Anonymous Mailbag

It’s Tuesday and time for the anonymous mailbag to solve all of your life’s problems.

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

Also, as we get ready for the holidays, many of you will be traveling to different states for Christmas. If you’re going to be in Tennessee, Michigan, Virginia, Indiana, Illinois, Iowa, West Virginia, Colorado, Pennsylvania or New Jersey, or already live, work, or travel in these states, go sign up for sports gambling today. You can get up to $1000 with zero risk on your first wager. So go sign up today. 

Okay, here we go with the anonymous mailbag:

“My son is about a year away from driving. Soon, he’ll have to be added to our car insurance. As you probably know, males under the age of 25 pay the highest rates for car insurance each year (even if they aren’t listed as a primary driver of a vehicle). 

While teenage girls also pay relatively high rates, it’s typically 100s (or even 1000s) of dollars per year less than male teenagers. 

So this got me thinking: what if I declare my son as a transgender when I have him added to our policy? I could even have him get female on his driver’s license if the insurance would require that. He could of course then transition back to a male when he hits age 25. 

My son thinks this is a hilarious idea, and would totally go along with it. My wife is horrified. I’m pretty sure there’s nothing stopping me from doing this, and I don’t think it is illegal. It’s not exactly like the DMV or insurance companies require a doctor’s note to change your gender. 

What’s to stop thousands of Americans from doing this in mass for their teenage sons when they go on their car insurance?”

This is an absolutely hysterical idea.

As a preliminary, I have no idea what the law is here, so I’m not advocating for this in any way, but assuming you’re correct and there is nothing illegal about this, I love the idea of your family saving (potentially) thousands of dollars in car insurance by your son identifying as female on his driver’s license for the next decade or so.

This also makes me wonder if different car insurance rates are eventually going to get attacked by the woke police. If we’re all equal, why should some of us have to pay more for the exact same product? Shouldn’t everyone pay the same rate for insurance, regardless of their gender? Why should this insurance discrimination be allowed to stand?

More seriously, I wonder about several things here. Among them, does changing the gender on your driver’s license create health issues in the event of the need for emergency medical care? Despite what some would argue, biological differences between the sexes are very real. So if, for instance, your son was in an accident and he had to be rushed to the hospital, would they give him different medications if he’s listed as a woman on his driver’s license as opposed to a man? I have no idea because I’ve never worked in a hospital or studied emergency treatments, but I could see that as a potential issue.

Plus, what about when your son travels, for instance, and takes an airplane flight? Do TSA agents or airlines match sex and gender characteristics to verify identity? Do your passport and driver’s license genders have to match in the event of overseas travel? I have no idea, but that’s another potential pratfall here that come to mind.

Finally, how would this play out if your son had an accident and there was a lawsuit based on his car insurance? Would the insurance agency be able to accuse your son of falsifying his gender to invalidate coverage? Can an insurance agency even make these arguments in our current environment where it’s considered offensive to question anyone’s gender?

I’m just trying to think through some of the dangers.

The idea itself, however, is tremendous.

I’d love to know how this plays out.

“My coworker has what I think is an insane stance on their kids and Santa. He told his kindergartener the truth about Santa because the kid asked and he ‘doesn’t like lying to his kids.’ To me, lying to your kids is a big parenting tool to stay sane, from big things like this, to small things like ‘the ice cream store is closed.’ He now has two kids under 8 that know the truth and the rest of the office holds their breath this time of year when his kids are around ours.”

This is a tough call for all the parents out there — you don’t want your kid to be the youngest who knows Santa isn’t real, but you also don’t want your kid to be the oldest who still thinks Santa is real.

You want them to be right in the middle.

When it comes to always telling the truth to your kids, I think you have to use your common sense here. If your five-year-old asks where babies come from, does your coworker explain sex to them? Or does he just make up a story? My bet is, he just makes up a story. But maybe I’m wrong, maybe he takes them through the entire sexual process. If so, that seems crazy to me.


Because young kids don’t need to be told the entire truth about everything. They have plenty of time to age and understand more complex issues. Magical thinking around Santa Claus isn’t destroying any kids. Put it this way. Do you know any kids that grew up and deeply resent their parents lying about Santa to them? I haven’t met one in my entire life. Chances are you haven’t either. So the idea that your kids are going to somehow resent you in adulthood over Santa lies just isn’t true.

There are plenty of things parents can screw up. Lying about Santa isn’t one of them.

As a general parenting rule, I think you turn your kid’s Santa question back on them. Follow up their question by probing why they think Santa isn’t real and trying to gauge whether they want to believe Santa is still real or whether they don’t want to believe he’s real. That allows you to let them answer their own questions, but it also allows you to gauge the intensity of their interest.

