Anonymous Mailbag

Charlotte McKinney, Kliff Kingsbury

It’s Tuesday, time for the anonymous mailbag. 

As always, you can email your anonymous questions to me at, anonymity assured

On to the mailbag. 

“During my college years I worked at a Christian summer camp. One year at the end of the summer we had a staff party and I decided to try the rope swing at the lake. Now I should say that the only reason I decided to overcome my crippling fear of heights was to impress a girl. She was a sorority girl from an SEC school, super hot, and completely out of my league.

When I went to attempt the rope swing I let go way too early and plummeted 15 feet to the bank below me. I landed on my knees and did a few somersaults before getting caught on a large root and my swimming trunks coming straight off. I landed right there with my head in the water on my back and my bare ass and legs stuck straight up in the air. Worse, the girl in question was standing about 10 feet away in full view of my dick, balls, and taint.

And let me be frank, it was not the most impressive sight.

Fast forward to last week. I proposed to that girl and we’re getting married next year. Is this the greatest comeback story ever?”

Dying laughing.

This is the Tennessee comeback against Florida transferred to Christian summer camp. (By the way, hate to rub in the loss to Gator fans, but that 38 consecutive points that Florida gave up to Tennessee was the most consecutive points the Gators have allowed since 1982.)


“I’m in my late-30s, married with one kid, and the wife and I are trying for number two. We’ve been at it for nearly nine-plus months now and have gone from timed intercourse, to oral medications meant to alter hormone production (with timed intercourse), and now just this month we’ve moved onto the next phase – my wife injecting hormones directly into her stomach and, you guessed it, timed intercourse. This is all very stressful for her, with doctors appointments seemingly every-other-day, and the cost of the appointments and shots really starting to add up. Add to all of it that these medications really mess with her internal chemistry, making her feel physically sluggish and a little emotionally unmoored, and you can see how it is a delicate situation. I’m loving the sex part, but it is starting to feel a little forced.

Here’s where you come in. We are in the first round of shots, she is being monitored, and the doctors are telling her that the hormones aren’t working as quickly as normal. So while they thought our 2-day window for intercourse was going to be in the beginning of next week, it now looks like it is going to be this coming Friday and Saturday. Here’s the problem, I am supposed to fly out first thing Thursday morning for an annual guys football weekend.

This is my once a year thing with friends who are scattered all over the country and whom I rarely get to see, which she knows is a holy endeavor not to be messed with. We’ve started talking about what happens if she goes in on Monday and the doctor tells her, “Nope, the window’s not gonna open until Friday.” She’s vacillated between telling me I have to go/don’t worry about it and saying I’m going to have to cancel the trip.

Some factors to consider: (1) Between flights and tickets, I have either spent or committed $1,200 on the trip, (2) Between the shots and doctors appointments, we’ve already spent $800 on this round of fertility stuff, (3) These amounts of money are not chump change to us, but they’re also not completely draining our rainy day fund or anything, (4) My wife is in her mid-30’s, so the biological clock is ever-present,.

So what do you do? Go on the trip and force your wife to go through the whole process again next month? Bail on your friends and stay back to have mandated sexy time with your wife, which may not even result in conception? I’m leaning towards cancelling the trip, but I’m wondering if there is another lens through which to view this conundrum. Thanks.”

You have to cancel the trip, unless, and this might be a risky move, you just bring your wife on the guy’s trip with you and sleep with her during breaks between football games.

Talk about having your cake and eating it too.

If bringing her too isn’t possible then you have to cancel the trip and I suspect you knew this before you even sent the email.


Don’t be a total asshole here. 

“I have a friend who loves to get obliterated every time he drinks. On a recent beach trip, we got into an argument (I cant remember what about) and he proceeds to leave the room in a drunken rage. He comes back an hour later from God knows where and bangs on the door, screaming explicit language and death threats if I don’t let him in. Only one problem, he was so drunk he is banging on the wrong door. Turns out the room was occupied by an old couple, and the husband, a war veteran, had PTSD. The banging on the door put him in a panic attack and he was rushed to the hospital the next morning. My drunken, idiot friend decides to write a letter of apology (the worst letter I’ve ever seen) and signs the letter off with “Until next time, his name.”

I ask him why on earth he signs off with this, and his reasoning was because he forgot how to spell “sincerely”. Is this the worst decision ever made? What was the right play for him here?”

I need to see this letter and we need to post it on Outkick.

I’d like to say I’m surprised that the kind of guy who would show up at the wrong door and drunkenly bang on it late at night while screaming curse words, sending a war veteran to the hospital with a panic attack, would not be able to spell sincerely, but this makes total sense to me.

I’d love to hear from the old man and his wife when they read this letter.

“Until next time, Maude, do you see this!”


“Need your help settling a tailgate dilemma. I’m mid 30’s, white and love a good tailgate. But part of the pre-game fun is listening to music at high volumes. Unfortunately because I refuse to download censored versions of songs it puts us in awkward situations from time to time. This happens when a rap song comes on and the N word happens to play as a group of black fans walk past us. As you can imagine the reactions are not always great.

