Anonymous Mailbag

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It’s Tuesday, which means I’m here to solve all the problems in the Outkick universe.

As always, the anonymous mailbag is only as good as the questions you guys send in so with that in mind, keep the questions rolling in to, anonymity guaranteed.

Okay, here we go:

“Prior to covid, I used to travel to my current city for work about once a month. After work, I would usually hit up the gym next to my hotel and, on one of my first trips, I met a girl there. We grabbed drinks the following night and eventually ended up hooking up back in my hotel room. We didn’t talk much via text or phone after that but going forward whenever I was in town we would end up hooking up.

The situation was a little odd as it was always at my hotel room and never her place and she would never want to grab drinks or dinner. I found this a little suspicious but I was in my early 20s and didn’t want to mess up an ideal no-strings attached situation so I just kept my thoughts to myself. When I moved to my new city I hit this girl up but she told me she had moved away and was engaged now so I figured that was the end of it. I actually discussed this situation with my girlfriend one time and she laughed about it and said something along the lines of “Guys are so dumb that girl totally was cheating on her boyfriend with you.”

Back to my dilemma now- so this morning I was waiting in my girlfriend’s kitchen for her to finish packing as I was going to drive her to the airport. I was looking at some wedding save the dates on her fridge and she came into the room and pointed out the one for her cousin’s wedding this summer. She mentioned the fact that they had started dating in high school years ago and had been together ever since. Something didn’t sit right with me after that and I became a little suspicious. After I dropped my girl off at the airport and got into work, I immediately began putting my social media stalking skills to work. I was able to find my girl’s cousin’s Facebook page and my suspicions were confirmed. I didn’t recognize her right away because she had put on some weight and changed her hair color but this was definitely the girl who I used to hook up with in my hotel room. Unfortunately, based off the timeline I now knew of the relationship, she and my girlfriend’s cousin were dating at the time.

My girlfriend will be out of town for the next week so I have a few days to figure out how to approach the situation but what do you think I should do? I don’t like having secrets in relationships so hiding this will not sit well with me. There’s also the fact that I will have to “meet” this girl when I go to the wedding later this year. I don’t see any way in which that fake intro won’t be noticeably awkward as hell. However, if I do say something I feel like this dooms my relationship with my girlfriend’s family. I mean I will forever be the guy who helped ruin an engagement/marriage even if it was unintentional. I could see how some people may never possibly get over that fact. My girlfriend originally found the story hilarious but, being she know has a very personal connection to it, I have no idea how she will respond.

What’s my play here?”

To me, you have two options: 1. never say anything at all. 2. tell your girlfriend the truth and let her make the decision about what to do. I think either option is fine, but option two is the only way you completely cleanse yourself of any future issues. The downside to option two is you then put everything on your girlfriend’s plate and put the moral conundrum in front of her.

I don’t know your girlfriend at all, but I tend to believe she would probably choose to stay quiet rather than (potentially) blow up her cousin’s wedding. (Her decision might be different if her cousin was the person being cheated on as opposed to doing the cheating.) But either way, once you tell her the truth, that’s her choice, not yours.

The other wild card here is you’re assuming this girl never confessed her cheating to her boyfriend. What if that’s not true and she confessed? And he’s gotten over it, primarily because she told him it was a totally random guy that he’ll never meet, and then, boom, suddenly he realizes you’ll be around, potentially, for the rest of his life. And now he knows that everyone else knows about it too. My point, you never know what two people discuss inside their relationship and parachuting in with what you believe to me a major revelation might not actually be a major revelation at all. Which is why my general advice is to stay out of other people’s relationships.

Now I don’t know you at all so maybe you’re the hottest guy who has ever lived and are therefore irresistible to all women, but I also don’t think it’s very likely that this girl has been completely faithful to her fiance and then banged a random guy she met at the gym at his hotel room. In other words, the kind of girl who bangs a stranger she met at a gym in his hotel room doesn’t feel like the kind of girl who is otherwise faithful in relationships. Not to distract from your otherworldly sex appeal, but that’s why my bet would be that she’s been banging many other guys.

