Anonymous Mailbag

It’s Tuesday, time for the anonymous mailbag.

The anonymous mailbag is presented by my guy Ryan Kelley at The Home Loan Expert. Own a home but also have too much credit card debt? Go to their website today and by this time next week your credit card debt can be wiped out and you can have a brand new low rate mortgage. Put your financial house in order just in time for the holiday season by wiping out your credit card debt and visiting him today Also, if you use The Home Loan Expert and tell them Outkick and Clay Travis sent you, you get a free year’s VIP subscription.

If you have any anonymous mailbag questions you can email them to, anonymity guaranteed. Okay, here we go.

“Today I was scrolling through twitter and came across an article about a vacation called “sex island” every year. Since I had never heard of it I was curious. Anyway after reading I didn’t think this could be true so I did some more research and as far as I can tell this is all legit. It’s a private island somewhere around Trinidad and Tobago where you pay a couple thousand to have unlimited sex, drugs, and alcohol for 3 or 4 days. There’s only 50 tickets available for each so called trip or weekend an each person that goes basically has two prostitutes. 

So this got me thinking, should I do this? First off let me tell you I’m 26 with no wife or girlfriend with an excellent job in a flyover state near a town that has 4,000 people in it. Safe to say entertainment is somewhat sparse around me. Closest big town is about 2 hours away.

Money really isn’t an issue as I’ve made $90k+ for the last 3 years with virtually no expenses. This is what I’m worried about, however. I’ve traveled through many airports across the US but have never been out of the country. Do you think there’s a possibility where I could get put in a situation where I have to fear for my life? Getting shot, jail, hospital, etc. is probably unlikely but also a much higher chance then traveling to let’s say, Europe. Would you agree? I thought about trying to bring a friend along but a lot of my college or old high school buddies don’t make what I make or have wives/girlfriend to where I know they would never go. What do you think? Sounds like a single guys dream but are there enough positives to outweigh the negatives?”

This Sex Island thing has gone viral. I’ve been emailed about it several times and several different guys I know have brought it up recently as well.

I was talking about it with a bunch of buddies recently and we were all debating the pros and cons of having gone when we were single. I came down on the side of it being an awesome trip, but only if you went with at least one other friend. That’s because I wouldn’t want to go by myself and just meet other guys I didn’t know at a big orgy. Now that’s partly just me in general, I’d never want to go on vacation by myself anywhere, even to a sex island.

I don’t think you need to be concerned about getting arrested — most of the places you’d go exist pretty much entirely for tourism and the worst thing they could do is arrest Americans and kill their local economy — but I do think it’s fair to worry about your privacy being yanked away somehow.

My concern was primarily that everything is being recorded and at some point you’d get outed as having gone on the trip. Either that or their customer list leaks and your name is on the Internet and everyone knows you took the trip. Maybe when you’re a single guy that’s not a big deal, but what if it leaks in ten years and you have a family by then? Or what if you end up with a prominent job and your company fires you?

Remember when the Ashley Madison subscriber list leaked? I think you have to assume that almost everything you do on the Internet is going to leak at some point. This is why I only jerk off to college girls and MILFS in porn videos. God forbid I was into some really creepy jerk off shit, I’d live in mortal peril that my GILF porn interest was one day going to be outed for everyone to see.

I’m so glad my porn interest makes me such a basic bitch, I like good looking women naked between the ages of 18 and 35.

Thank God.

But if no one knew you were going to Sex Island, there was no evidence you’d gone, and, and this is significant, you knew that STDs weren’t a threat at all because either they test all the women beforehand and ensure clean bills of health or you knew you’d always use a condom for everything, I think this is a no brainer. (Also, you wouldn’t want to get a woman pregnant. Can you imagine this? Worst. Maury, Povich. Ever. Kid: “How did you and my mom meet?” Answer: “Daddy paid a lot of money to have anonymous sex with strange women for a long weekend.” Ah, true love.)

Assuming disaster didn’t happen,  just think about it for a minute, when you were a single guy and you went on vacation to a tropical destination what were you hoping for?


You were hoping you were going to be on vacation and you would meet hot girls and you’d have a ton of no strings attached beach sex.

But then what usually happened?

You hung out with a chubby, sunburned girl from Canada and all her chubby, sunburned Canadian friends and maybe she gave you a disinterested blow job after two days of pursuit.

And that was a good trip.

The number of guys who pulled off two or three no strings attached sexual encounters with good looking women  while on a tropical vacation was really, really low.