“It’s not for me to tell you whether Santa is real because Santa doesn’t come for adults. He comes for kids, which is why it’s for you to decide,” is a pretty good answer.

For me, we have multiple kids — ages 12, 10, and 6. The 12-year-old knows Santa isn’t real. So now he gets to help put out presents on Christmas Eve, which makes him feel like an adult.

But I also had him swear that he wouldn’t ruin Christmas for his younger brothers. And so far, he’s kept his word. In fact, I think he enjoys seeing the excitement from his six-year-old brother.

My ten-year-old doesn’t really believe in Santa, but he doesn’t want to risk not believing. Which is where many kids are around his age.

Just like I’d hate for my oldest son to spoil it for his brothers, I’d hate for my kid to be the one to spoil kindergarten or first grade Santa dreams for kids. So I think that’s way too early to have the Santa discussion with your kids.

Every kid is different, but I think around the age of ten is when it’s time to let the kids know about Santa — and the damn elf on a shelf too — if you haven’t already done it.

But I just fail to see how kids believing in the magic of Santa is somehow going to harm them.

Again, as a general guide, you don’t want your kid to be the youngest or the oldest still believing in Santa. As long as they’re somewhere in between, I think you’re fine.

Final thought: I told my younger sister, who is two years younger than me, that our mom and dad were Santa Claus.

Her immediate response, “Mom and Dad are Santa Clause for everyone?!”

So I probably told her way too young.

“My husband and I have a great sex life. We’re always looking at ways to spice things up. Recently I asked him what are some of the things he finds really kinky and freaky. He told me he’s always thought the fantasy of a mother/daughter or sisters as a major turn on. I had an ex in college who thought similarly. Is that a common thing for men? And what makes them turned on by it?”

First, this can be a dangerous question. Because what happens if your husband had said, “I’m so glad you asked. I’ve been waiting for this moment for a long time. I’ve always dreamed of you pooping on me.”

Then next thing you know you’re buck naked some night trying to poop on your husband.

And that’s probably not something you’re into. Unless, it is, and then, man, you two were made for each other.

I thought I knew what guys liked, and then I go on PornHub and see what’s trending every day and I feel like the most boring dude on the planet.

I’m into your standard, good-looking-women-having-sex videos.

I don’t need a ton of spice on top of that.

But evidently I’m in the minority here.

Because the amount of step-mom, step-daughter and step-sister porn that is always trending is OFF THE CHARTS.

I mean, step-mom, step-daughter and step-sister porn is the Alabama of the porn universe, always up top no matter what happens everywhere else.

And I just don’t get it at all.

Maybe it’s because my parents never got divorced, maybe it’s because all of you out there with divorced parents really are super screwed up emotionally and you’re all huge perverts, but I just don’t get it.

But if I had to guess on why your husband is attracted to this, I’d think maybe part of your husband’s attraction here is the taboo nature of the sex. Sleeping with sisters or your wife and her mom is super transgressive and perhaps the societal transgression is what drives the interest to a large degree?

Also, I have to ask, are your sisters and your mom super hot?

Because that may factor in too.

I doubt many men find the idea of sleeping with sisters to be hot if the sister isn’t hot too.

As for the popularity of step-family porn, I’ve thought about this quite a bit. I think it’s probably the proximity of the opposite sex which aids in the fantasy here. In other words, sleeping with your step-sister seems both transgressive and also possible. Plus, it’s frequently connected to your teenage years, when your fantasies are most pronounced.

I’ve never been a teenager in a house where suddenly a smoking hot step-sister or step-mom moves in, but I’d imagine that proximity makes it just possible enough to believe that sex might happen. But it’s also transgressive enough that you rarely speak about it unless you’re logging on to PornHub.

Because the data doesn’t lie: tons of men love these videos.

“Clay, question here about developing and strengthening relationships as an adult.

37 years old. Married. 4 kids. Ages 10-1. So life is busy.

I know that it’s unique, but I have a fantastic group of friends. Most of them are friends from Elementary School, and then a few more who joined around high school years. We’re all busy with families and multiple kids, but still do 1-2 trips together, centered around fantasy football, and get together often throughout the year for different events.

My problem is that I don’t have a great relationship with my brothers. It’s not toxic, it’s just not there. I see them once a month at family dinner, and don’t really have meaningful conversations there either.

My question is, at 37 years of age and with a family of my own, do I try to fix, and improve the relationship with my brothers, or simply lean into the relationship with my friends?”

I think the toughest thing about the stage of life you’re in right now — and the one I’m in too — is the lack of time. Once you have multiple kids, a wife (or husband), and a job, there’s very little time for social life in general.

Before you have kids, from about the age of 14 to when you have kids, you have a ton of time to spend on your friendships. That’s why so many of these friendships are so deep and lasting. And I suspect that once your kids leave the house and go off to college, you end up with a ton of time as well. But there’s about a 15-20 year window in the middle part of your life where it feels like there’s no time at all.

