Anonymous Mailbag

Charlotte McKinney, Kliff Kingsbury

It’s Tuesday, time for the anonymous mailbag. 

As always these are all real emails sent from real Outkick readers. Send your questions to, total anonymity guaranteed. 

Here we go:

“So I was in the military years ago stationed in Texas. I had what we called a mod-mate in the barracks there (we shared a kitchen and bathroom but had adjoining bedrooms). I haven’t been there long and really don’t know the guy but he seems a little sketchy. One of those guys that if not for joining the military would have likely spent his early 20’s hanging around his high school selling skunk weed out of his Iroc. At any rate, one night there is commotion coming from the kitchen area outside my room, so I go to investigate and walk out to see this dude and three of his friends standing around in the kitchen naked drinking beer. I look into his room and a fourth naked dude is having sex with some girl. It dawns on me that I have walked into the middle of a train in progress.

This conversation ensues

“hey bro, you want to get in on that? We met her at the bar and brought her back, she’s totally down for it.”

“Nah man I’m good, I think i’m coming down with a cold.” (I understand that’s a weak excuse but I had never adequately prepared for this scenario)

A few weeks go by and I notice that my mod-mate now spends a lot of time on the phone talking to somebody, one weekend he gets all dressed up and is sitting around the living area and he says he’s waiting on his girlfriend. As you may have gathered by now, his new girlfriend was the very same girl that him and all of his friends brought home from a bar and queued up to gang bang. I moved on a few months later but to my knowledge they were still together.

I have never heard of a scenario like this before or since. How is this possible? How does the guy bring this girl around his friends who have all watched each other grunt on top of her? What do they say when people ask how they met? Will he one day remove his spectacles with a twinkle in his eye and hold her hand while telling their grandchildren that he was the third guy in the train but he could tell they really had a connection?”

Do they talk about the gang bang experience later? She has to lie to him and tell him he was by far the best of the four guys she slept with that night, right?

We need Todd Fuhrman to set odds for a relationship that begins in a gangbang.

Here are my rough odds (a negative number means it is very likely to happen):

Divorce: -8000

Illegitimate child: -10000

Child or parent goes to jail: -7000

Married for fifty years and lives happily ever after: 100,000 to 1


Last week, I got that email that every law graduate has nightmares about. Yep, you guessed it, the dreaded “We regret to inform you that you failed the (insert state) Bar Exam.” And while I wouldn’t compare it to getting positive AIDS results, it was still a pretty devastating experience.

You’ve written on this topic before. Not to beat a dead, gay, muslim horse but I’m going to need your sage, not so legal career advice.

Ever since college I wanted to go to law school because I thought it was the best way to being important (I know, I’d punch my 20 year-old self too). When I got to law school, it was the rudest of awakenings. Why did I continue for three years? Masochism I guess.

While I genuinely enjoyed writing and public speaking and got pretty good at it, I hated every academic aspect of law school. The thought of studying for another bar exam is making me want go all self-immolation, Tibetan Monk style.

After the entire experience, I’ve come to believe that nothing stifles intellectually curious thinking more than law school and the legal profession. Keeping in mind that I went to a very average law school and got very average grades and am very white and very male, what do you think of JD’s doing something completely different than law out of law school? Is it feasible? Do we have options?”

Studying for the bar exam is one of the worst experiences in academic life. Because you spend three years — and tons of money — on law school, but once you graduate all you have is the right to take the bar exam. You don’t actually have anything tangible, just an entire summer of hellish bar study. 

I took bar exams in back-to-back summers — because I’m a glutton for punishment. The first year exam — the one in the Virgin Islands — was the most stressful for two reasons 1. There was no course. I just bought a multistate book and then studied essay questions all by myself for a couple of months and 2. you start practicing without knowing your results for several months. It’s great to find out you pass, but mostly you just dread finding out that you failed because everyone in the entire firm, all your friends and family, everyone knows about your pending exam. And they publish the results so anyone can go look them up. Plus, then the stress level is infinitely higher the second time you take it and have to pass or lose your job. 

