Anonymous Mailbag

Rejoice, it’s Tuesday!

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

If you’re reading the anonymous mailbag and worried about the coronavirus, be at ease: Memphis has got us taken care of. Ain’t no way the virus is getting through these defense mechanisms.

(I can’t stop watching the dad spraying his kid down with disinfectant, likely taking ten years off his life in the process, and the woman in the hand-made coronavirus protective suit. This is top shelf local news entertainment.)

And, remember, whatever happens, if the world is ending make sure you have toilet paper.

Okay, here we go:

“I cannot ask anyone else this, as I have been humiliated by it all. 

One Friday night I came home after work and my wife was waiting for me, but the kids — ages 10 and 11 — were at my parents house, and she dropped this bomb on me.  She wanted a divorce after 13 years of marriage because she was back together with her ex.  I was shocked. We got married at age 22 and have been together since we were 19, and I had no idea who this “ex” was. 

She told me that he was the true love of her life, that she settled for me, and never felt in love with me, and once she saw him again she knew she loved him and not me. As you might imagine, I was a mess for weeks.

Then all of a sudden, I was having a quiet fling with one of her best college friends, who was divorced last year. I don’t think she has an emotional attachment to me, and I certainly do not to her. She looks good and we have a friends with benefits situation, that’s it.  She has a kid that she is devoted to, which I of course respect. She doesn’t want anything more than companionship in the same way I want it, and she wants to keep it on the down low. 

To the shock of no one who knows men, the guy my soon to be ex-wife left me for enjoyed banging someone else’s wife and then lost interest in her when she expected him to stick around and be involved in a relationship. 

I have stayed at my house 5 or so nights a week since this went down, while keeping a nice apartment nearby. I of course do this for the kids, who are everything to me. A few weeks ago, my soon to be ex-wife asked me if I wanted to go to counseling and save our marriage and, my favorite part, “fall in love all over again.” That was funny because she told me she never really loved me to begin with. Anyway, my plan has been to keep right on with what I have been doing. Stay at my house a lot of nights to be around my kids, and go spend time with this other woman (and other women) when I want and need to. 

I do not want to be a weekend Dad, and I know that being away from their mother 50% of the time will not be good for them, but at the same time how can I try to save my marriage when my soon to be ex-wife told me she never loved me and decided she’d rather be with someone else?  Plus, I also know she wants to keep the nice, cozy stay-at-home Mom life she has had for years, and would likely play the role of “falling in love with me all over again” just to keep it.  Lucky for her, my pain and anger hasn’t made me lose sight of what my children want and need, and that’s her involved in every aspect of their lives, volunteering at school, activities, etc.  Making her go back to work right now would only be out of spite and would only hurt our kids, so I haven’t done it and frankly do not intend to force her to go back to work anytime soon no matter what happens.  Tell me how I can keep this going for about 5-7 years.”

Let’s start here: your kids are ten and eleven years old now.

While your arrangement works now at some point, probably in a couple of years at most, they’re going to realize that dad has an apartment and disappears for a few nights a week, right? I suppose you could lie to them about being out of town for work for another year or two, but don’t you think you’d eventually run into them around town as they become teenagers? And eventually they’ll find out that you’re hanging out with other women because even if your kids don’t see you around town their friends will. Putting it pretty simply, the older your kids get the less you’ll be able to set up a fake relationship with their mom and have them believe it’s real.


I mean that’s not one bomb she dropped on you that’s a triple atomic bomb she dropped on you simultaneously. What’s more, it was a premeditated triple bombshell. She sent the kids away so she could drop triple atomic bombs on you and not have them there to hear you lose your mind.

I mean, that is just such a cold blooded, premeditated I don’t care about you at all move. She’d probably been planning this for months. Then it turns out her high school boyfriend of TWENTY YEARS AGO doesn’t actually have any interest in being the love of her life so she tries to win you back by suggesting counseling so you could “fall in love all over again.”

I honestly don’t know how your immediate response wasn’t, “Don’t you mean fall in love for the first time?”

That’s a mic drop, walk out and never speak to each other again without lawyers present moment if I’ve ever seen one.

Frankly, I’d bet I’m like most people reading this mailbag right now when I say your behavior has been infinitely better than 99% of men (or women) would have behaved in a similar situation. You haven’t done anything wrong at all and you’ve tried to be the adult in this relationship. (Even keeping the side fling quiet isn’t a bad move on your part since it’s perfectly reasonable given the triple atomic bombs dropped on you that you’d want to find someone who found you desirable.)

The real question you have to decide here is how long can you keep this charade going? And how long until your kids find out about the charade? Because once they find out that mom and dad’s marriage is essentially a sham, what are you staying married for? I’d want out and I’d want out now.

