Anonymous Mailbag

It’s Tuesday, time for the anonymous mailbag. Send your anonymous mailbag questions to, anonymity guaranteed.

As always, the anonymous mailbag is brought to you by the fine folks at If you need a mortgage, are shopping for a new home and want to prequalify, or have a mortgage rate in the 4’s or higher you need to refi with them. Plus, you get a free Outkick VIP membership for the year if you get your mortgage with them.

We are continuing our tour of SEC football tailgates with The Home Loan Expert and this past week the crew was in Aggieland for South Carolina at Texas A&M and this was the result:

One other bit of news, I will be doing a live Outkick Show at Zanies on Thursday night at 7:30. There aren’t many tickets left so go ahead and buy these tickets so we’re officially sold out and I don’t have to link this any more times.

Also, if you’re an Outkick VIP member we are having an event in St. Louis on Friday night so check the message board for those details.

Finally, I will be speaking in Birmingham on Monday at their Quarterback Club. So we’ve got a bunch of events upcoming in the next several days.

With all that in mind, here comes the anonymous mailbag.

“My roommate, a mid-twenties, single guy with a little lack of direction is home one morning (his birthday of all days) when he gets a friend request on Facebook from an easy 10, smokeshow that he has a mutual friend with. So, since they have a mutual friend, it passes the “this is probably a creepy old dude” test and he accepts, at which point the dime-piece starts to message him and then starts a nude video chat with him. Roommate of course obliges hot, naked chick and gives it back to her, at which point a screen shot is taken of my boy’s junk, and posted on his Facebook wall.
He, of course freaks out, deletes the person, tries to hide the post from his wall, and get this, is messaged by a random dude asking for money or his dick is going to be all over the internet. I talk him down, telling him how there has got to be thousands of hot dogs on the internet, his being another is no biggie, and it blows over. 
The questions posed to you following this are, one) how often do you think guys shell out cash for this? I imagine the guy who asks for the ransom has had some success in the past. Two) In this day and age, the conversation we have to have with our adolescent kids is truly evolving into something crazy. When and what are you going to tell your boys as they are passing into the teenage years?”
Holy shit.
There are so many guys reading this right now that are absolutely terrified of this story.
My first thought when I heard this was how is every athlete in America not falling for this and getting scammed? Think of the number of smoking hot chicks trying to bang them on Instagram, Facebook, Snapchat and Twitter every day. That’s awesome, but it also means it has never been easier to get scammed like this. I’d think every athlete in America would be naked online by now.
In general, your buddy should have known that random hot girls don’t decide to friend request normal dudes and then get naked for them online. So should all of you reading this right now. If you’re not rich and famous, you aren’t that impressive to any girl no matter how good looking you are, how cool your apartment pool is, or how awesome your car is.
Having said that, it doesn’t surprise me at all that a guy in his 20’s (or 30’s, 40’s or 50’s or 60’s or 70’s or 80’s) would fall for this. Men are incredibly dumb when it comes to sex with attractive women. By the way, how awesome is this graphic from the Sunday New York Times. What age woman do men find attractive based on their own age from 20-50? It’s basically a straight line, 20 year old women. (The women graphic was right next to it and women mostly find men around their own age to be the most attractive).

