higher than men’s, but this leads to another fascinating question: who do you think is the most masturbated to man and woman in the history of the world? I mean world wide, not just in America.

Couple of important parameters that I think will help you come to an opinion: First, given the world population there’s no doubt that person is alive today. That is, there are more people jerking off now every day than would have jerked off in all of like 1504. (And who do you think people jerked off the most to in 1504? Had to be the hottest chick in every village and her numbers would have been tiny.) Second, it’s not going to be the hottest person it’s going to be the hottest person that the largest number of people know.

With that in mind, I’m going with Madonna for the most jerked off to woman in world history because she’s been high on the jerk off rankings for like forty years now.

Beyonce, Shakira, Britney Spears, JLo, they’ve all posted big numbers in the past 20 years, but they don’t have the jerk off longetivity of Madonna. 

As for men, this is tougher, but I think it’s Tom Cruise. He’s been a movie star for thirty years now and everyone in the world, pretty much, would know him. So I think it has to be an actor and I picked Tom Cruise over Brad Pitt, Denzel Washington, Will Smith, Leonardo Dicaprio, George Clooney, the Rock, and Johnny Depp. I think these eight dudes would probably be the most masturbated to actors of all time. 

I had Dicaprio in second place on my list because you know that starring as Jack in Titanic had to send his masturbatory rankings just absolutely soaring. I’m not sure there has ever been a more masturbated to male character in the history of pop culture than Jack from Titanic. But Tom Cruise did “Top Gun,” like 12 years before Titanic ever happened. So I think Cruise has more masturbatory longetivity banked.   

I was tempted to go with a former president just for total fame’s sake, but do you really think that many women in Iceland are burning up the sheets thinking about Bill Clinton, George W. Bush or Barack Obama?

The only other possibility for men was rock stars and I think a guy like Mick Jagger or Paul McCartney would have huge numbers too, but I don’t know that a random woman in Thailand is furiously masturbating over Paul McCartney. Other famous musicians like Justin Timberlake just aren’t old enough to have racked up huge numbers. Michael Jackson is intriguing, but he got so weird I don’t think most women found him sexually attractive.

And Elvis died too young.  

So I’m going Tom Cruise.  

Further fun question, do you think I rank tops in sex dreams for the sportswriter category or do you think there are secretly a ton of women out there having sex dreams about Skip Bayless, Rick Reilly, Tony Kornheiser and Michael Wilbon? Because all those guys are more famous than me.

But if you have a Skip Bayless sex dream do you tell anyone at all? Can you even look at yourself in the mirror in the morning?

Honestly, we need an entire anonymous mailbag that’s just filled with secret, embarrassing sex dream confessions. 

I remember one of my buddies in 8th grade made the mistake of telling us that he’d had a sex dream about our French teacher, Fifi Fenton. And we didn’t stop talking about it for years. In fact, there is a 100% chance that I’m bringing up this sex dream he had about our french teacher in 8th grade at our twenty year high school reunion this fall. 

Anyway, send your sex dream confessions to

As always, full anonymity guaranteed. 

And thanks for reading the anonymous mailbag. 

My teammates and I are big fans of yours and you’re about the only reason I keep checking Twitter! It’s refreshing that there are still people out there who aren’t afraid to speak their minds in this PC culture we live in today.
I have always wanted to submit something to the mailbag and I finally have something:
My teammates and I are big fans of yours and you’re about the only reason I keep checking Twitter! It’s refreshing that there are still people out there who aren’t afraid to speak their minds in this PC culture we live in today.
I have always wanted to submit something to the mailbag and I finally have something:

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.