I assume I’m in the right as I’m not the one singing the song and I should have every right to listen to whatever music I enjoy. Do you agree that PC Bros shouldn’t be able to censor what music white people listen to? Side note, I’m also a Mizzou fan and feel compelled to turn the tide on the PC bullshit as of late. #dbap”

It isn’t your responsibility to censor songs. If an artist is okay making tens of millions of dollars off his or her lyrics, then you should be able to play those songs at your tailgate. (Although we’re not far from hearing from the PC Bromani community that white people liking rap music is cultural appropriation and hence not allowed. Just wait, this is coming).

I happen to believe that our societal obsession with saying certain words are “bad” is so mind numbingly dumb that it nearly drives me insane. Words mean nothing without context. If, for instance, you’re playing Kanye’s “Gold Digger” and these lyrics come on:

“Now I ain’t saying she a gold digger
But she ain’t messing with no broke niggas
Now I ain’t saying she a gold digger
But she ain’t messing wit no broke niggas
Get down girl go head get down”

That’s totally different than Riley Cooper screaming a racial slur at a dude at a Kenny Chesney concert.

Context matters, but our society is so dumb that instead of using our brains we make artificial prohibitions that just make everything worse.

This is like the mailbag question we got a while back from a guy asking what he’s supposed to do when he performs karaoke and there’s a racial slur in the song. Well, is it a racial slur in the song or not? Just about all the time in rap songs, it isn’t.

So if Biggie’s “Hypnotize” comes on at karaoke are you really telling me that karaoke, WHICH EXISTS SO YOU CAN TRY AND SOUND AS MUCH LIKE THE ARTIST AS POSSIBLE THAT’S THE ENTIRE PURPOSE, that you’re supposed to skip words or just hum them so people don’t think you’re racist?

This is just so absurd.

I think the bigger issue with your tailgate songs is this — just make sure the people at your tailgate are adults. I’d be more troubled by you blaring out songs with expletives in them when parents are walking by with their kids than I would be rap lyrics dealing with race.

Also, for the record, I don’t worry about being called racist or sexist, I just treat everyone like an asshole.


That’s the most equal I can be.

“I have myself in a big bind. I have been married two years, and I’m happily married. We are both 26, and we have no kids.

So, my best friend is getting married in August of 2017. I am the best man. He is dead set on going to Vegas for his bachelor party. But my wife is 100% not letting me go. I have never cheated, so she has no reason to not let me go. We both have good jobs. We easily have over $75k in savings so money isn’t a reason why I shouldn’t go.

What’s my move? How can I convince the wife to let me go. Being the best man, I have to go, and he went to mine in NOLA. I need a smart play by a smart guy like you.”

First, you’re an adult, your wife can’t keep you from going somewhere. What’s she going to do, divorce you if you go to a bachelor party in Vegas? If she’s willing to do that then go ahead and get divorced now and save yourself the awful marital years ahead.

You’re 26, you have no kids, and there are no financial concerns here — I’d just tell her I was going whether she likes it or not.

Tell her you’d never stop her from going on a bachelorette party with her girlfriends and you think it’s absurd that she’s trying to keep you from going on a trip with your guy friends.

It’s important for you to send the message now that she doesn’t get to make decisions for you like this. Granted, one day she will make virtually every decision in your household, but that will be once you have kids and your life is over. You aren’t there yet.

So sit down with her and have a rational discussion with her about why she doesn’t want you to go to Vegas. Ask her what her fears are about this trip.

My guess is she doesn’t trust your friend(s). All guys have friends that the wives or girlfriends hate because they believe these guys are bad influences on the other guys. Once this comes out then say it disappoints you that she thinks you aren’t capable of making your own decisions. Allay her concerns by promising her that when your buddy is balls deep in a stripper in the VIP, you will be downstairs drinking in the strip club by yourself.

Tell her you’re going to Vegas and when you get back the two of you can take a trip together.

“I’m 24 and single and my friend is 24 and got married in July. My buddy wants to hit up the bars downtown (on SEC campus) Friday night before the game and relive the glory days. I realize being 24 isn’t a huge deal to be going to college bars on a return trip to campus, but at what age does it become a little strange? And what effect does one’s marital status and gender have in this situation? I would think most college girls wouldn’t appreciate being hit on by noticeably older men, while every guy I know would brag endlessly about bringing home an attractive MILF (hot girl privilege strikes again).”

You guys are 24, you still have several years of being able to go to college bars and relive your glory days.

That’s like 90% of why people come back to campus for football games, so they can pretend they aren’t as old as they actually are.

The fact that you’re even worried about this right now is proof that you’re trying to grow up way too fast. I bet you’re maximizing your 401k too, aren’t you?

Want an easy test to know when you’re too old to chase college-aged girls? When they won’t sleep with you.

If Brad Pitt went to Gallette’s in Tuscaloosa tomorrow he could bang 99% of the girls in there and he’s 52.

Age is just a number.

Don’t believe me? Ask Joey Freshwater.

Send your anonymous mailbag questions to

We’ll have a live Outkick Show at 4 eastern today. 

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.