My second thought on this is that you should go to prison if you are trying to scam people this way. I mean, 100% without a shadow of a doubt go to prison. This is extortion and it’s probably occurring across state lines which would make it a federal offense. Instead of trying to bust basketball coaches for paying for top recruits the FBI should be looking into this because it’s an infinitely bigger issue of fraud.
And if it happened to your buddy, it’s probably happening to guys all over the country. It’s an easy scam to run, have a really hot girl — who probably would be working as a stripper or a web cam girl otherwise — have a steamy webcam session with a target, get him naked too, and then extort him for money after you take his picture. It’s not like the girl being naked cares if you have pictures of her. She gets naked professionally so you have no mutuality of risk like you would in most shared nudity situations. So this scam requires that an extorted dude electronically wires you the money to avoid having his pictures go up online. (The scary thing about this isn’t just your picture going up online, it’s that in theory they know your name and info so they could make this the number one Google result when your name is searched).
Most guys are never going to contact authorities about this scam because they’re too humiliated by the entire encounter.
Honestly, if I were in my mid-20’s and fell victim to this I probably would have paid the ransom. God forbid a married guy gets sucked into this, there’s no telling how much you could extort from him to avoid his wife and family finding out he was jerking off to a naked random hot girl online.
Seriously, these people should be prosecuted to the fullest extent of the law. (Of course they are probably from outside the country which makes this the perfect scam. They are probably beyond the reach of our laws.)
As for what I’m going to tell my boys, I already worry about this. Boys ages 13-18 are the dumbest creatures ever made that believe they are actually brilliant. It’s a wonder any teenage boy ever survives into adulthood, you’re just a total fucking idiot. As I say all the time, no woman in recorded history has ever died after her two last words were, “Watch this,” it happens to men all the time.
I’m going to avoid giving my boys phones for as long as I possibly can and then I’m going to hope my wife is smart enough to set up their social media accounts so we have access to all of it.
Anyway, let this be a lesson to everyone out there accepting friend requests from random hot chicks on social media, don’t get naked with them online until you’ve at least met them in person.
“I am a third-year law student in Dumpster Fire, Tennessee where we believe in lining up in the shotgun and passing the ball from the 1-yard line and get beat worse than in any game since 1905.  CAN WE PLEASE FIRE THIS MAN!  To my question….
I am turning 26 in a few months and as we all know, this means that I will no longer be covered under my parent’s bomb ass health insurance plan.  For someone who likes to binge drink and aggressively participate in rec league sports, not being covered by health insurance is a dangerous choice.  I’ve done some research and looked at some various options, but one idea keeps resurfacing as what seems like the most economical idea.
My roommate, a straight white male like myself, is a state employee.  He has great health insurance.  If he had a spouse, his spouse would be covered by his great health insurance.  However, neither of us have spouses because we like entertaining a variety of women entirely too much…..since you’re the Honorable Gay Muslim, I have to ask…
As a straight white male, would it be gay for me to legally marry my roommate, a straight white male, in order to be covered by his health insurance?
If it wouldn’t be gay, then would it be legal or would I be risking some sort of insurance fraud?…I’ve seen the movie Chuck & Larry and I’m not trying to go down that route….
Since we obviously aren’t going to consummate the marriage, then the process of having it annulled once I become licensed and get a job with health insurance benefits would be relatively quick and easy right?”
First, it’s definitely not gay.

Second, I’m not an expert in insurance fraud, but this seems like it has to be insurance fraud.

Having said that, how aggressively can you actually be quizzed about your sexual relationship with your roommate if an insurance agent thinks you’re committing insurance fraud? Isn’t it considered offensive now to question anyone’s sexual identity? I mean, if you cut your dick off and hold it up in front of the Tennessee Law School while announcing you are now a woman I think they’d have to make a statue of you holding your dick in your hand and rename the law school after you.

So I love the idea of you guys getting married at the courthouse and then getting divorced when you get a job and are covered at your new job. It’s an amazing story if nothing else. I honestly think your, “I married a dude to get health insurance in law school,” is such a great story to use at bars while picking up girls that it’s likely to get you laid at least four or five more times than not marrying a guy would have.

Having said all of this, shouldn’t you be able to get decent health coverage as a law student? When I was in law school I was covered by Vanderbilt school insurance for all three years and I think most other students were as well. So if you haven’t taken advantage of that option, I’d look into whether you can add it on when your coverage on your parent’s plan expires.

It seems easier and less time consuming.

“I definitely outkicked my coverage, married a dime who is also an incredible mother to our 1 year old son. A few months ago, she was offered a promotion with her company which entailed a move across country. Long story short, it ended up with me quitting my job to become a full time stay at home dad. My question is: why aren’t more dads doing this? It’s way better than wearing a suit and tie and going to the office every day, you score huge brownie points with the mother in law, and best of all you get to hang out with your kid all day. Plus it’s the ultimate proof that you hate all the “isms” more than anyone else.”

We’ve gotten a ton of questions from stay at home dads in the mailbags over the past couple of years.

