Anonymous Mailbag

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It’s Tuesday, and the anonymous mailbag is here to solve all your problems.

But before we do that, Michiganders, rejoice! Online sports gambling is going to be legal from your phones in a matter of days. And right now you can get signed up so you’re ready to place bets the first day it’s legal. Plus, you can get a free wager of $1k. The same free wager that everyone reading this in Tennessee, Indiana, Illinois, Iowa, West Virginia, Colorado, Pennsylvania and New Jersey can also get. So go get signed up today.

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

Okay, here we go:

“Dating in the midst of the pandemic has been weird. I’m in my mid 30s, and I recently began dating someone also in her mid 30s. Things are going well between us. The problem is that she’s a doctor who sees a lot of elderly patients and whenever we’re together she wears a mask or face shield… or both. She’s not scared of getting COVID but she is scared of being asymptomatic and passing it to an elderly patient who gets very sick and possibly dies. I feel that’s a totally understandable concern. Because of her concerns we haven’t been physical… at all. I mean not even a hug. How am I supposed to kiss her if she always wears a mask? What would you do in my shoes, King Solomon of the Internet?”

Well, it’s pretty clear you are willing to risk COVID infection to kiss her, but it seems like she may not be willing to do the same to risk kissing you.

Rather than dance around this issue, I’d just directly ask her. The advantage you have is you’re both in your mid 30s now. It’s not like this is your first adult relationship.

I’d go with something simple like this: “We’ve been dating now for (insert length of time), and I’d like to be able to kiss you. I understand that might make you nervous with your job, and I’m not asking you to make decisions that make you uncomfortable. But how long do you foresee us dating like this, without any physical contact?”

I think that’s a reasonable question and that you’re entitled to an answer to that question.

Is she not going to kiss you until there’s a vaccine? That seems crazy to me, but it may be her plan. And if that’s her plan, you deserve to know so you can make your own decisions about how much you value your relationship with her.

Again, you’re in your mid 30s. It’s not like you’re 22. Presumably you want to get married at some point. Are you both going to invest a year or more in a contactless relationship while you wait for a vaccine? That seems wild to me, but if both of you are okay with it, that’s a choice you can make together.

By the way, I have no idea what kind of sense of humor she has, but you could have a lot of fun with defining her acceptable intimacy standard as well. For instance, I have so many questions here. Let’s say, she’s opposed to kissing, but is she also opposed to heavy petting while wearing the masks? Can you get naked and roll around touching each other while wearing latex gloves and masks and face shields? Can you have sex while wearing masks and face shields? Can you get a hand job while she wears the face shield and the face mask? What if you drop your pants and she reaches out for a socially-distant hand job while you stand as far from her as possible? What if you wipe your penis down with Clorox wipes before she touches you? Can you have FaceTime sex entirely remotely? Can you watch her masturbate while standing in the corner and jerking off yourself in a gentlemanly and socially-distant manner? In other words, what sexual interaction can you negotiate here? I’d actually be fascinated to know.

In fact, please update us.

In the meantime, I just hope your serial killing COVID penis doesn’t kill her elderly patients.

“I am a student at a high school, and we have to wear masks everywhere we go every day. It is very strictly enforced, and there is even a 3 strike policy that if you’re caught violating it 3 times, you are forced to go online. But, the other day I saw my principal walking around, near people, with no mask of course. Once he realized people were taking notice, he tried to pull his shirt up over his nose. How am I supposed to respect and follow these rules when the person in change can’t even follow their own rules?”

First, you’re a kid at school, which means, unfortunately, you aren’t in a very powerful position. What you’re pointing out is hypocritical behavior by your principal. It’s entirely fair of you to ask how you’re supposed to respect and follow the rules when the leader of your own school, an adult who has implemented the rules for all of you, isn’t following them himself.

I’d email yourself the date and time you saw your principal without a mask and if, at some point, you are accused of violating the mask rule and face being sent home for a third strike, you can point out that you, like your principal, are imperfect and should deserve another chance.

Odds are your principal wasn’t intending to flout his own school’s rules. He probably just did what most people in this situation do. He forgot to grab his mask and then realized what he’d done when everyone started to take note of his behavior.

But, guess what, the foundational lesson of leadership, I believe, is that a leader shouldn’t ask his followers to do something he isn’t willing to do himself. A leader should follow his own rules more assiduously than everyone else.

