Anonymous Mailbag

It’s Tuesday!

Time for the anonymous mailbag.

You can go win $10k of my money this week with our free Outkick college football pick’em.

Go play. (I hope you all lose).

In the meantime, here we go with the anonymous mailbag.

As always you can send your anonymous mailbag questions to, anonymity guaranteed.

“Clay, I’ve been married for a few years and the other night I went to happy hour with a female coworker (same department, different team) who I’ve been friends with for many years. Attractive, very easy to talk to. We’ve grabbed drinks in the past before but this was actually the first time it was just the two of us. It started off typical – sharing work complaints, etc, but took an interesting turn.

As the evening went on she became a little touchy and told me her goal was to have sex in one of the conference rooms. She didn’t outright proposition me but it was brought up on multiple occasions. I just laughed it off each time, but don’t get me wrong this is an act I’d be very interested in having. I enjoy the thrill of having sex in public places and I’d be a liar if I said I wasn’t a bit intrigued. I hold my marriage & profession in a high regard, but am I wrong for having an interest here and feeling a bit conflicted?”

Your question to me is: should you, a married man, have sex with a female co-worker you aren’t married to on a conference room table at work?

The answer is clearly no.

Do I understand why you would want to have sex with a hot co-worker you aren’t married to on a conference room table at work?

Of course.

But leaving aside the morality angle much of life is about analyzing risk and reward.

So let’s simply analyze the risk and reward.

The reward is you have incredible sex with a hot girl you’ve never slept with before on a conference room table at work. That reward lasts for, what, fifteen minutes at the absolute most? (Probably five minutes, but let’s pretend you last a little while here.) Sure, you get to relive the experience in your mind, but the actual tangible enjoyable sex is twenty minutes at most. To be fair, you probably get to have sex with the co-worker again too so I won’t leave that part out.

So that’s your reward.

Okay, what’s the risk here? Your wife, your job, and, potentially, a #metoo issue that could make getting employed again more difficult as well.

So the question you’re essentially asking is should I risk my wife and my job for twenty minutes of sex with a co-worker?

The answer, at least if you like either your wife or your job, is clearly no if you just analyze this from a pure risk and reward perspective.

Your risk is far greater than your reward here.

What you’re hoping for is you get to have no strings attached sex with a co-worker on a conference room table at work, there are no complications that arise, and your work and your wife never finds out.

Is that possible? Sure. Maybe it’s even more likely than not you could get away with it.

But what are the chances you have an issue and get caught by either your work or your wife? Fairly decent.

It just seems like too risky of a move to me with a relatively modest payoff.

“So this year I got roped into going on a cruise with my fiancée at the time and her parents and her whole family. It was my first cruise and I fear heights so I was already not at my best on the trip, but having 2 kids in our room (one mine and one not), and having to adhere to her mother’s constant need to be in charge and push us to do things I didn’t want to do, it was not the best experience overall.

It was very stressful and we got into almost daily arguments with each other and instead of the vacation making our relationship stronger, it hurt it temporarily. My fiancée and I then decided to get married this summer and I surprised her with another cruise, with just the two of us.

It was expensive as can be since it was in mid-summer (almost $4000 including excursions, gifts for family, drink plan to booze it up for a week, and base cost of cruise, etc), but we had an amazing time as my family watched our son. This was also the FIRST vacation my wife had been on without her parents and we are in our 30s.

Fast forward to the present…we are planning one for next year in the spring. I find the perfect cruise, get the ok from my mother to watch our son again, and think we are set. WRONG! Her mother again must be involved with everything in our lives and is inviting herself and her husband on the voyage to be determined. Then on top of that they want to bring the whole family again and there would be a kid in our room (not mine) so we can pretty much rule out any intimacy on the cruise. And if I’m going to have to have a child in our room, why am I putting it on my parents to watch our two year old son for 8 days? We might as well just bring him along on the cruise as well like the first cruise from this year so at least my parents can get some alone time!

I was under the impression last year’s family affair would be a once a 4-5 years’ type vacation and I feel that is fair. I am to the point where I just don’t even want to blow $2,500 on this cruise (would be less if we didn’t get the drink plan but with in-laws present that seems a requirement), and just stay at home on my days off and save money and pay off bills. That said, I am tempted to find the most expensive cruise next summer and go on it in hopes of it out budgeting the above plot by the mother in law as they would have to pay for 5 people against just my two. 14-day cruise around the Panama Canal anyone? I jest as we are not financially to the point that we can afford another 4,000+ dollar vacation every year.

