Anonymous Mailbag

It’s Tuesday, time for the anonymous mailbag to zap all your work productivity.

Okay, on to the mailbag.

“So you talk about watching porn a lot (for the record I watch porn every so often so I’m not necessarily anti-porn) but my question is do you and your wife ever argue about you watching porn? The one time I admitted to my wife I used to watch porn, it was an argument that nearly ended my marriage. She only wants to have sex once or twice a week but I could easily partake 4-5 times a week so some weeks I’ll fill the time gap between sessions with my wife with a porn session. I view it as emotionless orgasm but she views it as infidelity. What do you say?”

If porn is infidelity then pretty much every married man is cheating.

I honestly don’t even understand a woman’s rationale here when she makes this argument.

But in a non-judgmental fashion, I’d like for you to unpack her decision making here. You should start with this question: does she believe that masturbation is cheating? If so, at least that’s logical. Crazy, but logical. Because then she’s arguing that she has to be involved in all your ejaculations. See what I mean when I talk about unpacking the logic behind her position?

If she does believe that masturbation is cheating then quiz her about it further: would she believe that masturbation was cheating if you promised to only think about having sex with her while you masturbated? What if you had sexy photos of her to look at or a sexy video of her to watch? (Might as well make the case, right?) In other words, if she’s driving your sexual desire during masturbation it can’t be cheating, right? Whether she’s physically present or not, you’re still thinking of her.

If she still says that’s cheating, then is a wet dream cheating? Because if you never masturbated odds are — and given the infrequency of your sex life it’s pretty much guaranteed —  you’d have wet dreams occasionally. Those would involve sexual thoughts. Now, those thoughts wouldn’t be voluntary, necessarily, but it would be a sexual emission without her involved. Is a wet dream cheating? Especially since there’s not a man alive who has wet dreams about his wife alone.

Now, if she’s more logical and she doesn’t believe masturbating is cheating on her, then what about porn makes it cheating when masturbation alone isn’t? The fact that there’s another naked woman involved? What if you jerked off to sex without nudity? Does she feel differently about pictures vs. video? Is one better or worse than the other? If she considers both to be cheating, why? Because you’re wishing that you were having sex with the girl in the video? What if you just like watching two people having sex and aren’t imagining yourself having sex with the woman? (I don’t think most men watching porn are pretending it is them having sex with the woman.)

In other words, I think you need to unpack the logic behind why your wife believes she should control all of your sexual thoughts and sexual acts. Because that’s effectively what she’s doing when she says you can’t watch porn. I understand why people in relationships believe they should control the exclusive act of physically expressing yourself sexually with another person, but I just don’t understand why your spouse or significant other should control what you do by yourself. Or what you think about while you jerk off.

Honestly, if your wife is willing to divorce you over watching porn, I’m not sure you can stay married to her and ever share your true feelings about sex. Certainly there are many people who lie with their partners about sex or money or wanting children or a variety of life decisions, but I don’t think you’re going to suddenly stop masturbating so unless you lie to your wife about it I don’t see how this issue resolves itself.

If I were you, I’d just keep jerking off to porn and never talk about it with my wife again.

Unless, that is, you follow my road map of questions above. If you can keep her from getting angry, she may just realize how illogical her position is.

“I traveled for work to the city where my best friend from college lives. We scheduled to meet for dinner and drinks. The morning we were scheduled to meet up he texts me “do you mind if I bring a girl I’ve been seeing. I’m really into her and I want you to meet her.” We talk on a daily basis & about everything so I found it strange this was the first I was hearing about this mystery woman but I encouraged him to bring her and said looking forward to meeting her.

Clay, no exaggeration, when he walked into the restaurant, I thought he brought his Aunt by mistake. This woman is 10-15 years older than us minimum (we’re 25, three years out of school). Probably old enough to be our mothers honestly. Now granted, pretty attractive, very fit, nice fake titties, but the face just screamed that she’s probably 40, it was startling.

I quickly compose myself and we have a nice dinner. Couple of college inside jokes and she commented “oh you babies” further confirming that there’s some serious cougar shit going on. After the check comes, she goes to use the bathroom and he asks what I think, I am blunt and say “how old is (name omitted)?” He says “I’ve never thought to ask! Probably late 20s/early 30s.”


I call him on it and say she’s probably double our age and I hope it’s just a phase and he wanted to bang a milf. He gets extremely offended & says that he’s pretty serious about her and wants it to be a long term thing. I’m about to lose it on him but she walks back, the two of them walk out. I have not heard from him since & we typically talk everyday. Who is in the wrong here? Do I need to apologize?”

Okay, I just don’t buy the fact that your buddy hasn’t asked how old the woman he’s dating is. That’s a clear lie. I don’t care who you are or who you are dating, the person’s age comes up pretty quickly as part of that process. And that’s even if you’re around the same age; there’s no way you date a woman or man much older than you are and don’t know his or her age. Even if you don’t ask, wouldn’t you see it on their social media profiles.