What we’ve seen with many of these histrionic COVID rules is, deep down, our political leaders known many of the rules they are implementing are completely absurd, and they won’t follow them. That undermines trust in the leader because it shows how hypocritical his behavior is.

We’ve seen many politicians — the governors of California and New York, the mayor of Denver, the mayor of San Jose, the list goes on and on — publicly flouting their own directives. They want you to do things they themselves aren’t willing to do.

That kind of leadership is wildly hypocritical and destined to fail.

Here’s an easy example: just about every politician has their kids in private school. So their own children are receiving in-person instruction while they are shutting down public schools and making kids learn remotely. If you are insisting on behavior for other people’s kids that you aren’t willing to follow yourself, that’s the very definition of hypocrisy.

Again, as a kid in school, I don’t think you have much power here. But I’d keep this incident in my back pocket if I were you, potentially as a way to argue that the draconian punishment of being sent home for remote learning shouldn’t apply after just three strikes since the principal himself has at least one strike too.

I can’t imagine how frustrating it is to be a kid at school right now and have to follow the COVID rules of so many hypocritical adults. Good luck trying to do so.

“My girlfriend is white, and I can tell my Indian mom does not want me dating a white girl. I was wondering how to approach this. It has been a year and a half almost now, and I want and know this relationship will work out, but I want to be able for this to be a non-stressful issue.”

Two of my college roommates were Indian, so I’m familiar with the pressure that minorities of relatively recent American immigration status can feel from their parents to pick someone from their own racial background to marry.

So let me unpack this a little bit.

I don’t know your mom, but like most immigrants, she probably loves many of the things about her culture that she experienced in her youth. But not everything, which is why she immigrated in the first place. Now she feels she’s able to balance the best of India and America. And while I’m sure she also loves America and loves the opportunity the country provides to you — that’s why she came here — like most immigrant parents, and parents in general, she doesn’t love everything about America.

And she doesn’t want you — and her grandchildren — to turn into the things she doesn’t love about America.

So she’d like for you to represent the best of India and the best of America. How does that happen most efficiently in her mind? By you picking someone from the same background so you can continue to instill the values she embraces — religion, culture, life — and not leave her with totally Americanized kids who have no interest in her life or values.

She doesn’t want, in other words, lazy American grandchildren.

It’s not about the wife, it’s about the connection the Indian wife represents to the things about India she loves.

The best way for you to address her concerns is by pledging that you aren’t going to abandon your culture, no matter whom you marry. That’s what she wants to hear. Will it alleviate the tension and issues? Doubtful. But that, I believe, is the root cause of many parent and daughter-in-law or son-in-law conflicts, regardless of racial background. It’s a fear that the new partner won’t understand or cherish the same things that the parents do.

Honestly, when you think about it from her perspective, every parent or grandparent, deep down, would like to leave their offspring in better shape than they were, but without repudiating all the values that they also embraced as children.

I’ll give you an example in my own life. I was raised very middle class. Literally smack dab in the center of middle class. I went to fairly mediocre public schools until I got to seventh grade, when I really got into a great school. But I think my background was beneficial to me. Because it meant that I had to learn how to get along with everyone, regardless of their background, rich, poor, white, black. I grew up with a fairly representative cross-section of Nashville kids.

And I think that’s served me well in my life.

Being squarely in the middle of middle class also gives you a window into the upper class, where you’d like to end up, but you also see the lower class, where you hope to not end up. When you aren’t raised wealthy and aspire to financial success, you learn you have to work your ass off to get there. You aren’t being handed any measure of success. So how do you instill a deep work ethic in kids that don’t really want for anything of a financial nature?

I worry about that with my own kids.

In the grand scheme of things, it’s a small worry, but it’s something that nags at me quite a bit. How do I make them realize what the real world is like, when their reality is a gilded existence of the real world? The truth is, I’d like them to have some rough experiences in mediocre to bad public schools to toughen them up some, but that’s not going to happen for them the same way it did for me.

Again I don’t know her, but I think I can probably understand your mom’s perspective. She’s worried that your kids are going to lose track of their past and her culture. She sees an Indian wife as a pathway to instilling similar values in her grandchildren. I think what you need to make clear to her is that you are that pathway. That you won’t allow your own children, regardless of whom you marry, to forget where you came from or to forget the importance of your Indian culture.

