Anonymous Mailbag

Charlotte McKinney, Kliff Kingsbury

It’s Tuesday, time for the anonymous mailbag. 

As always you can email any questions to, full anonymity guaranteed. 

Let’s roll. 

“What percentage of men do you think have paid for sex before?

I had my first escort encounter this weekend and have not been able to shake this moral hangover. I honestly don’t know when I will either, as it was the worst decision i’ve ever made drunk or sober. I couldn’t even go through with it once she got to my house (yes, I told her to come to the house) and the reality of the situation began to set in. I paid her the money and told her I was sorry for wasting her time. It’s only a Class B misdemeanor here, but I would have lost my gf and my job – the two most important things in my life right now. Now, I am paranoid that this escort knows my address and will just show up at the most inopportune times to squeeze easy money out of me. Obviously, I am stupid, but am I also crazy for being afraid that my life is still in jeopardy?”

I think lots of men have paid for sex. And many more would pay for sex if they weren’t terrified of getting arrested for paying for sex. Short of child porn or killing someone is there anything that’s worse to get arrested for than paying for sex? I don’t think so.

But have you seen the number of women employed in the sex industry in Las Vegas? Those women have those jobs because the market is so huge. It’s hard to approximate how many men have paid for sex because everybody lies about sex, but let’s go with an over/under of 33% of men have paid for actual sex. If you’re a pro athlete, remarkably, that percentage goes to like 90%.   

And if you define “paying for sex” broadly enough, every man on earth has paid for sex. Was that grand you dropped at the strip club on lap dances and a bottle of champagne that ended with a hand job paying for sex? Or do you think the stripper just couldn’t resist your spectacular penis and probably would have done it for free? What about that fancy overnight trip you took your girlfriend of a couple of months on? That cruise? The new jewelry?

I mean, let’s be honest, if sex doesn’t exist how many men ever get married? Some do, but most don’t, right? You could still be really good friends with a girl, best friends even, but would you risk half your assets on your best guy friend? Commit to being his roommate for life? No way, right?

From a purely economic perspective sex is a valuable commodity with substantial value. That’s why I’m on the record for believing that prostitution — as it is in many parts of the country — should be legal, regulated, and taxed. Readers of Outkick will know that I’m also in favor of legalizing most drugs and gambling. Basically, if it’s happening already I’d rather tax and legalize it than have my tax dollars spent trying to keep it from happening. That’s doubly stupid.  

As for your personal situation — yes, you are crazy for believing that your life is still in jeopardy and that the prostitute will extort you. You didn’t do anything. You went right to the brink, but you pulled back.

And even if you had paid for sex, I’d advise you to get over it. 

Remember, we don’t judge here. 


I don’t want to make this too long but with all the bachelor/bachelorette party emails recently I have to ask… What do you think the over under is on men/women cheating on their fiancée’s during their bachelor/bachelorette parties?

I’m recently engaged and while my fiancée and I are both well rounded sexually. For instance, I might have had group sex before. While he will swear up and down that this doesn’t bother him I know it does.

Basically, my conundrum is this… hook up over my bachelorette weekend and never worry about what he did because we’ll both be even or behave and hope he does too. Any advice would be helpful. Feel free to ask your wife’s opinion I’d love to see how a grownup feels about this.” 

I actually think the number of people who cheat at their bachelor or bachelorette parties is a fairly low percentage, like 20%. The reason is two fold: 1. I think most don’t want to cheat and 2. There are members of the bride/groom’s family or friends who are often at the parties. Can you really bang a stripper with your future brother-in-law or sister-in-law there? And if future family members aren’t there, it’s still likely that the bride or groom has friends at the party that might talk.  

This may be crazy, but based on your email I’m a guy who comes up with solutions.

You say you’ve been involved in group sex before. 

If you’re really worried about what might happen at the parties, how about both of you agree to give up the bachelor and bachelorette parties, you hire a hot stripper/escort, and hook up with her while he watches? 

Trust me, this is probably much hotter than his bachelor party would be. 

(By the way, my one bit of advice for bachelor parties, don’t go to a strip club. Hire strippers to come to you. It’s much cheaper and more entertaining. I didn’t know this when I started gonig to bachelor parties a decade ago. Consider this the advice of a veteran).

“My girlfriend and I just broke up after 2 years of dating since very early into college. I am going into my junior year at (SEC school) and this will be the first time since the beginning of college that I’ve been single. I’m living in a city now but soon I’ll be back at school. I plan to live it up when I get back and get with all the girls I wanted to get with while I had a girlfriend. Any tips on being a single guy in college and how to make my time being single count before I’m back in a relationship?”

I think that anyone who is in a serious relationship in college is a total idiot. 

I mean this. 

You will never have better options and less responsibility in your life than while you are at college. Why would anyone want the responsibility of an actual relationship?