And I’ve been in that window since I was 28 years old, and I suspect I won’t leave that window until I’m around 50 years old. (Your window obviously depends on how many kids you have. I was 28 for our first kid and our youngest, as I said above, is six years old now.)

So at around the age of fifty, I think I’ll probably look around and realize that it’s pretty much just my wife and me again. And I’ll be like, “What do you want to do now?”

Right now, my wife controls a huge percentage of our social calendar because she’s on the mom circuit and she has a ton of friends out there. Now that all three of our kids are in school all day long, she’s got the freedom to hang out with them. This is kind of an early window for what life is like when your kids are adult and they’re independent.

But if you were in my house, you’d hear me say this every morning after my radio show is over: “What do I need to know about today?” Because my wife knows everything the kids have scheduled, she knows what we have scheduled. I focus on my work, and that’s pretty much it during the day. After my TV show, when the kids are home from school, I typically pivot to them.

I spend, conservatively, 95% of my limited free time with my kids. That’s going out to dinner or watching movies, attending their sporting events, driving them to their social obligations. I just don’t have very much time for friends or other family, to be honest.

It sounds like you’re still able to spend a decent amount of time with your friends, which is great. But I think when your time is limited, you have to prioritize. So are you actively rejecting opportunities to hang with your brothers now? Do they have families of their own? If they do, do your kids regularly play with each other? I guess what I’m getting at is this: would they say you are ignoring them or do they feel like your relationship is weak? If not, I wouldn’t obsess over the status of the relationship right now.

But if you really feel like it’s an issue, I’d have a conversation with your brothers about at it at the next family event. My bet is they’re busy too and feel fine about their relationship with you.

“I’m 34, married with a 6-year-old kid. We live near my mom and have a great relationship with her. She does a lot for our family and loves to watch our daughter and even have her over for sleepovers. It’s great. 

Every year at Christmas she hounds both my wife and I for a gift list for us. Like we’re 9 years old again. I get it- she wants to give us stuff and is able to. And I don’t wanna sound like we don’t appreciate it because we do. But I kinda have everything I want or need. And I’m hard to buy for. Besides, the element of surprise is her favorite part so if I tell her what I want, I know what I’m getting. 

How do I tell her to just buy stuff for our kid? Am I being unreasonable?”

Every time I eat dinner with my parents, my dad tries to give me $20 or $40 after dinner.

That’s despite the fact that I’m getting close to making more in a week than my dad ever did in a year.

But I still take the money.

And I still let him pick up the check at dinner.

Because he’s my dad and no matter what I do in life, I’ll always be his son.

And, you know what, if my three boys grow up to all turn into Elon Musk and become wildly successful billionaires, I’ll still insist on picking up the check when we go out to dinner. Because I’m their dad.

Having said that, I’ve been through this Christmas gift mess. And basically what I’ve settled on is telling everyone, “I don’t need anything, spend whatever you would spend on me to give the kids more toys.”

They don’t always listen, but it keeps them from feeling compelled to ask me what I want and it keeps me from having to come up with something that I need (which I don’t actually need).

I buy books on Amazon, and I’ll buy things every now and then at Costco because I like shopping there. But otherwise I’m not much of a consumer.

Personally, I think it’s a good feeling to know you don’t need anything, but if you did, you could just go buy it yourself.

So that’s kind of how I handle Christmas.

“Hey Clay, I’m currently a sophomore in college. When it was time for me to go to college, I felt like I had my life basically planned out on where I wanted to go and what I wanted to do.

I got into a good school, and decided to go my own direction out of state. From there I decided I’d go through school and try and work my way up the ladder in the sports world. I really felt like I had things set up.

Fast forward 18 months, and that’s all changed. The prospect of working in sports has completely faded as I’ve begun to see how the industry works from the inside. Additionally, I realized I immensely undervalued the friendships I created from grade school to high school, and being away from all of them while they mainly attend the in-state colleges sucks. I’m still closer with them than any of my new out of state friends, and realize I probably never should have left in the first place.

The problem is I did, and it’s somewhat difficult to move back given housing and admissions situations in the current scope of the world. Add in a lack of sense of direction for my future, along with all of the lockdowns and it’s left me depressed and unsure of where to go. How do you recommend I try to go about things in hopes of just finding some sort of happiness and direction again?”

First, I know exactly how you’re feeling.

I went away to college my first year and considered transferring back closer to home for college because I wasn’t happy that first year. I even went through the transfer process, was accepted at the new school, and then had to decide during the summer what direction I was going to take for my sophomore year.