That’s because most good looking girls in these locations are in high demand from the single guys — or already there with boyfriends — and it’s virtually impossible to turn your vacation into an orgy featuring tons of hot girls you didn’t know before you got to the vacation.

Doesn’t this just eliminate all the suspense and give you exactly what you want?

I’m honestly stunned it’s so affordable.

I know some people have hang ups when it comes to paying for sex, but I don’t. I think prostitution should be legal.

Look, all men are paying for sex in some way, this just eliminates the fakeness. She’s sleeping with you because she wants your money and you’re paying her to do it. As long as she’s making the choice to be there, it’s pure capitalism.

I don’t know why we’re fine with selling everything but sex.

Imagine if instead of there being restaurants you had to convince girls to cook for you for free if you wanted a meal outside of your house. That would be insane, right? Yet that’s what we do for sex.

If you want something, pay for it.

I’d probably go if I were a single guy in a small town with ample money like you.

“I have been happily married to my wife for almost 10 years. My wife is hot and keeps a regular grooming routine just as any lady would….
However there is one thing that has bothered me for a couple years. She has long nose hairs that stick out and are very noticeable.
To be honest they are pretty gross and detract from what otherwise would be a beautiful appearance. What I don’t get is how she doesn’t notice them? Or maybe she does and just doesn’t care??
If I come out and tell her straight up I’m afraid that she will be overly sensitive about it…but if I don’t say something I’ll be dealing with these whiskers for the rest of my life!
I ordered myself a nose hair trimmer and used it in front of her hoping she may get a hint but alas…. no hint taken. 
What should I do?”
Find a woman to broach the conversation with her.
It can be a girlfriend of yours, a sister, regardless, you need the girl to claim that she had nose hairs that she couldn’t get rid of and then she found — insert miracle cure here. That way it could get your wife thinking about her own nose hairs and how to solve her issue.
Ideally you can overhear the conversation and then bring it up later with your wife if it still doesn’t take.
Surely she has to see them, right?
My guess would be she just hates the pain of pulling nose hairs and waits for them to fall out.
The other possibility is just to directly tell her and offer to trim them for her the next time you’re using your nose hair trimmer. But that could be fairly awkward.
I don’t ever do my eyebrows, but every now and then my wife tells me my eyebrow hairs look ridiculous and she just trims them herself. I’d never know I had ridiculous eyebrow hairs if she didn’t tell me. I find it hard to believe your wife has no clue about her nose hairs, but maybe she doesn’t. Or maybe she doesn’t think anyone else notices.
So I’d try the art of subtle persuasion form another woman and if that doesn’t work, I’d just go direct.
Good luck.
“Mid 30’s couple – I’m a financial advisor and my wife is a teacher.  She desperately wants to quit her job and stay at home with our 3yo and 5mo old sons.  Financially we don’t need her to work and she nets very little after we pay for child care.  However, I work from home quite often and truthfully, don’t work very much.
I work extremely hard when I work and reward myself with less hours.  The main reason I don’t ask her to stay home is because I don’t want her to know how many days I fuck off, play golf, cocktail lunches, naps, etc.  I’m struggling with the selfishness in this but really don’t want to ruin a great thing.” 
As someone who works from home and likes the freedom of doing so, I can see your point here, even if it is extremely selfish. Here’s what you’re arguing: “I want to be able to golf and nap during the day even if it means my wife and kids are unhappier than they would be if I only golfed and napped outside of work hours.”
Plus, I don’t even think your mid-day fun would need to all be erased.
I’ll explain why, but first, I work from home every day. The difference between me and you is I work a ton of hours. In fact, the biggest challenge I have is that I never really stop working. I try to not be in my office upstairs after 12 hours a day, but even then I can get emailed or called and I’m always working on something.
Unlike you, I’ve never had a home work environment where there aren’t other people around — my older kids have always been at home and we have a four year old now who is at home — but I can imagine it’s really, really calm and peaceful for you if you’re working from home by yourself all day long. Especially if you don’t have to work that hard.
That does sound pretty fantastic.
But I think you’re overrating what your wife will know about your daily plans. If you say you have a meeting, how will she know you’re playing golf or at a movie as opposed to at that meeting? I think what you have to make clear at the outset is the idea that you work from 9-5, or whatever it is, and she needs to have the kids during those hours if she isn’t working. Because otherwise what could end up happening is you turn into a default babysitter and it keeps you from being able to get your work done.
That’s not good at all.
I think what you’ll find is your life will be infinitely better without a wife who works. She’ll be happier, the kids will be happier, and your life will be much better even if if your home work environment changes some. Plus, I think you’re underrating how much your wife will be out of the house with the kids. She’ll take them to the gym with her every day, she’ll take them to the library, they’ll go out to lunch together. She will find all sorts of things to do with your kids to get them out of the house and she won’t pay that much attention to you.
When my wife quit working it was phenomenal. I just wish we’d been able to afford to do it when my two youngest were very young. It would have been infinitely better than putting them in day care.
My favorite thing about working from home is how often I get to eat lunch with my four year old. Before that it was eating lunch with my middle son. I loved being able to come downstairs from work and eat lunch with them. I still do.  Honestly, I was disappointed when the two older ones started going to school.
Having said that, the holidays and the summer can be hellacious when you work from home. That’s because the house turns into a total zoo and I’ll be writing upstairs when I hear World World III break out over Madden or Fortnite and I have to go downstairs and keep the kids from killing each other.
But all of that pales in comparison to having a happy wife. Trust me, if you can afford for your wife not to work, do it. If she wants to quit and her entire salary is going to child care already, you should surprise her this Christmas by saying you love the idea and let her start doing it.
Your life will get better, not worse, trust me.
“So let me start by saying I work for a pretty large regional company in the Southeast. In my department I have 4 other people who work in the same position as me. We have a boss that we report to just give to some background information. 