Honestly, the fact you aren’t making your wife go get a job makes you a saint.

The fact you can put the kids first here and not seek revenge for her behavior is incredibly forgiving and generous of you. Because I think most men, or women, in this situation wouldn’t have been anywhere near this accommodating of what sounds like a pretty awful spouse.

It’s rare I suggest a divorce, but I think you should get divorced.

Your wife said she never loved you and attempted to leave you for another man. Once he rejected her, she came crawling back to you. You can still be a good dad without being married to this woman. Put simply, you can’t trust her.

I’m not thrilled about her having primary custody of your kids either, but at least they aren’t incredibly young. Seek as much custody of them as you can manage and make a good home for them when they are with you. Tell them you’ll explain why you got a divorce when they are older, but for now just make it clear you love your kids more than anything.

The fact that you’ve been willing to put up with your spouse so far is testament to that, if nothing else.

“My lifelong buddy and I have named you non-binding arbitrator of our dispute. I am in my mid-30’s. Over a year ago now, I was in an almost sexless marriage and as miserable over it as you would expect. I thought for sure my wife was cheating on me and I did some really humiliating stuff trying to catch her in the act, but it turned out to be the simplest answer. She lost interest in sex and that was that. 

Because of my kids, I didn’t want to leave her, and I thought she would get past it. In the meantime, I worked at a downtown office for years. About 3 years ago, my old dirtbag boss hired this smoking hot 20 year old single mother who really wasn’t qualified for the job, but hired her anyway and told me straight out it was because she was hot. 

I was pissed at the time because I had a lot of work that the assistants needed to do and needed to be qualified for. Turns out being a single mother was a great motivator for her to learn and she became a great assistant. And yeah, as you would expect, the more I went without sex at home the more I thought about her, and we got along great at work and talked a lot about everything.

I decided to leave my office and open up my own office, and would have brought her with me but I could not because I couldn’t have her 5-10 feet from me all day, every day. At my going away happy hour, I had this idea that I was going to seal the deal with her, and even got a hotel room right by the bar. However, I chickened out making a move, and instead rubbed one out to her that night. 

We did text and talk a few times after I left. Two months later, I was doing great on my own and put the word out I was hiring another assistant. A few days after that, I got a call from her at around 5:15 asking if she could stop by on the way home. Right away I was thinking of the excuses I was going to give her why I was not going to hire her because there was no way I could have her around me all day every day because of how much I wanted her. So she came to see me and we had some small talk, and then she told me about the financial issues she was having and how she was going to wind up getting kicked out of her apartment and losing her car. I knew she was struggling as a single mother with a loser ex who didn’t pay child support (but was actually a great father other than that, go figure). As she was telling me this I was thinking I could give her extra work on the side, nights and weekends when I wasn’t there, and she would be perfect for what I needed done. 

She then started telling me about her friend who could get her a job stripping and how she could make extra money there. Then she hit me with it. “I’ll have sex with you as many times in as many ways as you want if you help me get out of this situation.” 

As you could imagine, I was ready to write the check and jump her on the spot, but I instead asked “why me?” She said “I know you have the money, I know you are hot for me, and you know I am not trying to trap you since you know I know you had a vasectomy. And I do like you as I think you figured out by now.”  

I told her I would make the deal if she also agreed to spend a weekend with me in Vegas and go with me on a business trip I had planned for San Diego. I knew she had never been to Vegas and had never been to California in her life. You could tell from her face she was thrilled with this deal. Since then, I have been basically her Sugar Daddy for the past year, and while her financial stress is gone, I think I am getting the better end of the deal as my needs are being taken care of often and quite nicely, and then some.

I was in Vegas with my old college buddies a few weekends ago and I cut out early for the first time ever, because I was flying her in for 2 days of fun. My lifelong friend smelled something was up and I wound up telling him everything. It has caused problems with our friendship. Not because he thinks I should be faithful to my wife like you’d think, but because he thinks I am promoting the exploitation of women and even sex trafficking because he says I am taking advantage of her desperation to take care of her son. I think he is being overdramatic and ridiculous, because I see it as two consenting adults having both their needs taken care of, and both benefiting from our deal.  Isn’t that what a good deal is supposed to entail? Hell, I let her son and his Dad use my family’s fishing cabin for father-son weekends more than once because she asked me to let them. I am not forcing anything on her, and she has never heard the word “no” from me, not once.