Am I being completely out of line not wanting to allow this for a second year in a row? How should I handle this monster-in-law situation?”

You need to have your wife tell her mom that just you and her are going on a vacation together with no one else.

Your wife’s in her thirties now; every trip doesn’t need to be a family vacation.

In fact, the entire purpose of getting your parents to watch your son was to allow the two of you to take a vacation together. That’s a pretty strong argument your wife can lay out to her mother and it shouldn’t be hard or remotely complicated for her mom to understand this.

It’s also better than you trying to avoid this situation by spending more money than you can afford on a cruise in the hopes of outpricing your family’s ability to spend.

What happens if no matter what you spend — it’s not like you’re going to keep upping the cost until you rent a yacht, her family knows roughly how much you can afford to spend — your in-law’s keep matching your spend? Then you end up spending way more than you can afford on a vacation and hating it.

The solution here is simple — your wife needs to declare vacation independence from her family. (At least on this trip).

“We’re getting older and our last friend is finally getting married. Love him, but let’s say he’s a little unique when it comes to his beliefs in a traditional southern city in the middle of the Bible Belt.

First thing on the wedding registry? Please donate to Planned Parenthood. 

Thoughts? Donate to the Trump campaign in his name? NRA?”

My first thought upon reading this question? This feels like a fiancee who is angry at his family’s political beliefs and wants to make everyone know what she believes.

I mean, do you know any straight guy who is that involved in the wedding registry?

I’m not even sure I’ve ever been on a wedding registry, including my own.


Who really cares? This is like screaming, “I ONLY LIKE TRUCKS, OTHER CARS SUCK!” if you were a big truck guy. Okay, cool, I don’t care dude. Nor does anyone else.

Plus, it’s just strange.

Have you ever been to a wedding and found yourself thinking during the ceremony, “I wonder what the bride and groom think about abortion?” (Or the second amendment or immigration policy, or anything else political for that matter.) I’ve never been to a wedding where I’ve thought about anything other than which hot bridesmaid has slept with the most men and how many people have the bride and groom slept with who are currently attending the wedding?

Why can’t people be normal like me?

Given their decision to interject politics into the wedding, however, I think you should definitely make a donation on behalf of the couple to Donald Trump’s reelection or, even funnier, to that foundation trying to build a wall at the border.

If they complain, just say with a straight face, “I thought based on the wedding registry that you guys were big border wall people, my bad.”

Maybe they will be furious at you for  the donation, but if that’s the case why do you want to be friends with them anyway?

It’s better to cut them off now than when they request donations to Elizabeth Warren’s presidential campaign in lieu of gifts for their one year old.

“My wife and I are happily married, and have 3 children. 

In the past my wife has always had a nice body, naturally thin and can eat whatever she wants while maintaining this figure. 

After the 3rd child, the baby weight has hung around and for the first time in her life my wife is carrying a little extra weight. 

Here’s where I need advice… She is upset about the extra weight and makes comments or complaints about it maybe 10x per day. Yet at the same time she will usually eat several desserts throughout the day. Coffee cake for breakfast, cookies at lunch, pie or ice cream before bed etc. We exercise together, but I have yet to bring up the diet because she gets defensive about it…

I want to help her lose the weight, but how do I approach the self sabotaging? What is going on here… Is it a denial of a new metabolism? Perhaps eating her feelings? What should I do?”

Your question, boiled down to its essence, is how do I tell my wife that I think she’s fat?

And the answer is, you pretty much can’t do this and stay alive (or married) if you’re a husband.

So what you do instead is announce you are fat and going on a diet and ask her if she’ll join you. (If you are totally ripped and have zero fat on your body then this doesn’t work, but if you’re a dad of three with a full-time job and you’re totally ripped you’re already having an affair with someone else so your marriage will be in a shambles soon anyway).

So you go on a diet with your wife and hope you both lose weight.

Then you can have a couples diet! It’s so fun to eat the same thing and both lose weight together! Yay! (Note: this is not true. All diets suck. But you have to pretend it’s fun to share this with her.)

More seriously, you should also have a conversation with your wife about whether there’s something motivating the eating more than just the eating. In other words, is the eating and the weight gain a symptom of something — post partum depression, potentially? — more substantial than just the weight gain? Good luck with that conversation too, by the way, it’s difficult to have, but also could be very important.

If it’s nothing more substantial than just eating too much, good luck with the diet.

Thanks for reading the anonymous mailbag.

As always, 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.