Well Monday morning, I walk in after being gone on a work trip the previous week, a female coworker proceeds to tell me I owe $50 for our bosses Christmas gift. Now keep in mind this is the first time I have heard about this and certainly I have not agreed to do it. I really don’t want to do this as my boss probably makes more than all 5 of us combined and it seems utterly pointless to spend $250 on a gift for him. So I’m coming to the gay muslim himself for advice. Should I throw up the middle finger and refuse to pay and stick her with the bill or should I cave in and pay the $50 to keep the peace.”
It’s $50, don’t be a dickhead.
My general rule in life is this — if the money is inconsequential — and it sounds like it is in this case — worrying about the money is a bigger issue than just eliminating the stress and being done with it.
Furthermore, don’t you want to get along with your co-workers? Why create ill will by forcing them to all chip in to cover your $50? Wouldn’t this result in them leaving you off the Christmas present meaning your boss might notice it? What if your boss has to fire one person? Do you know who he might pick? The guy who didn’t chip in on his Christmas present.
Arguing about this is just a bad move, pay your share.

“Hey Clay! I’d like your opinion on alcohol and kids. More specifically, you mentioned a while back you enjoy watching sports with your children. I am with you on this. My seven year old has wanted to watch football every Saturday and Sunday this season, which is great, but this is also when I like to have a few drinks and relax.

Is this in poor taste? Should I avoid alcohol altogether when watching the game with the kids? What are your rules/protocol?

Seems like no big deal to me, but then I was told by my brother today that him and his wife do not feel comfortable bringing their kids around me anymore b/c I had a drink when they came over to my house a few months ago. Mind you, I was not even close to inebriated. Anyhow, what say you future senator?”

I think it’s fine to have drinks while you watch games with your kids as long as you don’t get noticeably drunk.

Personally, I don’t drink by myself. So I never drink when it is just me and my boys watching games together.

But my eight and ten year old’s do know more about gambling than almost any eight and ten year old’s in the country. This is what happens when your dad is on a gambling TV show.

I never knew the line on a game when I was a kid, my own kids know about live wagers, over/unders, parlays, teasers, you name it and they’re conversant in it.

Sometimes I’m terrified that I’m working so hard now so my kids can just gamble away their entire inheritance on sports.

In fact, the first thing my eight year old asked this morning when he sat down for breakfast was, “Did the Saints cover last night?”

So while I don’t drink in front of them much, I do gamble in front of them all the time.

I’ve even got them working on their math skills by doing the math on over/under game pace and whether or not we’re going to win our bets.

I’ll let you know how this turns out.

In the meantime, I think your family is overreacting by hiding their kids from you because you drink during games. Boy oh boy, are they ever going to be shocked when they go to actual games and see all the alcohol being bought there.

Your family is overreacting and you’re doing nothing wrong by drinking during games you watch with your kids.

Send your anonymous mailbag questions to, anonymity guaranteed.

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.