(By the way, this is why my argument has always been that even if women won’t admit it, they feel better if you confess to cheating with a smoking hot woman. Now they’re not going to be happy, but it’s easier to claim you only cheated with a smoking hot woman. If you cheated with an ugly chick, it probably means you were banging everything that moved. And the same is true for men, if your girlfriend banged Brad Pitt you wouldn’t be happy, but you’d feel better than if she banged a random pizza delivery guy. General rule: the lower down the food chain the banging partner is, the more likely it is that the banging wasn’t just with that one person. Here in our scenario, this girl was probably banging a bunch of guys.)

So the safest thing to do is just come clean. Especially because your girlfriend previously said this girl was totally cheating on her boyfriend when you told her the story. So when you come clean you can let her know that she was 100% right. Again, I think the most likely outcome is that after thinking about this for a while, she chooses not to say anything at all.

But if you choose not to say anything, you first better hope your girlfriend doesn’t read the Outkick anonymous mailbag because this story is specific enough that if she does read the anonymous mailbag, you’re done for.

Secondly, you have a potential cover story in that the girl now looks quite a bit different than she did then. That is, you can claim you didn’t think it was the same girl if this ever goes public. But here’s where I think you might be being dishonest, even in the anonymous mailbag: how many guys really wouldn’t recognize a girl they hooked up with for a while, even if she put on some weight. Plus, did she lie about her name too? If so, wow, that’s the kind of dishonesty here that feels sociopathic. But that seems like a big detail to leave out.

Even if she didn’t tell you her last name, did she lie about her first name too? Wouldn’t most guys who see a picture of a girl with the same first name notice they’d hooked up her without having to engage in social media research? Because that would be one of my first questions for you if I was your girlfriend.

You need to clean your story up, buddy. You need to say you saw her picture on the fridge and immediately realized who she was. As is, this makes me think you were banging her while you were dating your current girlfriend. That is, both of you were cheating and that’s the real moral dilemma here, you’re trying to figure out if she’s going to confess to your girlfriend or not.

But maybe I’m reading too much into your email.

That’s why the safest option, if you truly want to be with your girlfriend going forward, is to come clean with her about all of this. Especially because if you did decide to come clean, I disagree that you would doom things going forward with your girlfriend. Based on the details you’re sharing, you didn’t do anything wrong. (This is assuming your email is honest.)

If it later comes out that you did have a relationship with this girl — and call me crazy, but I feel like this girl may not have that stable of a marriage — and you lied about that with your girlfriend, that’s when your relationship actually comes to a close.

So based on the details you provided, this is a tough call, but I’d tell your girlfriend about it.

“Sunday I took my dogs and two kids (9&12) up to the local high school where my dogs can run on the practice field and play. I noticed a flag football game going on at the soccer field and could hear a crowd. I also could hear players yelling at each other an the N word was said often.

I got over to the game and the stands were pretty packed. Made small talk with one of the guys and he said it was sophomores and juniors from the high school and they played these games for practice in the spring. Over the next twenty minutes I heard the N word a minimum of 100 times. Every other word it seemed like. The teams were 7 v 7 and all black except both QBs were white and one team had a Hispanic guy. It got to be a little much with “Fuc$ you N…” “Get out of here with that shit N….”

The black guys were the only ones who said it and they even called the white QBs the N word. Am I just getting old because I found it pretty offensive at the rate and way in which the word was being thrown around? I know Joe Rogan recently got blasted for saying it (albeit from years ago) but it seems like if society has a problem with one race using the word, shouldn’t we have a problem with all races? Or am I just out of touch on this?”

Our society’s speech codes are completely broken.

There is a difference between a racial slur and rap lyrics. It’s absurd that Asian, Hispanic or white kids could get kicked out of school for rapping along to a popular song on tik tok while black kids can scream racial slurs at other races during sporting events and have zero consequences.

But that’s where we are as a society right now.

It’s because we’ve completely lost the ability to use context to determine what’s appropriate and inappropriate.

Think of all the ways the f-word can be used. It can be an insult — “F-you!” a verb, “Let’s f-,” an adjective of praise “f’ing incredible,” or an adjective of derision, “f’ing awful.”