The second time I took the bar exam, though, was the toughest because at least I was home with nothing else to do but study for the first bar exam. The second time I took the bar exam while I was practicing full time. So you finish your work and then go home and study the entire damn thing all over again. (Yes, I had to retake the multistate which is hellish. That makes zero sense, it’s like having to take the SAT every time you apply to a different state bar exam. It’s the same test nationwide!)

Anyway, presuming that you have some financial flexibility, I’m here to tell you that most lawyers don’t really like being lawyers. So if you can find something else that you think you’d like to do, I’d pursue that job while studying for the bar exam. I think you need to take it again — after all, you want to actually be licensed after spending three years in law school, but I’d use this as an opportunity to find something that you really think you’d love to do instead of practicing law.

Good luck. 

“My story involves my now wife-then girlfriend meeting my parents for the first time. My parents lived about two hours away from where my girlfriend and I were living at the time, (southern state, not Deep South though). So we decided to get an early dinner, no big deal. I had a burger and she got a salad and a beer.

We go to my parents house and everything is great. She likes them, they like her. At bed time, she mentions her stomach kinda hurts. She takes some Mylanta and we go to our room, two beds one room. My girlfriend wakes up sick and throws up in the bathroom. While bad, that’s not the end of the story… While she was throwing up, there is no easy way to say this, she pooped herself. So, throwing up and pants pooping, is bad right? Not the end of it. While continuing to use the bathroom she ended up clogging the toilet, to the point where my dad had to take the toilet off the floor to get the clog.

Did I mention that we only had one bathroom, no? Yeah, one bathroom and toilet. You might ask, “where were you?”, I slept – the entire time. My mom and dad stayed up all night with her. She got to know my parents after she shit herself and broke the only toilet in the house.

I put a ring on it shortly thereafter.”

Once she clogged the toilet, how could you not put a ring on it?

Incidentally, this is every woman’s worst nightmare with a first ever in-law meeting. Actually the worst thing that could ever happen.

I’m not even kidding about this.   


Long story short:

– 20ish friends go on a trip to (foreign country).
– Buddy bangs girl.
– The following day, same buddy proposes to different girl.
– She says yes, clearly not knowing what transpired the night before.
– Everyone knows of the happening, except her. (Talk about embarrassing, right?)
– He’s been known to cheat on every girlfriend he’s ever had.
– None of us really like his fiancee. But she doesn’t deserve this. (In her defense she’s really nice, she’s just incredibly boring. Sort of a fun sponge.)
– A few of us have already called him out – “Intervention” style. (Accomplished nothing)
– Now he’s asked us to be groomsmen.
– My wife (and all the other females on that trip) are considering a full-fledged boycott of the wedding. But I feel bad abandoning the ship on a bro like that.

Moral of the story – he’s a great guy friend who is simultaneously a shit significant other.

What’s the play?”

One of your wives tells the fiancee. If someone doesn’t volunteer to do this, all the girls draw straws. Before drawing straws all the girls agree that they will support whichever girl has to break the news so your guy friend can’t hold a grudge against the girl who breaks the news to his fiancee.   

This way the fiancee’s fully informed and can choose whether to go through with the wedding. It’s unfair for everyone to know this information except for her.  

You guys have already done the decent thing and tried to get him to call off the wedding after an intervention. But he’s your friend so I understand not wanting to jeopardize your friendship over telling on him with his fiancee. Plus, once you’ve made it clear you don’t agree with a wedding decision, what more can you do without risking the friendship? Sure, if you’re forceful he might listen to you. But what if he marries her anyway? 

By the way, am I the only person who wants to hear from the girl he slept with the night before he proposed to another girl? Was she present for the proposal? What the hell was she thinking? Sure, the girl he slept with here isn’t blameless, but she probably was thinking that, you know, the relationship was on the outs as opposed to about to be united in holy matrimony. 