Now I remember being 25. When you’re 25 you think it’s a MASSIVE deal if someone is thirty. Five years might as well be fifteen years at that age.

I’m 39 years old now so someone being 44 or 34 doesn’t seem like much of an age difference to me. The older you get the less difference five years makes.

But if you’re 25, the difference between someone being 20 and 30, in your mind at least, is night and day.

The bigger issue than age, I think, is life experience. Has your buddy’s new milf been married before? Does she have kids? What kind of job does she have? It doesn’t surprise me that a 35 or a 40 year old and a 25 year old can like each other — by the way, trust me, if your buddy was forty and he showed up for dinner with a smoking hot 25 year old you would be jealous as hell — but I do think their respective lifestyles could be very different.

So I’d call your buddy up and tell him you didn’t mean to insult the woman he’s dating. I’d tell him you thought she was really hot, seemed cool, make it clear you aren’t attacking him or her. Tell him that you were just surprised because you were expecting someone around the same age as the two of you and her age was what jumped out at you the most. Then I’d follow up with the bigger questions and claim that was what you meant when you referenced her age. Namely, what’s her lifestyle situation? Has she been married, does she want kids, things like that. And if you really want to shake your buddy out of his milf fixation, ask him if he wants to have kids. If the answer is yes, does he want to have kids IMMEDIATELY?

Because if you’re 25 and dating a 35 year old, that’s a real consideration. Your average 25 year old guy probably hasn’t even thought about something such as that. But he should, especially if he’s thinking about getting into a serious relationship with her.

I’d also point out that your buddy may want this to be a serious relationship, but does the woman? She might be looking at your friend as a boytoy allowing her to focus on something other than a serious relationship. Your friend has only been out of college three years, make sure he’s not diving full on into a relationship this older woman just sees as a fling.

Regardless, I do think you should reach out and patch things up with your best friend. Blame the fact that you weren’t expecting the woman he’s dating now to be so much different than the girls you were around for most of your college and early post-college life.

Finally, and I can’t impress this upon all you knuckleheads reading this enough, DATE YOUNG, HOT, SINGLE WOMEN WHILE YOU CAN!

There will be plenty of time in your lives to date divorcees and milfs. Why do it when you’re 25? Especially when you’re doing it, as seems the case here, looking to have a serious relationship. Chase young girls while you’re young. Because it’s much easier to catch them then.

“We had my five year old’s birthday party at a climbing gym over the weekend. One kid from the daycare came with his dad that we’d never met. All the kids were having a blast, that is, until the unknown Dad started yelling like a drill sergeant at his poor four year old son.

Then it got worse the entire party went silent as he pinned his son up on the wall in the air and wouldn’t let him down. It was so awkward. We didn’t intervene but obviously wanted the guy to leave. What’s the proper protocol here as the party host? Is it appropriate for me to pull the guy aside if I ever see him at the daycare?”

First of all, I feel awful for the four year old.

Because my fear is always if the dad is comfortable doing this in public — holding a kid pressed up against the wall and screaming at him — what would he do in private? Maybe it’s the same borderline behavior, but I tend to believe the behavior is worse in private.

That is, parents are trying to do a better job of parenting when they know everyone is watching. This guy is probably much worse when no one is watching.

And, look, I have three kids. One of them is a total hellion who regularly drives his mom and I insane. IN FACT, I JUST HAD TO STOP THE MAILBAG TO TELL HIM TO STOP FIGHTING WITH HIS BROTHER. So if you saw us yelling at him for something he’d done, you might think our behavior was out of line, but it has been my experience that most parents get angry at their children not when they do one thing wrong, but WHEN THEY CONTINUE TO DO THE SAME THINGS WRONG OVER AND OVER AGAIN AND EVENTUALLY YOU LOSE YOUR MIND WITH THEM BECAUSE THEY WON’T FUCKING LISTEN TO YOU AND STOP BEING SUCH ASSHOLES!

Sorry, I’m a little worked up here.

Having said all of that, I rarely raise my voice with my kids and none of my three kids have ever been spanked by anyone. This isn’t some newfangled thing, my parents didn’t spank me either and I ended up a saint. So why mess with success?

But here’s the deal, I have never, ever gotten involved in another parent’s parenting decision. And unless you believe there is child abuse going on, I think that’s the right call. If you do believe child abuse is going on, I don’t think you confronting the parent is going to change anything, I think you need to report it to authorities or, better, ask your day care workers to pay attention to things and see if they agree with you and can report it themselves.

Whatever choice you make, having a conversation isn’t going to help things at all. No parent has ever said, “You know what, that guy I’ve known for two hours got me to change my entire parenting style based on what he told me in five minutes at day care.”

If anything, I think you’re more likely to make it worse.

“Clay, I need major advice. I’m 28. Here’s the situation: my girlfriend of 4 plus years, fiancée of one year, just called it off. Sucks as it’s my best friend. She just took a job over the last few days in another city, came back from visiting that city, and sprung how she was feeling on me.

Here’s where I need help.