So, Clay, tell me, who is closer to being right. I agreed to you being non-binding arbitrator because I am going to keep this going until she replaces me with a younger and hotter guy she falls in love with, and at this point I don’t give a damn if my wife finds out, because she has to realize that having sex with me only twice in all of 2019 is not something that is going to to keep me loyal. Verdict?”

Okay, before we get to the morality and the dispute with your buddy, let’s get to the legality of your arrangement. You should totally, 100% separate her employment from the sex the two of you are having. That is, it’s a bad idea to sleep with your subordinate at work, period. But you especially can’t be paying her to sleep with you while she also does legitimate work for your business. You really ought to just be her sugar daddy and keep your business completely unencumbered from the relationship you have with her. Even as cool as you think she may be, this is a complete disaster in the event she files a lawsuit.

That’s the first point here.

Now let’s get to the morality.

You essentially have a sexless marriage. As a result you don’t feel guilty about sleeping with this other woman. So here’s the first question: how would your wife react if she knew about this relationship? Because let’s be honest, if you are traveling with your side chick people are going to start to talk. I know, it’s Las Vegas and San Diego, which I’m guessing are substantial distances from your home, but people from your hometown travel there. And they certainly get on airplane flights to go there. So the likelihood of your being able to keep this relationship a secret is fairly low. Especially since you said you’re letting your side chick’s baby daddy and her son use your family’s fishing cabin for vacations. And especially since you can’t avoid telling your friends about your relationship either.

Plus, where are you sleeping together? Are you getting hotel rooms? Do you have an apartment? Are you banging in the office after hours? Are you using her place? There are just a ton of major entanglements that could come into play here. Furthermore, while your wife may be fine not being concerned with your sex life — clearly she’s totally uninterested if she’s only sleeping with you twice in a year — but is she okay if your sex life suddenly blows up in a public way and it embarrasses her?

It’s one thing to be in a don’t ask, don’t tell marital relationship, but what happens when everyone knows — or she becomes convinced everyone knows — about your sleeping around? This is akin to the women who are married to philandering politicians for decades and then suddenly decide to leave them once the affairs go public. It’s not the affairs that bothered her, it’s the affairs going public and humiliating her that led to the divorce.

So you need to consider this potential outcome.

Leaving aside the job entanglement and the marriage angle, to focus on the actual dispute with your buddy, I see nothing wrong with the arrangement here. You’re both fully consenting adults. She was considering getting another job — as a stripper, no less — to take care of her family and instead she’s sleeping with you. If anything, it’s better for her family and for her to be in this kind of relationship than it is to work as a stripper. You’re not a danger to her — as she noted — and presumably she’s not having to work the late night hours of a stripper. In exchange for sleeping with you, you give her money, which seems like a fair and bargained for exchange.

She gives you labor — the sex — and you pay for her services. (For the record, I think prostitution should be legal. I don’t understand why this woman should be able to sell her clerking skills, but not her sex skills. So long as consenting adults are involved here, I don’t see how society is being harmed.)

If she’s a consenting adult happy with her decisions and you’re a consenting adult happy with your decisions, I see absolutely nothing wrong with your private relationship. Your buddy is out of his mind to compare this to exploiting women or human trafficking.

You, however, are out of your mind for telling your buddy about this relationship because that makes it infinitely more likely that others will find out about it, potentially including your wife. Any divorce attorney she ever contacted would be ecstatic to hear that not only were you cheating on your wife, but you were flying your side chick across the country to accompany you on business trips. What’s more, as stated above, he might even be able to argue that you were employing your side chick in an effort to disguise the relationship.

You’d get crushed in the resulting divorce and she’d also make you out to be the bad guy for anyone who asked why the divorce happened. Sure, you could argue the only reason you started sleeping with this other woman was because your wife wouldn’t sleep with you, but that’s not nearly as sexy of a story as wife leaves husband because he was banging his secretary and she caught him.

You’d be the bad guy here.

And there’s no way your young kids are understanding any excuse you could make about your sexual relationship being broken. You’d just have to wear the scarlet letter everywhere you went and own the blame for your marriage ending.

Ultimately, I think you are being way too public with what should be a very discreet relationship. You’ve got a side chick because your wife won’t sleep with you. Plenty of people understand how that can happen. But you can’t keep living with her in as public of a fashion as you are right now. And you definitely can’t employ her on the books. if she’s on your company’s payroll for any work at all, you need to stop that immediately and pay her directly out of your own pocket.

(By the way, for the women reading this, I definitely believe that most men end up with side chicks because their wives don’t sleep with them enough. Maybe I’m wrong, but I don’t think there’s that many men with side chicks who have wives sleeping with them four or five times a week. So if this is your worst nightmare — and for many women it is — then bang your husbands more).

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.