And while we don’t get into being moral police in the mailbag, can we just take a moment to consider that this guy traveled to a foreign country with an engagement ring for his fiancee and SLEPT WITH A DIFFERENT GIRL ON THE SAME TRIP THE NIGHT BEFORE HE PROPOSED. 

It’s a cliche, but men really are idiots when it comes to sex. 

“My wife and I are mid 30’s have a few kids and a normal married sex life. Recently my wife has started sending me naked pictures of herself. At first thought, any man’s reaction should be Great, this is awesome. It is great, but also kind of strange. It’s hard not to laugh honestly when I get them. Am I weird not to be thrilled with this? its just the thought of her at home by herself taking these pictures makes me laugh. I do appreciate the effort though.”

You’re married with kids and your wife is sending you naked photos during the day and you aren’t thrilled?

Yes, you are weird. 

“Back in the spring, following the Mayweather-Pacquiao fight, I tried to get an Uber on Saturday night in downtown Nashville. 

After about 15 minutes, I got frustrated because so many people were around and my Uber driver either couldn’t find me or someone had hijacked my ride. I decided my best bet was to walk away from the crowd and get to an area that would be easier for them to pick me up. About the time I got even with Flying Saucer, my phone rang and my Uber driver said he was pulling up to Bridgestone. I told him that I had began walking and he could pick me up in front Flying Saucer. About 2 minutes later, a car pulls up next to me with a well-dressed heavy-set man in his 60s and asked me where I was headed. Assuming this was my Uber driver, I hopped in and away we went.

A few minutes into the ride, I notice that he doesn’t have his phone or GPS out running the Uber app like most drivers do, so I became suspicious. I asked, “So how do you like driving for Uber?” To which he responds, “Oh, I dont work for Uber. You just looked like a decent guy that needed a ride, so I thought I would pick you up.” Inside my head all I can think about is they are going to find me in the Cumberland River tomorrow because I just got kidnapped, but I remained calm and tried carrying on a normal conversation. All the while, I had my right hand on the door handle and my left fist clenched ready to punch and roll if he made any false moves or wrong turns. As we approached my street, I decided to tell him I lived in the apartment complex across the street and he could just pull into the bank parking lot because there was no way I wanted this guy knowing where I actually lived. He pulls into the bank parking lot, but keeps driving and pulls behind the bank where it isn’t as well lit.

I immediately fling the door open and hop out as soon as he comes close to stopping. As I am closing the door, he says “Wait!” and is reaching for something in his pocket. My first thought is “Oh shit, it’s a gun”, but before I can react, he throws a $20 bill at me. I toss it back to him and say “No thanks, I appreciate the ride and dont need your money man.” He throws the money back down on the seat and says, “But don’t you owe me a favor?” I replied, “I don’t owe you shit weirdo,” slam the door and take off running through backyards to make my way down the street to my house. As I am running away, I can hear him yelling at me calling me a “turkey,” who does that these days?

My only regret, other than risking my life and/or being sodomized, is that I didn’t tell him it was gonna cost more than that and snatching his money before I ran. Please keep me anonymous as I don’t want this pervert who thinks I owe him a “favor” knowing who I am.”

First, I love your assumption that the pervert’s an anonymous mailbag reader. We’re huge with the over sixty fake Uber driver community. 

Second, does this guy make a habit of driving around downtown Nashville, picking up drunk single guys, driving them home and then trying to pay them for sex acts? Doesn’t this seem like a really low percentage play?

Third, I would have loved if you’d paused as you were sprinting away and yelled back, “And if you think I’m going to jerk you off for $20, you’ve got another thing coming, turkey.”

We got a ton of fake Uber driver pick up stories from you guys, by the way. Be careful out there. 

Send your anonymous mailbag questions to

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.


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