And that ultimately raises a really fascinating dichotomy: we often want our children — and ourselves — to ascend to heights far beyond where we began, while simultaneously remaining the exact same people that we were long ago. That, of course, is a bit of a fantasy, but it represents, at least I think, the dueling dynamics of the American dream. We want educational, financial, and cultural progress, but simultaneously, we want to retain many of the things we had before we achieved that success. We want the future to be a better version of our past, not a complete rejection of it.

And that, no matter who you are or where you come from, is virtually impossible to accomplish.

As Thomas Wolfe said so long ago, you can’t go home again.

But we never stop trying.

“When should kids move out of their parents’ house? I think it should be as early as possible, but is it hypocritical for me to think that when I graduate from college this spring at 22 years old, I plan to still be living with my parents for free?”

As a general rule, I agree with you.

Kids should move out of their parents’ house as soon as they can financially afford to do so.

I think that’s an important marker of adulthood.

But failing to do so, if you don’t have the resources to do so, doesn’t make you a hypocrite. To me, hypocrisy is a choice you make that puts you in direct opposition to what you’ve argued for or against. Telling everyone to wear a mask in public and then failing to do so yourself is hypocrisy. Intending to wear your mask and forgetting to do so every now and then isn’t hypocrisy.

If you argued that every kid should move out of their parents’ house as soon as possible, had the resources to do so yourself, and yet failed to do so until you were 32, that would be hypocrisy. What you’re describing is something very different.

Believing in something you aren’t yet able to do isn’t hypocrisy. It’s ambition, which is a good thing.

If you believe that every person should buy his or her own home by 30 years old, it isn’t hypocrisy if you fail to attain that goal. It’s an ambitious target that you may or may not meet. But it’s not hypocrisy to fail to live up to a goal.

You’re mixing up ambition and hypocrisy.

And, by the way, it’s not hypocrisy to decide to save up money and live with your parents either. Sometimes you get new facts, which can cause you to reexamine your previous beliefs. Maybe you believe that people should move out of their parents’ house, but you also don’t believe it makes sense to pay rent and just give that money away. So maybe your goal is to save up money while living with your parents so that you can buy your own place.

Having goals is a great thing, but sticking to those goals, no matter what the circumstances are, isn’t always the best idea. Sometimes you need to modify your beliefs in order to attain a greater result. Living with your parents might allow you to buy a home sooner rather than later. Since having your own place is probably the ultimate goal, it wouldn’t make sense to sacrifice your ultimate goal — home ownership — in favor of a lesser goal, renting your own place.

I believe the best mindset is having a goal but also recognizing there is more than one way to get to that goal. You need to be a flexible and dynamic thinker, as opposed to a dogmatic thinker.

There are multiple pathways to success, not just one.

“I have been with my company for over 7 yrs now. In the last 3 years, I’ve received a total of $1.50 per hour in total raises. My boss says he is giving me a 2% raise every year which is roughly 50 cents every year on the hour.

I make $24.75 an hour, and for some folks, that’s great pay. But for me (no wife/ single/ just standard bills), I am very frustrated by the lack of raises coming my way. And he does this for every employee. (2% across the board). The only reason I stay is I live 5 miles from the shop, I drive a company car when on the clock, I have a ton of freedom and I can pretty much take off when I want or work as much overtime as I want.

But I’m 44 and don’t wanna work the 55+ weeks anymore of the hard labor.

I wanna quit, and I just get my real estate license. (All I have to do is pass the test) but with jumping into real estate, I would need at least 6 months of savings to start. Looking for any advice at all would greatly be appreciated.”

By my math you are making roughly $50k a year on a forty hour work week. Assuming you work a decent amount of overtime, it sounds like you could make $60k or so pretty easily. I don’t know what city or state you live in, but as a single guy with no wife or kids, that’s a pretty decent lifestyle.

Now you’re thinking about becoming a real estate agent and asking me for advice there.

But your email to me feels a bit contradictory: you’re complaining about pay, but also saying you don’t really want to keep doing your job.

So do you want a new job or do you want to make more money at your current job? Because those are two different situations.

If you want more money at your current job, you need to make the case to your boss that you’re worth more money than he’s paying you. That requires you to think like an owner, as opposed to an employee.

So the first question you need to answer is this: how much money is he making off your labor? Do you have any idea? If you don’t, then it makes arguing for more pay hard to do. So you need to figure out what your labor is worth. One way to do that is by getting an offer from someone in a competing company. In fact, that’s often how employees find out the worth of their labor. Can you do that? If not, another way is to find out what your work is billed out at and how much profit there is built in there.