What do I do next? I live in the midwestern city that just lost its football team. I am not from here. All of our friends are mutual friends I don’t wanna stay here and don’t wanna follow her. I have a grand to my name, 6 figures in student loans and various other debts, including her engagement ring. of about $35k. How and where do I start over? Needs to be warm. San Diego would be ideal but how the hell do I swing that? I am an elementary school teacher with a doctorate in leadership. Work shouldn’t be hard. Help me out you gay Muslim.”

First, she should give you back the engagement ring and you should be able to sell it and recoup some of your money here and use that to pay off some of your debt. (You could also keep it for a future engagement if you aren’t getting fair value for it.) Every state has a different ruling on the law of engagement rings, but in Missouri you can get the ring back if she breaks off the engagement and the wedding never happens.

That’s exactly what happened here.

As a general rule I think a woman should always give the ring back when she breaks off the engagement so I’d hope she’d do so here. If not, you can threaten her and the law is on your side. (The law, increasingly in most jurisdictions, is of the belief that an engagement ring is given as a gift conditioned on eventual marriage. So that if the eventual marriage doesn’t happen, the ring goes back to the buyer, regardless of the reason why the marriage didn’t happen).

Second, I wouldn’t move until you’ve found a new job.

Use the broken engagement as an excuse to take a couple of trips to explore the cities that you’re interested in moving to. While you may feel pressure to move immediately, I wouldn’t quit my job until I’d found one to replace it. After all, your debt situation is fairly substantial given your income so you need to find a city that you can afford to live and work in. That’s why getting the ring back would be my first focus and the move would be my second focus.

If it’s any consolation, I actually think your fiancee moving to a new city will help you out. At least this way you won’t run into her around the city. Having said that, I totally understand your desire for a new start. I just wouldn’t rush into anything in terms of a move.

Good luck on your move.

“I am a corporate pilot in the Atlanta area and am often traveling, accruing hotel points continuously.  With all my hotel points I had this idea that with the Super Bowl coming into Atlanta, I could use some of my points to book a great hotel room within a short distance to Mercedes-Benz Stadium and try and find a way to sell the reservation for mega cash online (as of my last check before all rooms were sold out, most rooms were about $800/night). 

Some of my friends are leery of the idea because they say you never know who you will get in the room, and even if they use their credit card for incidentals, that there is always a chance that the hotel could come back to me to recoup any losses they might have if the people were to burn down the hotel or something!? What are your thoughts, am I a genius or am I setting myself up for ruin? Also, if you choose genius, what are some suggestions about how to sell the reservation online?”

First, you’re violating the hotel’s policies by transferring a room to someone else without the hotel’s consent or knowledge. I’m not sure of the complexities that could be involved here, but typically when you check in they ask for your credit card or a driver’s license to confirm the room is in your name.

Can you check into a hotel room without your name on the reservation or having your name left at the desk? I think that’s doubtful.

The only thing I can think you could do is call the front desk and give them the name of the person checking in and tell the front desk that you’ll be arriving later and this person is staying in the room with you. I’m assuming that’s what you’d do. (That person would then provide a credit card for incidentals.)

Essentially, you’re scalping a hotel room like you’d scalp a ticket. You have a reservation to stay in a room which you believe is worth much more than the cost. So you try to scalp your hotel room.

But what does scalping rely on? Trust. So the first question you have to ask yourself is this: what kind of person is going to get on a random website and go through this charade just to get a hotel room? I don’t think it’s going to be the kind of person paying $800 for a hotel room. If I desperately needed a place to stay and had that kind of cash to spend why wouldn’t I just rent out someone’s home through AirBNB?

Here’s the other kicker in my Super Bowl experience — it usually doesn’t end up being that hard to get a hotel room by the time the Super Bowl gets closer. The bigger the city the even more the case this  is. That’s because the two teams playing in the game end up mattering a great deal, but so does the overall size of the hotel marketplace. Atlanta has a ton of hotel rooms and what if, for instance, the Falcons, Saints, Panthers, Titans, Jags, or Bucs made the game? What if two of these teams did? I know, I know, that’s a bunch of long suffering fan bases, but many of those fans, if they could afford to buy tickets, would save money by driving into Atlanta on the day of the game and then drive back out after the game. Or they’d just want a hotel room for one night.

Atlanta isn’t Los Angeles or San Francisco, a ton of east coast teams can make a relatively easy driving trip to the town for the game.

The SEC title game is a big game every year and there’s never a shortage of rooms. That’s because not that many people come and stay multiple days.

In other words, the forecast demand can end up being much less than you anticipated and you might get stuck with the rooms.

Finally, if the hotel found out you did this, they could kick the other person out of the room and probably exert some penalty — through their rewards program — upon you. And for what reward?

You’re a pilot, that means you probably make around $150k a year.

If everything goes perfect here, you make, what $3k? I mean that’s nice money to have, but is it really going to change your year?

I just think your reward here, even if the risk isn’t very high, isn’t very substantial and not worth the time and effort required.

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.


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