And my answer has always been the same — if your wife is going to make way more money than you it would be really dumb for you to expect her to give up her job so you can keep your shitty job.

Personally, I’d rather work than stay home with my kids — they would drive me insane if I had them all day — but if you enjoy it, go for it.

“My wife for years has wanted to visit the Big Apple. I’ve gone several times before we were married, but with work and kids and a preference for the beach I’ve never been interested. I prefer plenty other cities to NYC and the cost, headache and, since our kidless vacation is in the winter, the temperature keeps me away. But the wife is starting to bargain and as we know the way to bargain with your husband is with sex.
We actually have a very good sex life, so she can’t just bribe me with a couple of bjs. She knows that for such a trip she has to go over the top on her offer. So my conservative, yet sexy wife has offered to wear a shorter-than-she-likes dress for a night on the town (lots of leg, lots of cleavage), strip to undergarments in the hotel hallway as she walks back to our room (a longtime fantasy of mine), and perform sundry debaucheries in the bedroom that I won’t mention to you, you pervy 1st Amendment/boob hound.
This all sounds well and good, but I’m suspicious that she’ll back out of the deal once we’re there. She made an extravagant promise to get me to buy the (extravagant) couch she wanted and never put- I mean, never paid out, so there is a precedent for this. My question is, should I role the dice and pay for a vacation I don’t want to go on, doing a bunch of things I don’t want to do for a big fantasy sex pay-out? Is there anyway you can write up a binding contract that I can make her sign? This could be a budding business for you. Thanks for the help.”
Here’s what I think you do — you take her favorite pair of shoes or her favorite dress that she’s not taking to New York City and you hold it as collateral to ensure that she fulfills her end of the bargain.
Every woman loves her favorite pair of shoes and her favorite dress more than she loves her husband or her children. Most of them won’t admit this publicly, but it’s true.
If she refuses to follow through then you keep her possessions until she fulfills her end of the bargain.
Plus, let’s be honest, New York City is a pretty fun spot for a vacation, especially without kids. The only part I 100% agree with you on is I won’t take vacations to places where it’s colder than where I am already. This defeats the entire purpose of a vacation.
The only reason to take a winter vacation is to go somewhere warmer.
The flip side of this is also true, by the way. I don’t understand all these people out there that decide to go to Mexico in July. What the fuck? Why would you go to a beach resort when it’s already hot as balls where you are now? Just total stupidity. And shut up with your, “That’s when the kids aren’t in school,” talk.
Look, my kids are in elementary school right now. I just take them out of school for our trips. We go away in February right after the Super Bowl because that’s when I can take a vacation. Whose schedule should you build around? The guy with fourteen jobs who gets up at 4 AM every morning or the kids missing the trip to the sheep farm in first grade?
Plus, if missing a week of first or fourth grade is going to screw your kid’s scholastic achievement then your kid is already an idiot and is going to end up in jail anyway. You might as well have your vacation fun now because visiting the prison on your free weekends is going to suck.
Enjoy New York City.
(And I’d suggest hiding your wife’s favorite shoes and/or dress at your office because if you hide it in your house your wife will just find it. You can’t hide anything from a woman in the house. She finds it in like ten minutes.)
“I just got back from a trip to Las Vegas this past weekend with a group of friends. They brought along another friend from out of town that I’d never met and we quickly hit it off. She’s pretty shy and didn’t want our mutual friends to find out and talk, but I was finally able to get her to go to my room with me on the second night (or rather, morning). 
Things were progressing slower than a drunken Vegas hookup should, so I decided to do what any good man would do and resort to shameless flattery. 
I came up with the very original, “I love your boobs.” 
Without missing a beat she says, “And the First Amendment?” 
I will take to my grave that not once had Outkick been discussed the entire weekend, and I just had a girl make an Outkick reference in the bedroom at 8am on a Sunday morning in Vegas. I didn’t even care that she didn’t end up fucking me. 
I should have taken her to the wedding chapel right then and there, shouldn’t I have?”
God bless her.
Yes, you blew it, completely and totally.
But this is just more evidence of how Outkick is taking over the country.
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.