In my case, I went to George Washington University my freshman year, really didn’t like it that much, and applied to transfer to the University of the South at Sewanee. So I considered going from one extreme to the other, a large city school to extremely small and rural liberal arts school.

One of my best high school friends went there, and I almost made the decision to transfer. But ultimately I didn’t pull the trigger and stayed in college at George Washington. And every year got better after that freshman year.

And I think that was an important decision because it toughened me up quite a bit.

Ultimately I decided not to transfer because I think a big reason I wasn’t happy was because I was homesick. That is, it wasn’t the university itself, it was just being away from home. And the good thing about being homesick is the more time you spend away from home, the less homesick you get.

I think we vastly under-rate how many college kids who go pretty far away from home are homesick. And if you are really homesick, that can turn into depression. That’s because college life can be pretty lonely.

I think these are common experiences.

So what did I change my sophomore year? I ensured I was super busy. I had a job. I had an internship in Congress. I had all of my usual school obligations, and I also set a goal of graduating in three years, which I did. I think sometimes having a lot of free time can make you obsess over things in a way you don’t do if you are super busy.

So I got busier.

And that helped me quite a bit.

By midway through my sophomore year, everything was good for me and I didn’t have any issues from that point forward.

If I had college to do all over again, I think having one good friend going to the same school would have made things way better. Especially as a freshman. Not a girlfriend or boyfriend, by the way, I think that’s a bad idea. Just someone who is a connection to your previous life and is a good friend.

Then you could experience everything together.

I think if I’d had that, I wouldn’t have been anywhere near as homesick my freshman year.

But my situation is not the same as yours. And everyone is different. But I do think it’s important to know that what you’re experiencing is quite common for college kids who go away from home for their freshman years.

Good luck going forward.

As always send your 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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  1. How is Clay an expert on parenting? I have four daughters; the oldest is 30 and the youngest is 16. And there are four grandchildren in the picture as well. Young parents who have yet to get their kids through high school, college, job hunting, marriage, home ownership, and begetting their own children would be wise to withhold their pearls of wisdom.

    My wife and I never taught our children to believe in the social convention of Santa Claus, and our girls hopefully learned to be appreciative of what they received at Christmas time, birthdays, Valentine’s Day, Easter etc. Instead of ripping through every present recklessly and yet always wanting more or better things, our girls gave us a hug and kiss after opening each one.

    What did they lose by our “SPOILING THEIR FUN”? Nothing, there’s nothing to spoil if you don’t teach the lie to begin with. If my girls didn’t like the presents, it was MY fault. Plus they wouldn’t throw a fit with Santa in the mall the following year! Maybe you’ve never seen that scene.

    And how does Clay know that a little lie about Santa does not intrinsically affect a child’s belief in a parent’s honesty? For some parents, having their children be appreciative is more important than using Santa as a threat in case they’re naughty. Just like parents use the “I’ll call the cops on you” because they cannot discipline their own children.

    It seems that even adults need this magical outside agent to make everything ok. Stretching that concept out it even more…well then Santa is The Government, ready to hand out freebies if we cast the right ballot and make sure our Christmas list is a good one. And we always want more; it’s never enough. If ten years old is the “right” age to tell kids the truth about Santa, when is the “right” age to tell adults the truth about Uncle Sam?

    The sex education analogy is absurd. Babies are a natural outcome of natural relations between men and women. Questions WILL be asked by children and SHOULD be asked? But Santa Claus is a fabrication that we propagate. There is nothing natural or even supernatural involved. Relating the two scenarios is not remotely similar. Santa is not a ‘complex issue’ because it’s a non-issue. Babies are something else entirely.

    I like Clay’s sports analyst hat, his lawyer hat (those articles are particularly good), and his entrepreneurial hat. But as far the child psychology and parent advising hat?…Put that one on in 20 years.

  2. Dear Sexchange Insurance Dad,

    I say go for it. Maybe just have kid wear a dress to school one day, or post a pic on Insta or FB wearing fingernail polish – ON THE WAY TO THE DRIVING TEST!!!

    That way you can both later legitimately claim that well, that’s how youngster was feeling that day, and after all, it’s all about FEELINGS, right? not stupid facts like having a penis.

    If Junior suddenly decides at age 22 (or 25) that he/she is pretty dang heterosexual and likes being male again, who’s to say there’s anything wrong with that? Isn’t that what all the wokesters are for, anyway? just depends (literally) on which side of the bed you wake up on that day?

    No bothersome hormone shots. No messy “re-assignment” surgery. No therapy. Just “identify” and everything is peachy and no one can say boo. Otherwise, they are intolerant fascists. Guess that mean ol insurance company can’t complain.

    I’d suggest selecting PROGRESSIVE since they are least likely to be able to call you out on this later. If anyone is “gender fluid” it’s that creepy-ass Flo.

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