Anonymous Mailbag

Videos by OutKick

Charlotte McKinney, Kliff Kingsbury

It’s Tuesday, time for the anonymous mailbag. 

As always, you can email the anonymous mailbag at, full anonymity assured. 

Couple of notes before we get going:

1. Outkick will be live from the CMAs red carpet tomorrow. The show should start around four and it should be fantastic. We’ll be streaming live on Periscope, Facebook, AND ON OUTKICK ITSELF. So come hang with us. 

2. Yesterday’s Outkick the Show was a work of art, if you aren’t watching or listening to the afternoon show, I guarantee this will entertain you. Enjoy.

Okay, here we go with the anonymous mailbag:

“I have a serious problem. I am in my mid 30’s and I’ve been married for several years and have multiple kids. My wife is great, but I am a douche bag. We both have good careers and each make over six figures.

I go to a martini bar 3-5 times a week around lunch for a few drinks with my buddy. My wife has no clue this is almost a daily thing for me and she would flip out if she knew.

That’s not the bad part.

There is a hot 22 year old waitress/bartender that always serves us. We tip her well always and she flirts and is wonderful eye candy.

The problem is the past four weeks or so I have met up and got a few blow jobs from her. I know this is terrible and I feel awful, the guilt is killing me. I stopped going there last week and she texted me that she is past due on rent, blah blah blah. Basically she really needs $10k or she will go to my wife.

I see that I have three options.

1. Be honest and tell my wife the truth and tell her to fuck off. This will be horrible because my wife will go crazy and probably kill her and divorce me.

2. Tell her to fuck off and deny deny deny…

3. Pay her and pray that she leaves me the hell alone. I am worried if I pay her she will come back for more later on down the road. Thanks for your help and lesson learned here.” 

First of all, you’re missing your best option: this is extortion and it’s a crime. Whatever you do, DO NOT PAY HER. 

What I would do is text her back that what she’s doing is a crime and that you have reported her to police and shared her text messages with them. (If you have a police officer friend this is even better because you can specifically reference him.) Then I would drop the hammer and say that if she says anything to your wife that the police will arrest her because then she is following through on her extortion claim.

Now, the challenge here is if you go to police, and actually follow through on the extortion claim, then you’d eventually have to testify in a trial like Rick Pitino, which would humiliate your family and require that you fully confess to your wife. So you might want to just lie and say you went to the police, even if you didn’t. 

Will this girl call your bluff and tell your wife if you don’t pay her? I have no idea, she’s an untrustworthy 22 year old cocktail waitress who’s blowing a married dude, she’s not exactly the most reliable person on the planet. 

Neither, by the way, are you. 

Your primary goal here is to ensure that your wife doesn’t find out. And, honestly, there’s no way to ensure that doesn’t happen, which is why I’d advise telling her that extortion is a crime and that you’ve contacted police and that she’ll go to jail if she tells your wife anything.

Hopefully that will scare her into doing nothing.  

I’d then cut off all contact with her.

If she actually contacts your wife, I’d claim she’s crazy and deny everything. I’d also be tempted to get her arrested for extortion, but, again, then you have to take the stand and testify about your daily martinis and blow jobs, which is probably something you don’t want in the public record. 

Good luck. 

“My girlfriend and I have been doing a long distance relationship for a while now. With that comes sexting. I’m in college so I’ve sent a good amount of dick pics to her. This is all well and normal until one day something changed. She decided to show my dick pics to her roommate!

Now I’m not ashamed with the size of my junk but her roommate has been with her fair share of guys. Odds aren’t in my favor that it’s the best dick pic she’s ever seen.

Now whenever I’m with her roommate all I think about is “she’s for sure thinking of my penis right now.” Should I feel weirded out that she’s seen my penis? I’m not sure if I should ever drunkenly bring it up and make fun of the situation to put and end to it or what. What’s my play here?

(P.S. Asked my girlfriend for a threesome with her roommate who saw the picture, she acted like I was insane for asking.)”

The next time everyone gets drunk you bring up the dick pic by suggesting that since she’s seen your dick she owes you fair market value for your dick pic.

As you see it there are two options that constitute a fair trade for her seeing your dick pick: a. a threesome or b. she shows you her boobs.  

Either way, you win. 

Do this in front of your girlfriend so it’s clear that you’re not trying to secretly bang her hot roommate. (I’m sure you have zero interest in banging your girlfriend’s hot roommate. Wink, wink.)

If she refuses either option, who cares, you’ve addressed the penis in the room and when you and your girlfriend eventually break up, you can start texting her roommate that she owes you naked pictures. 

Also, I don’t think you have anything to worry about with the dick pic, your girlfriend was showing her friend because she was happy with your dick. No one shares naked pictures of someone they’re in a relationship with because they’re disappointed with the naked pic.

Your girlfriend thinks your dick looks great right now because she likes you. Like 95% of a woman’s satisfaction with her mate’s penis is her actually liking you. The other 5% of you just have really little dicks.  

The moment you piss her off she will decide that your penis is awful. That’s how these things work.  