Clearly, the owner of the company is making money on your labor because he’s giving you a salary increase every year, but how long could that continue and he still be making money on your labor? You need to figure that out.

But the bigger question is this: do you want a new job, or do you want to be paid better at your existing job?

Second, I’m not an expert on real estate, but what you’re considering is going from a job where you are directly compensated by the hour — that is, you’re paid as an employee by a boss — to one where you effectively become an independent contractor and are paid a commission based on sales. That’s a totally different job.

If you think you are underpaid as an employee, what makes you think you will be more highly paid as a real estate agent? It seems to me that you would have no idea what you might make there. And if you’re worried about working too much, it seems to me that most highly-paid real estate agents who are successful work their asses off.

You’re smart to recognize you’d need six months of savings to make this move, but what makes you think you’d be good at this job and what makes you believe you’d make more money there? In other words, why that job instead of the one you have?

So you really have two different questions at play here that you need to resolve before you can make a good decision. And what it really boils down to is this: what’s the salary at your current job that would make you happy to stay there, and are you more likely to make that salary as a real estate agent or not?

Good luck answering these questions.

Until you can answer them well, it’s hard to make a reasonable and rational choice when it comes to your job.

As always, thanks for reading OutKick’s anonymous mailbag. Send your questions to, anonymity guaranteed.

Written by Clay Travis

Clay Travis is the founder of the fastest growing national multimedia platform, OutKick, that produces and distributes engaging content across sports and pop culture to millions of fans across the country. OutKick was created by Travis in 2011 and sold to the Fox Corporation in 2021.

One of the most electrifying and outspoken personalities in the industry, Travis hosts OutKick The Show where he provides his unfiltered opinion on the most compelling headlines throughout sports, culture, and politics. He also makes regular appearances on FOX News Media as a contributor providing analysis on a variety of subjects ranging from sports news to the cultural landscape. Throughout the college football season, Travis is on Big Noon Kickoff for Fox Sports breaking down the game and the latest storylines.

Additionally, Travis serves as a co-host of The Clay Travis and Buck Sexton Show, a three-hour conservative radio talk program syndicated across Premiere Networks radio stations nationwide.

Previously, he launched OutKick The Coverage on Fox Sports Radio that included interviews and listener interactions and was on Fox Sports Bet for four years. Additionally, Travis started an iHeartRadio Original Podcast called Wins & Losses that featured in-depth conversations with the biggest names in sports.

Travis is a graduate of George Washington University as well as Vanderbilt Law School. Based in Nashville, he is the author of Dixieland Delight, On Rocky Top, and Republicans Buy Sneakers Too.


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  1. I think 18 is the move out of the house age. You can stay at the house when you’re home from college on breaks but then fully out at 22 when you graduate. Or out at 18 if you choose not to go to college.

  2. it will become easier to date going forward. let me explain with a hypothetical.

    -girl meets guy and she is wearing a mask.

    -guy asks if she is sick? Or does she have bad teeth/breath? or a mustache?

    -she looks confused/annoyed/suprised (her eyes do). she says something unintelligible through the mask.

    -man puts on his mask and leaves the bar/church/strip club

  3. The comment about the Indian young man with the white girlfriend was interesting. One huge factor that you overlooked, or barely touched upon, is religion. Indians are overwhelmingly Hindu and/or Muslim. For an Indian mother looking to keep her religious identity/beliefs alive, that would prove a huge barrier to marrying an American, who would most likely be Christian and/or secular. I believe the religious angle is the biggest hang-up that this Indian mother has in whom her son is dating, especially if it is about to turn serious.

  4. My oldest moved out for two years to live on his own his own way. Bombed. Asked to move back to save up money to go to trade school. We let him do it. After 6 months, zero money saved and doing less around the house then he did in high school we booted him into the deep end. He’s had it rough but is surviving on his own this time around. Bonus point is he seems serious about finishing school now too on his own dime.

    For the person who has been sold on the idea that being in real estate is easy money with less work please just do an internship at a real estate company first before you give up your other job. To make money in that industry you have to work far more than 40 hours a week and be really good at kissing butt to those who don’t mind wasting your weekends looking at properties they have no intention of buying. But you do it anyway for the one person who will buy and make you 10% what you need to survive that month.

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