I had a girlfriend my senior year of college — she was great — but in retrospect I was a total idiot for doing that. If I could go back in time and change one decision I made in college it would be that one. I should have never had a girlfriend.

I left so much fun on the table.  

You will have plenty of time for relationships after college. Don’t spend the time and effort on them now.

Trust me, most of you will end up feeling the same way. 

“Ever since I spotted you in all your gay Muslim glory at the downtown YMCA in Nashville, my boyfriend and I have been trying to come up with something worthy enough to write you about (he is an avid reader and fan. He was sweating profusely with you nearby.)

So finally we had a conversation that I felt needed your opinion.

We’re driving along, talking about cheating on each other (other couples do this, right?) and trying to figure out how fame comes into play with cheating. How much fame must a celebrity possess for it to be an automatic free pass?

He says, “I’d let you fuck Arsenal’s Aaron Ramsey,” and I tell him, “I’d let you fuck Lebron James.” (He would actually probably fight me for Aaron Ramsey and let me take the exceptionally average D of LBJ. This is besides the point.)

He drops a truth bomb that he would fuck Queen Latifah. I am disturbed by this. Should I theoretically let my boyfriend lay it down on The Queen? Does Queen Latifah qualify for having enough fame for me to allow this to slide? Isn’t she gay? Does this matter? Would your wife let you fuck Queen Latifah?

Thanks. See you at the Y soon. (Can’t you afford a better gym?)”

So out of nowhere I just texted my wife: “Would you be okay with me fucking Queen Latifah?”

All she texted back was, “No.”

I think fame definitely factors in here. But I think there’s a fame hotness/coolness scale that you also have to analyze as well. 

For instance, if Justin Timberlake wanted to bang my wife, I’d be totally fine with it. Same with Tim Riggins or Jon Snow or Dwayne Johnson or Matthew McConaughey. Those guys are all famous, but they’re also badasses.

Fame isn’t enough. For instance, if Senator Ted Cruz or Governor Chris Christie wanted to bang my wife, I’d be like, “No way.” And those guys are running for President. 

Queen Latifah is an extremely borderline candidate. She’s 45 years old, not particularly hot and not particularly famous. I think the litmus test here is how would other people respond if your significant other banged this person? Like, if your boyfriend banged Jessica Alba, everyone would think, “Wow, good for him.” 

Just like if you banged Justin Timberlake, your boyfriend’s friends — the ones who didn’t suck anyway — would all be like, “Good for her. I’m jealous.”

But how does everyone respond to Queen Latifah?

I mean, it’s a really funny story — sort of like banging Hillary Clinton would be a funny story, would you let your boyfriend bang Hillary? — but no one’s impressed by it. The badass/fame scale isn’t in play. Plus, if your boyfriend would bang Hillary or Queen Latifah, who wouldn’t he bang? There has to be some measure of selectivity at play here. Otherwise it’s just a free for all.

And next thing you know you’re banging Rick Reilly.   

“Big fan of the website since day one. Need your help. My wife and I very rarely have sex (just once this year). We/she have a pretty valid reason, we have 14-month old twins so our time, opportunities, energy, etc… are limited. That being said, what’s the minimum a married couple should have sex regardless of the circumstances? I understand us both being busy and her being exhausted, but once every 6 months is crazy, right?!

I value your opinion mostly because I showed her an article of yours talking about a BJ coupon book and she actually ended up giving me a book containing 12 free BJs for Christmas last year. Needless to say I have a fantastic wife, despite the fact we don’t have sex.

Your gay.”

Look, I get that kids — twins especially — make your day really busy, but how long does it take to have sex? We’re not talking about running a marathon here. Ten minutes, maybe? That’s almost less time than it takes your wife to brush her teeth, floss, and wash her face, something that most women do every night without thinking about how much time it takes. 

Here’s my relationship advice to women that will be infinitely more valuable than the thousands of hours you spend analyzing your relationship every year — fuck your husband three times a week. (If you already do that, more power to you. But if you don’t — and most married women don’t — just try this for three months and tell me that things aren’t better in your relationship.) 

“One of my best friends is getting married. (God rest his soul). Last weekend for his bachelor party we went to Gatlinburg for a weekend of drinking and golf. I was the only single guy on the trip.

While getting drunk on moonshine samples, which is a real thing, we met a bachelorette party. They were cute, but all either engaged or married.

We went upstairs to a restaurant and hung out even more. They were fun and pretty cute. All graduates from (SEC school.) After buying several drinks for the bachelorette, she says to me “I’m so horny, if you buy me a couple more drinks I’ll come home with you. I need to get laid.” I guess I’m kind of smooth sometimes but I didn’t know what to do really.

So I bought us another round.

I think she’d have come home with me if her sober friend hadn’t been there, and I would have done it. So, am I an awful person for trying to bang a chick who is now married?” 

Sleep easy, that’s on her, not you. 

As always, 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.