“I have two children and a wonderful wife. I had a job for ten years that required travel about once a month for four days. So in a way I got a four day vacation every month.

Recently I haven’t had a trip in close to a year and I have been working “regular” hours. However, I was scheduled to go out of town next week for work for five days. Friday my boss called me and they cancelled my flight and because they do not need me to go on the trip anymore. I was really looking forward to being completely alone.

I got an email Friday evening from American Airlines for a $1,500 flight voucher from where my flight was cancelled; my boss said I keep it and use it whenever. I have not told my wife the trip was cancelled yet.

Saturday I booked a five day all inclusive trip to Cabo San Lucas, Mexico. As far as my wife knows my trip is still on. I have never cheated and I do not plan on doing anything wrong except getting drunk and eating a shit ton of food. Am I the worst husband? I feel like shit now.”

This is hysterical. 

First, if your wife finds out about this trip she’s going to assume you went to Cabo with another woman because it’s actually more believable than you going on a private five day Mexican vacation by yourself.

I’m honestly not sure she would ever believe you if she finds out and you tell her the truth and said you just want by yourself because you wanted a vacation from your family. (Although writing this story to the anonymous mailbag and getting it published before your trip is actually decent evidence in your defense. You can just point to this if she ever catches you. Also, how many married women with two kids and a husband going on a work trip soon are suspecting this might actually be their husband?

Yes, you are a bad husband, but you aren’t the worst husband.

Hell, you aren’t even the worst husband in the first three emails to the mailbag this week. At least your aren’t getting extorted by a hot 22 year old martini bar waitress who has been giving you blow jobs. This, by the way, should be every husband’s line to his wife this week. 

“Honey, I know you’re mad about (something you screwed up), but in the grand scheme of things it could be worse. I could have been getting blow jobs from a girl who is demanding $10k or she’s going to tell you about the blow jobs.”

You shouldn’t do this trip, but you know this already.

Imagine your wife’s reaction if you told her you had $1500 in free flights and you and she were going away for five days without the kids to Cabo. And you had already scheduled a babysitter for those five days and told your wife’s boss at work that she wouldn’t be there for the next five days. She would fuck you like crazy in Mexico that entire time. 

That seems like the better move. 

So if you take your solo, secret trip to Cabo, you should probably do an additional trip for your wife regardless.

That way she’ll be bragging to everyone that she has the best husband in the world. Of course, it won’t be true, but this way you get two trips.  

“My girlfriend of four years went to a party after an SEC game. So after the party she goes home and gets a drunken email (that’s right, a fucking email. Because he doesn’t have her number) from a guy who was at the party. It basically states that he would love to have lifted her dress to see what was underneath.

Now, I’m not jealous at all, in fact I take it as a compliment when someone hits on her (although she then gets mad that I’m not mad? Another topic for another day). But here is the kicker, the guy who sent it is getting married in a few weeks…. To MY BEST FRIEND’S SISTER. Now, I’m not sure if he knows she’s my girlfriend, I’ve never even met him, but I am invited to the wedding. My girlfriend says if she was getting married in two weeks she would want to know that her fiancé did something like this.

Personally, I don’t think we should bring it up, unless we tell him #dbap and say it to her face instead of sending emails. But the girlfriend insists we tell my best friend’s sister, what say you?”

I would have been so tempted to respond to this email if I was this girl by saying, “Funny you should ask. Under my dress I had on underwear. And under my underwear was my vagina.”

But let’s dive back in here. First, what kind of conversation did your girlfriend have with this dude that he sent her an EMAIL saying he would have loved to have lifted her dress to see what was underneath?

She needs to come clean here.

If it was a totally innocuous, innocent conversation then this dude is a major creep. Not only did he track down her email address, but he sent her an incredibly aggressive, sexually charged email that she didn’t invite at all. SHORTLY BEFORE HE’S GETTING MARRIED.

That seems aggressive even for a creep. He had to think that something happened between them, right?

Moreover, he didn’t just hit on her or say something inappropriate, which he could always deny, he sent it from his own email address. 

What defense does he have? The only one I can think of is he claims someone else got his phone and was pranking him with the email. In fact, that is the only possible defense he has, which is probably why that’s what he’ll claim if you tell his fiancee. But this doesn’t make sense either. So someone got your phone and looked up a random girl’s email address and sent her a sexually suggestive email?

That’s a strange prank. 

Nope, the reason this dude sent this email was the reason most dudes do anything, because in his mind this email made it more likely that he was going to have sex with a girl. (This is literally the direct motivation for 99.9% of all things that men do. Why did Neil Armstrong walk on the moon? For the pussy.) 

Now for the next part of this question: would you want to know this behavior if you were getting married? Undoubtedly, you would. And so would anyone else reading this.

So I think you have to tell her.

The problem here is, this is your best friend’s sister not your best friend.

So how do you tell her?

I think you have two options:

1. Directly tell her yourself with your girlfriend present.

But no one else should be there. And you have to tell her that you have no plans to tell anyone else, but that you think she should know. Then show her the email. 