And all of us are smart enough to know the difference based on the context in which the f-word is used. That’s because words are all defined by the context in which they are used. They always have been and they always will be.

Having said that, I teach my kids not to use racial slurs in any context and more importantly not to treat anyone differently based on their identity. I suspect most adults do the same with their own kids. And I’d encourage you to use what you saw in the park as a teachable moment for your own young kids.

Taboo words have always been, and will always be, a part of American speech. Just witness the power of George Carlin’s comedy act in the 1970’s that took aim at FCC restrictions based on curse words. What’s unique now is the left wing most zealously polices what is and is not allowed to be said.

In my youth it was more likely to be right wingers trying to cancel musicians based on their word choice, now it’s the left wing.

Our left wing speech policing is a natural outgrowth of the two foundational tenets of the Democratic party: 1. identity politics and 2. cancel culture. I believe the Democrats are going to get destroyed in 2022 and in 2024 based on these two issues. Why is that going to happen? Because I believe increasing numbers of Hispanic, Asian and black voters are going to begin to vote for the Republican party because they also reject the identity politics and cancel culture of the Democratic party.

When the Democrats realize their identity politics and cancel culture policies are leading them to ruination, they will abandon them.

But first has to come the electoral destruction.

And I firmly believe it’s coming soon.

But in your situation, there’s no value in being the white guy who spends a substantial amount of time, energy or effort arguing about what words kids use in a high school football game. Because the kids aren’t going to get in trouble over this, you are.

There are many things I’m concerned about in America right now — teenage word choice hypocrisy doesn’t rank that highly for me.

“Sending from my official military email address as proof that I am who I say I am but would appreciate anonymity.

This really isn’t a question for the anonymous mailbag but more plea for help. I live on a military installation and my kids attend school on-base. As such, parents in my situation have virtually zero recourse or voice with any school board. The schools are run by DoDEA (the Department of Defense Education Activity). DoDEA is part of the DoD which reports and is directly controlled by the President.

Our kids are stuck wearing masks all day, even while outdoors at recess. School administrators are powerless to change that rule as it is established at DoDEA HQ. As schools around the country lift mask mandates in favor or parental choice, military families – those serving on the front lines – have no ability to effectuate school policy. Many fear speaking up for fear that it may impact our careers (I’m senior enough that I don’t really care but one voice doesn’t make for an effective movement!).

So, I guess if this really is a question, what can parents in this situation do? How can this issue be amplified? How can we get the same attention as parents (rightfully) admonishing school boards? Can you help?”

I’m including this in the anonymous mailbag to help drum up pressure on the absurdity of this rule continuing to exist for kids on military bases.

Thanks for your service and for your email.

Okay, I’m headed to Florida on Thursday for spring break — and then out to Vegas for the opening weekend of the NCAA Tourney — but in the meantime I need you guys to keep your anonymous mailbag questions coming.

As always, send them to

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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  1. – Hotel Trollop: I’m confused here, is the current gf’s cousin the dude or the chick?

    “I was able to find my girl’s cousin’s Facebook page and my suspicions were confirmed. I didn’t recognize her right away…”

    “Unfortunately, based off the timeline I now knew of the relationship, she and my girlfriend’s cousin were dating at the time.”

    Based off Clay’s response “Her decision might be different if her cousin was the person being cheated on as opposed to doing the cheating.” it sounds like the cousin is the chick but I read that assuming it was the dude being cheated on.

    • Idk what’s worse; you hooking up w/ her female cousin or you unknowingly ruining her male cousin’s potential marriage? If her cousin is the female she may resent you forever at no fault of your own but she would be less likely to blow the situation up. If the cousin is the dude it’s more favorable long-term but then she may be more inclined to blow the situation up and half her family will hate you.

      Also, agree w/ Clay. How are you gonna look at the photo and first name and not know it’s her? Unless you’re blacked out drunk on a one night stand it seemed implausible you would know and would need to hop on fb.

      • I agree it’s confusing whether the cousin is the guy or gal in the relationship, but I don’t think he said he saw her picture on the fridge. A lot of save-the-dates and invites don’t have any pics of the couple on them. I think he just saw the name and had to search to see if it really was her.

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