Make it clear that you aren’t judging her or him, but that if it were one of you about to get married, you’d both want to know. 

This way she can make her own decision and doesn’t have to worry about a ton of other people knowing or judging what she does. After all, calling off a planned wedding is a big deal, even if you’ve just found out that your fiance is much different than you thought.     

2. You tell your best friend. 

I think you have to tell your best friend regardless, right? It’s his sister and his future brother-in-law. Option one requires you to keep a secret from him. What if he immediately cheats on her after the wedding, she finds out, and divorces him? Which, let’s be honest, is downright probable here. Wouldn’t you feel bad for saying nothing? So I think you have to tell him. 

My bet is he’ll probably flip out. 

If he’s anything like most brothers, he’ll immediately tell his sister. And maybe go beat his future brother-in-law’s ass too.  

Either way, if the wedding still happens, you can’t go. 

Update us on what happens. 

“I have a bit of a conundrum at hand. My best friend (practically a brother) just introduced me to his little sister last week. We’re both in the military and both got stationed back near his family. Well little sis turns out to be a total babe. That night she proceeds to give me every sign in the book that she’s into me and at the end of the night slips me her number. The problem here is that my friend has told me a story of one of his buddies trying to date his sister and it completely ruining the friendship when my friend told him he shouldn’t. Do I try and pursue this carefully or do I respect my buddy’s wishes and leave the sister be? Thanks for the words of wisdom.”

If you date his sister there are only two ways this ends:

1. You marry her, in which case this becomes awesome and you have an incredible brother-in-law and he’s ultimately excited to have you in the family.


2. You guys start sleeping together, eventually break up, and he finds out.

And then you’re just the asshole who banged his sister.  

So my advice here would be only pursue her if you think this girl could be someone you’d be willing to marry. If you just want to bang her, there are plenty of girls that aren’t your buddy’s sister to chase.  

And the way I’d advise you to find out how much you like her, not by dating, but just by engaging in phone and text conversations. 

If you decide you really like her and want to date exclusively instead of just bang, then you tell your buddy at that point and ask for his blessing. 

“My buddy has a girlfriend that he wants to break up with but he can’t get himself to. They go to colleges at two different schools and he wants to wait until Thanksgiving break to go back and break up with her.

The problem is that a group of guys here at our school, want to go up to her school, to party for a game this weekend. He wants to go, but he doesn’t want to see her, or for her to find out that he is there. The chances of her being at a tailgate or party that he is are somewhat low, but there is a chance that he sees some people that know her. Does he go?”

How in the world, in this age of social media, do you think your friend can go to the same college as his girlfriend for a weekend and her not find out he was there?

She’ll definitely know. 

So he can’t make the trip. 

That’s even if he breaks up with his girlfriend in advance of the trip. How much more of a dick can you be than break up with your girlfriend and then show up and party on her campus that same weekend? 

“Sorry to get serious, but you actually give really solid advice in the mailbag. So, here’s mine. How do you heal a broken heart? How do I move on? I’m old enough to know the type men I like, so that just means this hurts all the more because I actually found someone that I was really in love with. We clicked on all levels and he basically blindsided me. So. What do I do? Also, on the positive side, Go Cubs Go!)

The only thing that works is time.

And something to distract you from your thoughts. I’d suggest pouring your anger into working out and getting so hot that the next time you cross paths all his guy friends are going to call him an idiot for ever breaking up with you.

That’s honestly the best revenge you can get.  

Also, be glad you got blindsided before you got married instead of after. It could be worse, your boyfriend could have been emailing strange girls about wanting to look underneath their dresses. 

And, importantly, don’t buy into the idea that there’s only one person for you. That’s absurd. There are literally thousands of people in America alone that you could marry and be perfectly happy with. If you live in a big city, there are hundreds of people in that city you could marry and be happy with too.

The idea that there’s one perfect person for you in this world is total crap. 

So you will find someone else.   

“I believe the “Officer, I was speeding because I had to use the bathroom” line is old news. If you want to get out of a ticket, you can’t come with a weak story like that. 

My son was recently in the Children’s ER. For the record, he had acid reflux and we were sent home with Zantac. The Children’s ER gives out designated orange “parent” bracelets you wear so you’re quickly admitted past security. I grabbed 2 extras of these bad boys, got pulled over, showed my orange bracelet, told a brief story, and I’m on my way without incident.”


Exactly the kind of behavior I would expect from an anonymous mailbag reader. 

Send your anonymous mailbag questions, anonymity guaranteed, to

I believe the “Officer, I was speeding because I had to use the bathroom” line is old news. If you want to get out of a ticket, you can’t come with a weak story like that. 
My son was recently in the Children’s ER. For the record, he had acid reflux and we were sent home with Zantac. The Children’s ER gives out designated orange “parent” bracelets you wear so you’re quickly admitted past security. I grabbed 2 extras of these bad boys, got pulled over, showed my orange bracelet, told a brief story, and I’m on my way without incident.

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.